1 This case concerns a dispute over the validity of the testator’s (“Deceased”) fifth and final will, executed on 26 November 2020 when he was 92 years old, less than three months before his death. The Deceased’s grandson challenges the will on three grounds: that the Deceased lacked testamentary capacity; that he did not know and approve of its contents; and that it was procured by undue influence.

2 By November 2020, the Deceased had been diagnosed with Parkinson’s disease with cognitive decline and had experienced episodes of memory loss, hallucinations and delusions. The Deceased’s biological son who received a substantially greater benefit under the fifth and final will, was involved in preparing a typewritten note recording the proposed amendments, and the fifth will was executed at his residence. The will writer was not legally trained, and aspects of the fifth will were based on purportedly erroneous legal advice or inaccurate information concerning the ownership of the Deceased’s properties.

3 Having considered the evidence as a whole, I find that the Deceased retained the requisite testamentary capacity, understood and approved the dispositive provisions of the fifth and final will, and was not under any undue influence at the time of execution. The fifth and final will is therefore valid.

4 The Deceased, born in 1928, was the patriarch of the family. He passed away on 15 February 2021 at the age of 93. ¹ In his lifetime, he carried on the business of trading in leather, shoes and shoe components and undertook property investments. This was done through a sole proprietorship known as the “Corporation” and four private limited companies (“Companies”):

The Corporation and the Companies are collectively referred to as the “Businesses”.

5 The Deceased was married to his wife (“[M]”), who is presently still alive. However, [M] has had dementia for several years and was certified to have lost mental capacity on 7 August 2020. ² They have three biological children and one adopted son, listed below in seniority of age: ³

6 [C1] has two sons from her first marriage — the elder son, [GS1], and the younger son, [GS2] (“1st Defendant”). When she remarried, both children were left to the care of their grandparents, ie, the Deceased and [M]. The 1st Defendant moved in with the Deceased and [M] in 2001 when he was 11 years old, while [GS1] had already been staying with the Deceased and [M] sometime before. ⁴ The Deceased and [M] thus helped to raise the 1st Defendant and [GS1]. ⁵ [C1] has been estranged from the family since 2001 and is presently residing in Thailand. ⁶

7 The Deceased was highly successful in his endeavours, ⁷ allowing him to amass a sizeable fortune and purchase a total of 11 properties, which I have listed below in chronological order by the month and year of their purchase: ⁸

8 There are two neighbouring properties — [Property L] and [Property D] (collectively, the “Neighbouring Properties”) — central to this dispute.

9  During his lifetime, the Deceased executed a total of five wills: ⁹

10 At the time Ms Ng prepared the 1st, 2nd and 3rd Wills, she had also prepared and attended to the execution of three corresponding wills by [M] (“Mirror Wills”). The terms of [M]’s wills mirrored or were very similar to those of the 1st, 2nd and 3rd Wills of the Deceased in relation to the specific bequests to be given to each beneficiary. ¹⁰ Sometime after the execution of the 3rd Will and [M]’s corresponding mirror will, [M]’s dementia worsened and no subsequent will was executed by her.

11 In late 2020, the Deceased contacted his nephew, [N]. [N] worked for the Deceased for more than a decade since 1977 and thus developed a close bond with the Deceased. The Deceased sought [N]’s assistance to look for someone to help with drafting his 5th Will, which was to become his last will and testament as he passed away less than three months later. He wanted someone who was fluent in the Teochew dialect and could attend before him in person. Since [N] had at the time recently engaged SimplyWills Pte Ltd to help with drafting his mother’s will, he recommended the same to the Deceased. ¹¹

12 On 26 November 2020, [N] brought Mr Tan and Mr Tan’s wife, Mdm Tan Soo Huang (“Mdm Tan”), from SimplyWills Pte Ltd to [Property B], where the Plaintiff was residing. The Deceased was present and Mr Tan began taking instructions in the Teochew dialect from the Deceased for the purpose of drafting the 5th Will. From time to time, [N] excused himself to use the washroom and walked in and out of the house to take phone calls. ¹² The contents of the 5th Will were explained by Mr Tan in the Teochew dialect in the presence of Mdm Tan. ¹³ The attesting witnesses to the 5th Will were Mr Tan and Mdm Tan. ¹⁴

13 On the same day, prior to executing the 5th Will, the Deceased executed a Lasting Power of Attorney (“LPA”). Mr Tan served as the translator. Ms Boey Souk-Tann (“Ms Boey”), an advocate and solicitor who practised at Legal Standard LLP at the material time, was the independent certificate issuer. She was accompanied by her colleague, also an advocate and solicitor, Mr Bhagwandas Mahtani (“Mr Mahtani”). ¹⁵ The Plaintiff was appointed as the sole donee. ¹⁶

14 In the 1st Will, the Deceased appointed [M] as his sole executrix and trustee and bequeathed to her, amongst others, all his real and personal property upon trust to deal with, in her absolute discretion. ¹⁷

15 In the 2nd and 3rd Wills, the Deceased again devised and bequeathed to [M] all his real and personal property. ¹⁸ However, in the event that [M] predeceased him, the Deceased specified how each substantial asset owned by him was to be divided amongst the respective beneficiaries, namely his four children, [GS1] and the 1st Defendant. A clause in both the 2nd and 3rd Wills provided that the shares comprised in and the assets owned or held by the Businesses be held on trust and managed by the Plaintiff and 2nd Defendant for a period of 11 years following the date of the Deceased’s death (“11-Year Trust”). The income therein was to be divided in the manner as stipulated in the will. The reason for the 11-Year Trust, as expressly stated in the 2nd and 3rd Wills, was to ensure that the Deceased’s children live harmoniously with one another for years after the Deceased’s and [M]’s demise. ¹⁹ In the 3rd Will, the Deceased also made a specific cash bequest of S$1,603,076.90 each to the 2nd and 3rd Defendants.

16 On 12 June 2020, the Deceased executed the 4th Will. There were several material changes made: ²⁰

(a) The Deceased bequeathed all his shares, rights and interests in his Businesses to the Plaintiff, the 2nd Defendant and 3rd Defendant absolutely in the proportions stipulated therein. In particular, the Plaintiff was to inherit the largest proportion (ie, 100% of the Corporation, 55% of [Company B] and 40% of the remaining Companies). ²¹

(b) The provision for the cash bequests was removed.

(c) The provision for the 11-Year Trust was deleted.

Of significance is the fact that pursuant to the 2nd, 3rd and 4th Wills, the 1st Defendant was to inherit [Property L] and [GS1] was to inherit [Property D].

17 For avoidance of doubt, the Deceased and [M] had other grandchildren (ie, the children of the Plaintiff, the 2nd and 3rd Defendants) ²² who were not provided for in any of the five wills. The 2nd to 4th Wills also contained a clause providing that any beneficiary who disputed any term, contested the validity of or initiated any legal proceedings concerning the will would be given only $10,000 in assets and their inheritance would be forfeited (“No Contest Clause”). ²³

18 On 26 November 2020, the Deceased executed the 5th Will. It provided that the Plaintiff was to inherit all the Deceased’s shares, rights, title estate and interests in the Corporation, [Company B] and [Company D]. The remaining Companies were to be divided equally among the Plaintiff, the 2nd Defendant and the 3rd Defendant. ²⁴

19 Crucially, the devises to the 1st Defendant and [GS1] were swapped. Under the 5th Will, the 1st Defendant was to receive [Property D] if [M] predeceased the Deceased, while [GS1] was to receive [Property L]. As [Property D] was held in joint tenancy by the Deceased and [M], [M] became its sole owner by survivorship upon the Deceased’s death. The conditional devise of [Property D] to the 1st Defendant therefore did not take effect. In addition, under the terms of [M]’s will, [GS1] was named as the devisee of [Property D]. Thus, the 1st Defendant received neither of the Neighbouring Properties from the Deceased’s estate, while [GS1] received [Property L] and was also bequeathed [Property D] under [M]’s will. The only other provision made for the 1st Defendant under the 5th Will was a half-share of the balance, if any, of a $500,000 cash gift to [C1] which was to be paid out in monthly maintenance of $3,000 during [C1]’s lifetime. ²⁵

20 The 5th Will appointed the Plaintiff as the sole executor. ²⁶ The No Contest Clause was also expressly included in the 5th Will. ²⁷

21 The 2nd Defendant originally had a good relationship with the Deceased. She helped the Deceased out with his various Businesses, acting as the “hands” to the Deceased’s “brain”. ²⁸ However, the Deceased’s relationship with the 2nd Defendant deteriorated significantly by the time the 5th Will was executed on 26 November 2020.

22 The main source of their conflict was the intended sale of [Property M], one of the properties jointly owned by the Deceased and [M]. Sometime after [M] lost mental capacity, the Deceased decided to sell [Property M], but the 2nd Defendant, acting as the donee of [M], refused. She felt a need to protect her mother’s assets and did not wish to “sign anything” to sell her mother’s assets. She also felt that [M] would not have agreed to the sale of [Property M] because it was where the family spent many happy moments when they were young. ²⁹

23 Thereafter, lawyers were engaged and the Deceased and the 2nd Defendant began communicating via lawyer’s letters:

(a) On 20 October 2020 (which was about five weeks before the Deceased made his 5th Will), the Deceased convened a meeting at an accounting firm. Amongst those present at the meeting were the Plaintiff, the 2nd and 3rd Defendants and some officers from the accounting firm. The subject of the meeting was the distribution of industrial properties held by [Company B]. The 2nd and 3rd Defendants objected to the Deceased’s decision to give the factory properties to his children and defied the Deceased openly at the meeting and in the presence of others who were not family members, which angered him. ³⁰

(b) On 7 November 2020 (which was about three weeks before the Deceased made his 5th Will), Eden Law Corporation wrote letters to the Plaintiff and the Deceased on behalf of the 2nd Defendant, expressing concerns that the Plaintiff had been “exerting undue pressure and influence” on the Deceased. It also stated that the attempt to sell [Property M] was “against the interests of [M]” and proposed that the Deceased undergo a mental capacity assessment by a qualified medical professional to be appointed jointly by the Plaintiff and the 2nd Defendant. ³¹

(c) On 13 November 2020 (which was about two weeks before the Deceased made his 5th Will), Legal Standard LLP replied on behalf of the Plaintiff, asserting that a medical specialist had already certified that the Deceased was mentally capable. The letter also stated that the Deceased was prepared to meet the 2nd Defendant in the presence of solicitors and the Plaintiff, so that the 2nd Defendant could independently assess his mental capability. ³²

(d) On 24 November 2020 (which was two days before the Deceased made his 5th Will), Eden Law Corporation wrote back to Legal Standard LLP, seeking a copy of the mental capacity assessment performed by the Deceased. The letter further stated that the 2nd Defendant was concerned about the influence of the Plaintiff on the Deceased and for that reason, she had asked the Deceased to submit to a mental capacity assessment. ³³

(e) On 8 December 2020, Legal Standard LLP replied (more than a week after the Deceased made his 5th Will), stating again that the Deceased was already certified by a medical specialist to have full mental capacity and that there was no reason for the Deceased to provide the 2nd Defendant with a copy of such an assessment, or seek to be independently assessed. ³⁴

24 After the execution of the 5th Will, the Deceased continued to pursue the sale of [Property M]. He also terminated the 2nd Defendant’s employment and evicted her from his property at [Property C]:

(a) On 12 January 2021, Legal Standard LLP wrote a letter on behalf of the Deceased, informing the 2nd Defendant that the Deceased had found a prospective buyer for [Property M] and sought her signature for the draft option for sale. ³⁵

(b) On 15 January 2021, Allen & Gledhill LLP (the law firm which the lawyer representing the 2nd Defendant had changed employment to) responded to Legal Standard LLP’s letter, stating that the 2nd Defendant did not agree to the sale. ³⁶

(c) On 18 January 2021, the Deceased sent the 2nd Defendant another letter through Legal Standard LLP, evicting her from [Property C]. She and her family members were to vacate the property by 8 February 2021. ³⁷

(d) On 2 February 2021, the 2nd Defendant’s part-time employment with [Company B] and [Company C] was terminated. ³⁸ On the same day, the Deceased made a police report against the 2nd Defendant for illegal intrusion into the offices of the family businesses after her termination. ³⁹

(e) On 5 February 2021, the Deceased sent the 2nd Defendant another eviction letter through Legal Standard LLP, reminding her to vacate the property at [Property C] by 8 February 2021. ⁴⁰

25 In August 2015, the Deceased was examined by Dr Tay Kay Yaw (“Dr Tay”) at the National Neuroscience Institute (“NNI”). The initial clinical impression was “Essential Tremor with superimposed mild parkinsonism features”. He was prescribed a trial of Madopar to address his slowness of movements. ⁴¹ On 20 October 2015, the Deceased underwent a medical examination by Dr Adrian Wang (“Dr Wang”) of Dr Adrian Wang Psychiatric and Counselling Care, who found no major psychiatric disorder or cognitive impairment and certified the Deceased as fit to write or amend his will. ⁴²

26 For the next four years, the Deceased maintained stable cognitive function. Regular appointments with Dr Tay showed that his memory remained stable without decline. The Deceased was also stable motor-wise and he maintained independence in his daily activities. In December 2018 and January 2019, Dr Wang confirmed the absence of major psychiatric disorders or cognitive impairment and certified the Deceased’s continued fitness to make testamentary decisions. ⁴³

27 In late August 2019, [M] pushed the Deceased, causing him to fall and hit his head on the floor. The Deceased was hospitalised and received three stitches. When Dr Tay examined the Deceased on 7 November 2019, whilst his memory remained stable with no decline, his movements had become slower than normal. Dr Tay increased his Madopar dosage to manage the slowness in his movements. ⁴⁴ Nonetheless, the Deceased’s cognitive function appeared to remain intact, as evidenced by a medical examination performed by Dr Paul Ho (“Dr Ho”) of Ho Medical Centre Pte Ltd in April 2020. Dr Ho observed the Deceased to have functional cognition after being tested for dementia and mental capacity. ⁴⁵

28 On 9 July 2020, the Deceased was diagnosed with Parkinson’s disease with cognitive decline by Dr Xu Zheyu (“Dr Xu”) of NNI. He started taking Rivastigmine to control his hallucinations and to slow down the decline of memory loss. ⁴⁶ Slightly more than two weeks later, on 24 July 2020, the Deceased attended a medical examination by Dr Yeo Seem Huat (“Dr Yeo”) who certified that he was of “sound mind, and able to take care of his own affair[s]”. ⁴⁷

29 On 16 September 2020, the Deceased fell down in his home. He underwent a Magnetic Resonance Imaging scan and two X-rays at Mount Alvernia Hospital. They showed “[n]o acute infarct or evidence of acute intracranial haemorrhage” but revealed “[s]evere chronic white matter microvascular ischaemic changes and marked age-appropriate involutional changes”. ⁴⁸

30 On 12 November 2020 (which was some two weeks before the 5th Will was made), Dr Yeo provided another medical memo, certifying again that the Deceased was of “sound mind” and “able to take care of his own affair[s]”. ⁴⁹ When examined by Dr Tay on 10 December 2020 (which was about two weeks after the 5th Will was made), the Deceased himself acknowledged to Dr Tay that there had been instances of confusion. Dr Tay wrote in his medical report dated 15 January 2021 that the Deceased had experienced hallucinations, though the Deceased retained insight and the hallucinations were not troublesome. Dr Tay noted that the Deceased was “stable clinically” and did not require any changes to his medication but would need continued follow-up for his Parkinson’s disease and monitoring of his cognition. ⁵⁰

31 On 21 January 2021 (which was about two months after the 5th Will was made), Dr Yeo examined the Deceased and noted that he was “stable and rational” and opined that the Deceased was “of sound mind, able to take care of his own affair[s]”. ⁵¹

32 Less than a month later, on 15 February 2021, the Deceased died of coronary artery disease. ⁵²

33 On 22 February 2021, the Plaintiff applied for a Grant of Probate vide HCF/P 73/2021 using the 5th Will. On 12 March 2021, the 3rd Defendant filed a caveat and served it on the Plaintiff. The 3rd Defendant subsequently withdrew the caveat on 16 April 2021. Three days later, the 1st Defendant filed a caveat (HCF/CAVP 9/2021) and served it on the Plaintiff. On 1 June 2021, the 1st Defendant filed a Citation to Propound the Will and served it on the Plaintiff.

34 The court directed the Plaintiff to file and issue a writ of summons to propound the 5th Will pursuant to rr 252 and 253 of the Family Justice Rules 2014. As such, this suit commenced on 22 June 2021.

35  The Plaintiff’s case is that the Deceased: ⁵³

36 The Plaintiff relies on the fact that the two doctors (Dr Ho and Dr Yeo) who examined the Deceased in respect of his mental capacity in the course of 2020 and 2021, had testified to his functional cognition and sound mind. The 5th Will was prepared by Mr Tan, a will planner who had drafted approximately 800 wills for his clients. At least ten of these clients were Teochew-speaking. ⁵⁴ The Plaintiff explains that the Deceased did not want Ms Ng to prepare his 5th Will for him as Ms Ng had been willing to allow the 2nd and 3rd Defendants to “see her for their purpose of trying to interfere with [the Deceased’s] personal decisions relating to his assets”. Moreover, the Deceased suffered from severe scoliosis which inhibited his mobility to travel to Ms Ng’s office. According to the Plaintiff, as [GS1] had been residing in [Property L] as his matrimonial home, the Deceased decided to leave this property to [GS1]. ⁵⁵

37 Crucially, the Plaintiff says that the Deceased decided to leave a greater share of the assets to him because the Deceased’s relationship with the Defendants had deteriorated significantly by the time the 5th Will was executed on 26 November 2020 (see [22]–[24] above). Against this backdrop, the Plaintiff argues that the 5th Will represents the wishes of the Deceased. As such, the Plaintiff seeks a declaration that the 5th Will is valid. He also wants an order that the caveat lodged by the 1st Defendant in HCF/CAVP 9/2021 be removed and that a Grant of Probate be issued to himself.

38 The 1st Defendant avers instead that: ⁵⁶

39 In essence, the 1st Defendant says that the Deceased had already exhibited instances of memory loss indicative of symptoms of cognitive impairment, as well as hallucinations and delusions indicative of symptoms of psychosis. The main pieces of evidence relied upon are contemporaneous audio recordings of the Deceased and his family members. ⁵⁷ The 5th Will was irrational and could not truly reflect the Deceased’s wishes and intentions. In particular, the Deceased wanted to ensure that all his children and his two grandsons (ie, the 1st Defendant and [GS1]) were “fairly and adequately provided for”. ⁵⁸ He further contends that the 5th Will was “executed surreptitiously and under suspicious circumstances”. Finally, he avers that the Plaintiff “capitalised on [the Deceased’s] mental and physical [frailties] to procure his execution” of the 5th Will. ⁵⁹

40 Accordingly, the 1st Defendant seeks a pronouncement against the 5th Will propounded by the Plaintiff as the true and valid last will of the Deceased. He wants, instead, a declaration that the 3rd Will, or alternatively, the 4th Will, is the true and valid last will of the Deceased, and that the Plaintiff is entitled to only $10,000 as his bequest thereunder. Lastly, he asks that the Grant of Probate of the 3rd Will, or alternatively, the 4th Will, be issued to the 2nd Defendant.

41 For the avoidance of doubt, the 2nd and 3rd Defendants are not contesting the validity of the 5th Will.

42 There are several main issues before the court:

43 Although the evidence relevant to these issues overlap, testamentary capacity, knowledge and approval, and undue influence are distinct legal inquiries governed by different principles.

44 The applicable legal principles may be summarised as follows (Chee Mu Lin Muriel v Chee Ka Lin Caroline [2010] 4 SLR 373 (“Muriel Chee”) at [39]–[49]; Ng Bee Keong v Ng Choon Huay [2013] SGHC 107 (“Ng Bee Keong”) at [65]):

(a) The legal burden is on the propounder of the will to prove that the testator possessed testamentary capacity. This is prima facie established by the due execution of the will in ordinary circumstances where the testator was not known to be suffering from any kind of mental disability. However, the mere fact that the testator was suffering from some type of mental disability does not necessarily mean that he had lacked testamentary capacity. A testator may still retain sufficient mental capacity to appreciate the testamentary act, understand and approve the terms of the will when executing it even if his mental power is reduced by physical infirmity or the decay of advancing age to below the ordinary standard.

(b) Once testamentary capacity has been established, a rebuttable presumption arises that the testator knew and approved of the contents of the will at the time of execution. In ordinary circumstances, the evidential burden of proof shifts to the opponent of the will to rebut this presumption.

(c) However, the presumption does not arise where there were circumstances surrounding the execution of the will which would raise a well-grounded suspicion that the will (or some provision in it) did not express the mind of the testator. The propounder of the will must then produce affirmative evidence of the testator’s knowledge and approval.

(d) What affirmative evidence is required in each case will depend upon the circumstances of the case. The greater the degree of suspicion, the stronger the affirmative proof must be to remove it.

45 For a will to be found valid, the testator must: (a) have the mental capacity to make a will; (b) have knowledge and approval of the contents of the will; and (c) be free from undue influence or the effects of fraud. The essential requirements of testamentary capacity are as follows (Muriel Chee at [37]):

46 The capacity to make a will may vary depending on the complexity of the testator’s affairs and family situation, and on whether the will is a simple or complicated one (ULV v ULW [2019] 3 SLR 1270 (“ULV v ULW”) at [25]).

47 The legal burden is on the Plaintiff to prove that the Deceased possessed testamentary capacity. The Plaintiff seeks to establish his case by relying on the testimonies of various factual witnesses who have had the chance to interact with the Deceased, the evidence and reports of certain doctors who had examined and conducted tests on the Deceased, as well as the Plaintiff’s expert witness, Prof Kua Ee Heok (“Prof Kua”).

48 On the other hand, the 1st Defendant maintains that the Deceased lacked testamentary capacity to execute the 5th Will. This is evidenced by the Deceased’s irrational will, the fact that he suffered from memory loss, the various hallucinations and delusions that were indicative of the Deceased’s cognitive impairment and psychosis during the material time. The 1st Defendant further relies on the evidence and reports of certain doctors who had examined and conducted tests on the Deceased and his expert witness, Dr Tan Sheng Neng (“Dr Tan”), to argue that the Deceased likely suffered from dementia.

49 The ultimate question is not whether the Deceased can retrospectively be assigned a particular medical diagnosis. It is whether, on 26 November 2020, he understood that he was making a will and its consequences, had a sufficient appreciation of the property he was disposing of, could appreciate the claims of the potential beneficiaries, and was free from any abnormal state of mind which distorted his judgment. I consider first the alleged irrationality and blatant error in the 5th Will, followed by the evidence of the Deceased’s cognitive symptoms, the medical evidence and the factual evidence of his functioning at the material time.

50 An indication of testamentary capacity would be the rationality of the will having regard to its terms and the identities of the beneficiaries (Muriel Chee at [40]). The 1st Defendant submits that no presumption of testamentary capacity can arise in respect of the 5th Will because the terms are clearly irrational: ⁶⁰

(a) First, [M] had been completely excluded as a beneficiary under the 5th Will. This is in contrast to the 1st to 3rd Wills, in which she was the sole beneficiary of all the real and personal property of the Deceased.

(b) Second, in contrast with the 3rd and 4th Wills under which the Deceased appointed more than one executor and trustee, only one executor and trustee (ie, the Plaintiff) was appointed under the 5th Will.

(c) Third, the terms of the No Contest Clause in the 5th Will were drafted to allow the Plaintiff to distribute the forfeited inheritance at his sole discretion, potentially allowing him to escape the consequences of his own dispute of the 5th Will.

(d) Fourth, the effect of the 5th Will is such that none of the Neighbouring Properties would be devised to the 1st Defendant under the 5th Will if the Deceased predeceased [M] (which is what eventually happened). This is despite the fact that the Deceased had all along intended for each of the two Neighbouring Properties to be devised to each of the two grandsons raised by him — ie, the 1st Defendant and [GS1].

51 Moreover, the Deceased had made a “patently incorrect” distribution of his single largest asset, [Property K], a good class bungalow by wanting to split it into three equal parts of 40% among three beneficiaries (“40/40/40 Distribution”). ⁶¹ This made no arithmetic sense as it would have amounted to more than 100%.

52 I disagree with the 1st Defendant that the 5th Will is irrational. I will address each argument in turn. Even though there is no provision for [M] under the 5th Will, it must be borne in mind that the Deceased held eight out of eleven real properties in joint tenancy with [M]. I further note that [Property K], the good class bungalow, the largest and most valuable of all the eleven properties, was held in joint tenancy with [M]. Upon the Deceased’s death, [M] became the sole registered proprietor of seven jointly held properties and came to hold a 40% share of [Property G], by survivorship. The existence of the large number of jointly held properties, forming the substantial portion of the value of the estate of the Deceased, provides in my view a rational explanation for the omission of a further testamentary gift to [M]. The appointment of the Plaintiff as sole executor is also in my view not inherently irrational. By November 2020, the Deceased’s relationship with the 2nd Defendant had deteriorated to such an extent that lawyers had to be engaged and the Deceased and the 2nd Defendant were communicating via lawyer’s letters (see [23] above). Although the Deceased had appointed both the Plaintiff and the 2nd Defendant to be the executors and trustees of his 4th Will, it is not at all surprising to me that he had consciously decided to remove the 2nd Defendant as the executor and trustee from his 5th Will and have the Plaintiff as his sole executor and trustee in his 5th Will in view of the bad relationship that had developed between himself and the 2nd Defendant by the time he was executing his 5th Will. Furthermore, the Deceased had by this time placed greater trust in the Plaintiff. Whether the Deceased’s preference for a sole executor and trustee for his 5th Will is wise or fair is not the question; it is capable of rational explanation on the evidence before me.

53 As for the terms of the No Contest Clause, the original phrasing suggested by the Deceased did not specify what would happen to any forfeited inheritance if a beneficiary challenged the will. Mr Tan advised the Deceased that there would be a “gap” if the No Contest Clause was triggered because the forfeited inheritance would end up as an intestacy clause. ⁶² The Deceased then accepted Mr Tan’s advice to insert a proviso allowing the executor to distribute the forfeited inheritance at his absolute discretion (“Absolute Discretion Proviso”). ⁶³ I make no finding on whether the advice given by Mr Tan is legally correct. The fact that the Deceased considered and accepted a suggestion made by the will writer is evidence of his ability to think for himself and exercise judgment. The Plaintiff had prepared a note typewritten in Chinese dated 22 November 2020 at the Deceased’s instructions (“Typewritten Note”). ⁶⁴ It recorded the Deceased’s intended changes to the 4th Will. Even so, the Deceased did not simply hand the Typewritten Note over to Mr Tan as his instructions for the drafting of his 5th Will. He made certain decisions and changes, including insisting on the inclusion of the No Contest Clause, which showed his testamentary capacity and his independent thinking and decision making. The 40/40/40 Distribution was an arithmetic error and is relevant to the assessment of capacity. It is not, however, determinative when considered in isolation; its significance must be assessed together with the Deceased’s functioning across the testamentary exercise as a whole.

54 Next, the 1st Defendant raises the following incidents to show that the Deceased suffered from memory loss, hallucinations and delusions:

(a) In May 2020, the Deceased reported that some relatives came to his house and he was worried that they would go into his room. ⁶⁵

(b) On 6 July 2020, the Deceased experienced hallucinations of the family’s domestic helper and an unknown man going upstairs in his residence. ⁶⁶

(c) On 9 July 2020, the Deceased was examined by Dr Xu who diagnosed him with Parkinson’s disease with cognitive decline. He was prescribed medication to control his hallucinations and slow down the decline of his memory loss. ⁶⁷

(d) On 13 July 2020, the Deceased insisted that he had wanted to appoint three donees under his LPA executed on 12 June 2020 even though the Plaintiff was named the sole donee. ⁶⁸

(e) On 20 July 2020, the Deceased could not recall having executed the 4th Will or the bequests that he had made or removed therein. ⁶⁹

(f) On 23 July 2020, the Deceased and the 2nd Defendant had a conversation where the Deceased suggested that [M] renew her driving licence even though she was 82 years old and had not driven for several years by then. ⁷⁰

(g) On 13 September 2020, the Deceased reported seeing people entering his residence to remove rubbish and tree branches. ⁷¹

(h) On 21 September 2020, the Deceased reported seeing people digging a tunnel underground at his residence and workers using his water. ⁷²

(i) On 14 October 2020, the Deceased spoke of specific shops for rent, even though said shops were owned by the Deceased’s father and had been compulsorily acquired in the 1980s. ⁷³

(j) On 5 November 2020, the Deceased was unable to recognise his own residence and reported seeing a woman running up to the third floor of his residence. ⁷⁴

(k) On 24 November 2020, the Deceased told the 2nd Defendant that he did not want to keep frogs or purchase so many frogs. ⁷⁵

55 On 12 June 2020 (the same day on which the 4th Will was executed), the Deceased also executed an LPA, in which he appointed the Plaintiff as sole donee in respect of both his personal welfare and his property and affairs. The LPA was submitted for registration on or about 17 June 2020. When it was subsequently brought to the Deceased’s attention on or about 13 July 2020 that he had appointed only one donee under the LPA, he denied this and insisted that he had wanted to appoint three donees or replacement donees under the LPA. In light of this, the application was eventually withdrawn on or about 15 July 2020. ⁷⁶

56 Most of the conversations are evidenced by audio recordings from devices secretly installed by the Defendants in the Deceased’s residence. ⁷⁷ The 1st Defendant explains that they installed the recording devices because the 1st Defendant and the domestic helper noticed that the Plaintiff “came surreptitiously late at night” and “only left in the early hours of the morning” in July 2020 to speak to the Deceased. They were worried about the Plaintiff’s agenda and the fact that the Deceased was starting to exhibit memory loss. ⁷⁸

57 The Plaintiff states that on 10 December 2020 (about two weeks after the 5th Will was executed), the 2nd Defendant brought the Deceased for a medical review, during which Dr Tay gave a favourable review of the Deceased’s mental condition. This was heard by the 2nd Defendant and the Plaintiff, both of whom were present during this medical review by Dr Tay. ⁷⁹ The Plaintiff admits that the Deceased experienced hallucinations but maintains that they were only a side effect of the medication he took. ⁸⁰

58 The medical cause of the Deceased’s symptoms is relevant but not determinative. The central question is whether, whatever their cause, his cognitive impairment, memory difficulties, hallucinations or delusions prevented him on 26 November 2020 from understanding his testamentary act, appreciating the extent of his estate and the claims of the potential beneficiaries, or making his dispositions free from an abnormal state of mind.

59 The Deceased had taken three Mini-Mental State Examinations (“MMSEs”) on 1 February 2018, 20 April 2020 and 9 July 2020 respectively. The first was conducted by a nurse and the Deceased scored 17/30. ⁸¹ The second was conducted by Dr Ho and the score was 25/30. ⁸² The third was performed by a nurse at the same consultation when the Deceased was assessed by Dr Xu. The score was 17/30. ⁸³

60 The MMSE is the most commonly used screening tool for cognitive impairment and dementia worldwide. ⁸⁴ It comprises a series of questions posed to the patient — some which test the patient’s awareness of their surroundings (eg, “What time is it?”, “What area are we in?”), and some which test their immediate recall, delayed recall and sentence repetition. ⁸⁵ The maximum attainable score is 30/30. In a National University of Singapore validation study of MMSE among Singapore seniors in 2007, it was concluded that a score of 23/30 and below would signify abnormal cognition. However, Prof Kua caveated that none of the patients in the study was 90 years old or more and thus the results cannot be extrapolated to the Deceased. ⁸⁶

61 Prof Kua’s view is that the Deceased’s memory problems, hallucinations and delusions were the side effects of his medications, namely Madopar and Lyrica. ⁸⁷ Prof Kua is an Emeritus Professor of Psychiatry at the Yong Loo Lin School of Medicine and Emeritus Consultant Psychiatrist at the National University Hospital. Prof Kua explained in his expert report that Madopar (which the Deceased had been consuming) is commonly prescribed for patients with Parkinson’s disease to improve movement of the limbs but it releases dopamine into the brain, which can stir up symptoms of hallucination, delusion and confusional state.

62 Prof Kua maintains that the degree of the Deceased’s cognitive decline was not indicative of dementia. He doubts the scores of 17/30 in the MMSEs performed in February 2018 and July 2020. A year after the MMSE in February 2018, Dr Wang found no evidence of cognitive impairment and two weeks after the MMSE in July 2020, Dr Yeo’s examination of the Deceased provided some evidence that the Deceased could appear orientated and coherent during brief clinical consultations. Prof Kua also asserts that it is important to know if the nurses who administered the tests were trained on how to use the MMSE. ⁸⁸ In any event, Prof Kua states that the diagnosis of dementia is not just through the MMSE, but a “whole catalogue of symptoms” and a physical examination by the doctor. ⁸⁹ Prof Kua also drew attention to the Deceased’s retention of moral judgment — Dr Tay had asked the Deceased during the medical examination on 10 December 2020 (which was about two weeks after the execution of the 5th Will) about borrowing money from a loan shark and robbing from a bank, to which the Deceased reprimanded him. ⁹⁰

63  Prof Kua further observes that the five doctors who treated the Deceased during his lifetime — Dr Wang, Dr Ho, Dr Yeo, Dr Tay and Dr Xu — never made a diagnosis of dementia. Prof Kua’s opinion is that Dr Tan, who had never met the Deceased, was “incorrect” to boldly claim that if the Deceased were diagnosed with dementia, the MMSE would suggest moderately severe dementia. Rather, the Deceased had Parkinson’s disease with mild cognitive impairment and no evidence of dementia. ⁹¹ In sum, notwithstanding the side effects from the medication, Prof Kua concluded at para 32 of his report that on 26 November 2020, the Deceased “had Testamentary Capacity to execute his Last Will”. ⁹²

64 The 1st Defendant challenges the impartiality, correctness, reliability and integrity of Prof Kua’s opinion. He argues that Prof Kua has failed to consider highly relevant information and evidence. For instance, Prof Kua did not address the evidence of Mr Tan who was directly involved in the will-making process. It was the Plaintiff’s counsel, Mr Yeo, who had informed Prof Kua of the specific areas he had to look into. Separately, Prof Kua was also of the view that the Deceased “knew the [P]resident of China was Xi Jinping” when this question was posed to him by Dr Tay during a consultation on 10 December 2020. This was despite the fact the Deceased replied, “Lee, Lee what” and failed to give the correct answer despite repeated prompting. Eventually, it was the Plaintiff who said “Xi Jinping”, which the Deceased parroted. The 1st Defendant relies on this to impugn Prof Kua’s evidence, casting doubt on whether Prof Kua had properly reviewed the documents which formed the basis of his opinion. ⁹³

65 Dr Tan is of the view that the Deceased suffered from dementia and at para 14.8 of his report he stated that the Deceased “lacked testamentary capacity when he did his last will”. ⁹⁴ Dr Tan is a consultant psychiatrist at Tan Chue Tin Clinic, Paragon Medical Centre. He is also a visiting consultant to Dover Park Hospice and Lions Nursing Home for the Elders. ⁹⁵

66 Dr Tan notes “complaints of severe memory loss, hallucinations, and delusions, indicating a decline in his cognitive state”, as well as observations that the Deceased was “not mentally alert”. ⁹⁶ He points out that the Deceased had only scored 17/30 on the MMSE in February 2018 and July 2020. ⁹⁷ Dr Tan also says that the score of 25/30 in April 2020 could nevertheless reflect cognitive impairment because the Deceased should not be expected to score anything less than 28/30. This view is supported by a study on the Singapore Chinese population which posits that anyone with at least a secondary school education should not score below 28/30 on the MMSE. Although the Deceased only had a primary school education, he was a highly successful businessman who would have, in Dr Tan’s opinion, received the equivalent of a secondary school education if he had the opportunity to do so. ⁹⁸

67 Based on the conversation between the Deceased and the Plaintiff on 20 and 21 July 2020, Dr Tan observes that the Deceased exhibited a poverty of speech. This refers to a lack of speech, often reflecting a disruption in the thought process. During conversations, the Deceased’s replies were very sparse, brief and lacked spontaneity. ⁹⁹ He cites a Canadian study which states that no patient, regardless of diagnosis, is deemed to have capacity if their MMSE score is below 20/30. Relying on a local report mapping local MMSE scores to the severity of dementia, Dr Tan estimates that a score of 17/30 corresponds to moderate dementia. ¹⁰⁰ Hence, Dr Tan’s opinion is that the hallucinations were not merely a side effect of the Deceased’s medication — though he also notes that if the Deceased had adhered to the prescribed dosage of all his medication in the days leading up to and including 26 November 2020, there is a real possibility that their combined side effects would have negatively impacted the Deceased’s mental state. ¹⁰¹

68 Dr Tan also places weight on the fact that the Deceased instructed Mr Tan to distribute one of his properties into three portions of 40%. He would not have expected such a mistake to come from an astute businessman. ¹⁰² Dr Tan further criticises the swap of the Neighbouring Properties as a failure of high-level judgment as the Deceased failed to question why he was changing a decision he made consistently in the past. ¹⁰³ In Dr Tan’s view, the Deceased had suffered from a decline in his cognitive state from July to December 2020 such that he “lacked testamentary capacity” as at 26 November 2020. ¹⁰⁴

69 The Deceased consulted Dr Yeo on four occasions: 24 July 2020, 12 November 2020, 16 December 2020 and 21 January 2021. ¹⁰⁵ During these visits, he did not conduct MMSEs. Instead, he conducted “basic tests” comprising two to three questions to determine whether the Deceased was orientated to place and date, and whether he could do simple mathematical calculations. ¹⁰⁶ These tests were not made for the purpose of ascertaining whether the Deceased had the necessary mental capacity to make a will or an LPA, ¹⁰⁷ though Dr Yeo later clarified that such tests have in the past been relied upon and “accepted by the [c]ourt and the lawyer” for the purposes of certifying a person fit to make an LPA. ¹⁰⁸

70 During cross-examination, Dr Yeo was made aware of certain recordings evidencing the Deceased’s hallucinations and the fact that the Deceased forgot he made the 4th Will slightly more than a month after its execution (see [54(e)] above). Dr Yeo conceded that if such recordings had been brought to his attention at the material time, he would have formed a very different opinion and conclusion on the Deceased’s mental state and cognitive ability. ¹⁰⁹ Dr Yeo would also have expressed serious concerns as to the Deceased’s ability to manage his own affairs, and would not have come to the conclusions which he did in his three reports that the Deceased was “of sound mind, able to take care of his own affair[s]”. ¹¹⁰ He further agreed that the scores of 17/30 in the MMSEs were failing scores and were signs that the Deceased lacked cognitive ability and function. ¹¹¹

71 Dr Ho conducted an MMSE for the Deceased on 20 April 2020, in which he scored 25/30. During the trial, Dr Ho testified that the MMSE is a simple and low-sensitivity screening test which does not say much about a person’s mental capacity. Someone who fails the MMSE may have mental capacity, and someone who passes the MMSE may not have mental capacity. ¹¹² Instead, to confirm the presence of mental capacity, one needs to see a psychiatrist. ¹¹³ He further explained that a score greater or equal to 24/30 indicates “functional cognition” — ie, that the patient is “able to function within a normal capacity”. While functional cognition is part of mental capacity, it is not equivalent to mental capacity because mental capacity entails much more than that. ¹¹⁴

72 The 1st Defendant says that the medical report prepared by Dr Ho should be disregarded as the consultation took place seven months prior to the execution of the 5th Will. Similarly, the medical report prepared by Dr Yeo dated 24 July 2020 ought to be disregarded since it was prepared four months before the execution of the 5th Will. ¹¹⁵

73 Moreover, the 1st Defendant points out that the contents of Dr Yeo’s three medical reports are “almost identical”, which suggests that they were based on a standardised template. There is no information on exactly what tests, if any, were conducted on the Deceased, nor any observations made of the Deceased during the consultations. Neither is there any assessment of testamentary capacity. This may be contrasted against the medical reports of Dr Wang whom the Deceased had consulted in October 2015 and January 2019 for the purposes of the 2nd Will and 3rd Will respectively. In both, there is an explicit conclusion that the Deceased was “fit to write, or amend, his Last Will and Testament”. This is based on Dr Wang’s observations of the Deceased, including the Deceased’s ability to identify his properties and where they were located, and how many bank accounts he had. ¹¹⁶

74 Dr Tay and Dr Xu were not called as witnesses. However, the 1st Defendant relies on the observations made by Dr Tay and Dr Xu in the medical reports to substantiate his position that the Deceased had no testamentary capacity by the time of the execution of the 5th Will.

75 In a medical report dated 2 December 2020, Dr Tay diagnosed the Deceased with “Parkinson Disease with Cognitive decline”. ¹¹⁷ This diagnosis was based on the Deceased’s consultation with Dr Xu on 9 July 2020, during which Dr Xu had noted the 2nd Defendant’s complaint that the Deceased “has had memory loss that needed her to repeat herself multiple times and he had also hallucinations and delusions which caused stress to the family”. The Deceased was hence prescribed Rivastigmine to improve cognitive function and reduce hallucinations. ¹¹⁸

76 On 10 December 2020, the Deceased consulted Dr Tay again. He asked the Deceased who the President of China was, to which the Deceased struggled to answer despite frequently watching Chinese news. It was only after the Plaintiff prompted the Deceased with “Xi Jinping” that the Deceased repeated the answer. ¹¹⁹ In the circumstances, the 1st Defendant asserts that the medical evidence supports the position that the Deceased lacked mental capacity. ¹²⁰

77 Much of the disagreement between the experts centres around whether the Deceased suffered from dementia. Before analysing the comparative merits of each expert’s evidence, it should first be clarified that dementia is not determinative of testamentary capacity (or the lack thereof). The diagnosis of dementia would affect a testator’s mental capacity but it does not equate to a loss of testamentary capacity. Dementia is a progressive illness, which may not affect the testator’s mental faculties to the extent that he or she lacked testamentary capacity at an early stage of illness. The testator may also have had moments of lucidity during which he or she would have possessed testamentary capacity to execute a will (Muriel Chee at [50]). Given the fluctuations and lucid intervals of patients suffering from dementia, evidence which conclusively shows that within a few days of the testamentary act a person was incapable of making a will does not necessarily prove that they were incapable at the time they actually made it (Theobald on Wills (Alexander Learmouth et al eds) (Sweet & Maxwell, 20th Ed, 2025) (“Theobald”) at para 4-040). Persons with an underlying degree of dementia are particularly susceptible to temporary loss of capacity due to infections, certain medications, exhaustion, unfamiliar surroundings and the like, which may adversely affect their cognitive performance (Theobald at para 4-040). Conversely, the absence of dementia does not mean that the testator possesses testamentary capacity. There are many factors that may cause one to temporarily lose testamentary capacity. Prof Kua himself agrees that the side effects of the medication could well impair one’s mental capacity. ¹²¹

78 The experts had at various points in their respective reports expressed their individual views on the presence or absence of the Deceased’s testamentary capacity. ¹²² It is important to bear in mind that the role of medical experts in a case like this is usually to assist the court on the medical facts relating to the testator’s functions, such as diagnosis, symptoms, effect of medication, what an MMSE score does or does not show, and whether the observed condition was medically capable of affecting the testator’s ability to understand, recall and reason. The question of testamentary capacity is reserved for the court to answer. This is evident from the Court of Appeal’s holding in Muriel Chee at [42]:

79 Having analysed the evidence from both experts, I prefer the evidence of Prof Kua to Dr Tan. This preference is directed to their respective overall approaches and ultimate conclusions. It does not mean that I accept every aspect of Prof Kua’s evidence without qualification.

80 First, I find Prof Kua’s overall analytical approach more persuasive. Prof Kua appropriately treats the MMSE as a screening tool which could not, by itself, establish dementia. He also correctly notes that the diagnosis of dementia requires a “whole catalogue of symptoms” and a physical examination by the doctor. By contrast, Dr Tan places substantial weight on the MMSE scores and applies the relevant benchmarks in a manner which I find speculative. In particular, his opinion that the Deceased should have been expected to score at least 28/30 is premised on the assumption that, although the Deceased had received only a primary school education, his business success meant that he should be treated as having attained the equivalent of a secondary-school education. There is insufficient basis for that assumption. Moreover, Dr Tan’s view in his later report dated 4 March 2026 is that if the Deceased had been diagnosed with dementia, the MMSE score would indicate that he had moderate dementia. ¹²³ The word “if” suggests tentativeness and hedging, instead of an assertive opinion. We have no answer from Dr Tan as to what the MMSE score would suggest if no dementia was diagnosed.

81 Second, Prof Kua’s opinion is more consistent with the medical evidence from the Deceased’s attending doctors. None of the doctors who examined or treated the Deceased during his lifetime diagnosed him with dementia. Dr Tay and Dr Xu recorded cognitive decline, memory difficulties and hallucinations, but did not diagnose dementia. Dr Tay subsequently recorded on 10 December 2020 (about two weeks after the execution of the 5th Will) that the Deceased was orientated to time, place and person and was “stable clinically”, albeit that his cognition required continued monitoring. ¹²⁴

82 I recognise that Dr Yeo’s examinations were brief, were not directed at testamentary capacity (which he was not wrong not to have opined on given that question is strictly for the court to decide) and were conducted without his having been informed of the recordings relied upon by the 1st Defendant. Nevertheless, Dr Yeo’s contemporaneous observations provide some evidence that the Deceased was capable of appearing orientated and coherent during the clinical consultations. Considered together, his medical opinion stated in his medical records is more consistent with Prof Kua’s conclusion than with Dr Tan’s opinion that the Deceased had dementia of such severity that he would have basically lost his mental capacity by November 2020.

83 Turning to the specific instances relied upon by Dr Tan, I do not find them persuasive in proving the Deceased’s lack of testamentary capacity:

(a) As regards the 40/40/40 Distribution, I would not consider that the singular arithmetic error, when considered with other evidence, demonstrates a failure of one or more elements of testamentary capacity. As astute a businessman as the Deceased was, he was however already over 90 years old by 2020.

(b) The swap of the Neighbouring Properties also does not show a lack of high-level judgment. It made sense to the Deceased because [GS1] had in 2016 made [Property L] his matrimonial home. [GS1] maintained it at his own expense, including furnishing the home with household and electrical appliances as well as paying for the renovation. Sometime in 2020, [GS1] moved from [Property L] to a Housing Development Board flat. [GS1] rented [Property L] out and asked if he could keep the rental income to support his new growing family, to which the Deceased agreed. The Deceased was also happy that [GS1] had produced their first great grandson and that [GS1]’s wife was expecting a second child. ¹²⁵ Since [GS1] had already been managing [Property L] for some time and had paid for its renovation, it made sense for the Deceased to eventually bequeath that property to him. This was a considered and contextually rational decision.

84 I accept that there are shortcomings in some aspects of Prof Kua’s evidence. In particular, his report does not address Mr Tan’s evidence on the will-making process, and his understanding of the exchange concerning the President of China is inaccurate. The inability of the Deceased to name the President of China is relevant evidence of memory difficulty, although I do not consider it determinative of a lack of testamentary capacity. I also accept that the two MMSE scores of 17/30 warrant greater scrutiny. However, the nurses who administered the assessments were not called, and the evidence does not establish their relevant training, the circumstances in which the MMSEs were administered or how the individual scores were derived. The scores must therefore be treated with caution. They support the conclusion that the Deceased had experienced some cognitive decline, but do not establish dementia or want of testamentary capacity.

85 Next, I address the medical evidence from the doctors whom the Deceased consulted during his lifetime.

86 To the extent that Dr Yeo examined the Deceased on multiple occasions and certified him to be “of sound mind” and “able to take care of his own affair[s]”, the assistance his evidence provides is limited. Dr Yeo’s examinations were not directed at assessing mental capacity or diagnosing dementia. They were basic assessments confirming that the Deceased was orientated to place and date. Similarly, Dr Ho’s administration of the MMSE in April 2020 is not particularly helpful. Dr Ho himself acknowledged that the MMSE is a simple and low-sensitivity screening test that does not indicate much about a person’s mental capacity.

87 Moreover, Dr Tay’s diagnosis of Parkinson’s disease with cognitive decline is not the same as a diagnosis of dementia, and as I have already observed above at [77], even a diagnosis of dementia would not in itself establish a loss of testamentary capacity. Dr Tay himself had also given a favourable review of the Deceased’s condition during the consultation on 10 December 2020 (just two weeks after the execution of the 5th Will). He recorded that the Deceased acknowledged instances of confusion and retained insight. Dr Tay also observed that the Deceased’s hallucinations were not troublesome and the Deceased was orientated to time, place and person and “stable clinically”. ¹²⁶ Although Dr Tay was not called as a witness, his medical reports serve as contemporaneous medical records of Dr Tay’s observations of the Deceased just two weeks after the execution of the 5th Will.

88 Taken as a whole, the medical evidence from the Deceased’s treating doctors indicates that the Deceased suffered some degree of cognitive decline but does not establish that the Deceased had lost testamentary capacity by the time he executed the 5th Will on 26 November 2020.

89 There is no doubt that the Deceased had experienced some episodes of hallucinations, memory loss and delusions. I am inclined to take the view that these symptoms were side effects of his medication and were not permanent in nature. In addition to Prof Kua’s views, this deduction is backed by a medical note issued by Dr Yoon Kam Hon dated 23 July 2021, wherein it was confirmed that the Deceased was on medication which caused “occasional hallucinations”. ¹²⁷ The 1st Defendant himself conceded that the hallucination episodes occurred only about 15% of the time. ¹²⁸

90 Nonetheless, it is unnecessary to conclusively identify the cause of the Deceased’s symptoms — whether they were due to medication, Parkinson’s disease, an underlying cognitive disorder or some combination of these matters. The relevant question is the effect of those symptoms on the Deceased’s functional abilities at the time of the testamentary act. Was there any cognitive impairment or abnormal state of mind which affected his ability to satisfy the requirements of testamentary capacity at the time of the Deceased’s execution of the 5th Will? This is ultimately a question that none of the doctors is well-placed to answer, as none of them had the opportunity to interact with the Deceased personally on 26 November 2020. This brings me to the broader point about the limits of expert evidence in this context.

91 The evidence of experts should not be held to outweigh that of eye-witnesses who had opportunities for observation and knowledge of the testator. The court must consider the totality of the evidence as a whole, comprising both factual components (including evidence of friends and relatives who had the opportunity to observe the testator) and medical components (Muriel Chee at [38]). In circumstances such as the present, the evidence of those present when the testator gave instructions for the will is of considerable weight (Theobald at para 4-040). It is to that evidence that I now turn.

92 The Plaintiff maintains that the Deceased retained testamentary capacity on 26 November 2020. He noted that the Deceased read Chinese newspapers daily, was fully aware of his assets and made independent, calculated decisions. For instance, the Deceased intentionally removed cash bequests in the 5th Will because he had already used those funds to purchase a condominium for his children. ¹²⁹

93 The 1st Defendant points out that the Plaintiff himself had doubted the Deceased’s mental capacity on previous occasions. On 20 July 2020, the Plaintiff and the Deceased had a conversation:

(a)  The Plaintiff said to the Deceased that the Deceased’s previous solicitor, Ms Samantha Poo, had declined the engagement to prepare the Deceased’s will because she felt that the Deceased was “mentally… not so alert” and hence she did not dare make changes to the will. ¹³⁰ During cross-examination, the Plaintiff challenged the translation of this recording, clarifying instead that the actual term he used in Teochew was “jeng sim bo ho” which correctly translates to the Deceased’s “mood is no good”. ¹³¹

(b) The Plaintiff told the Deceased, “Even [Ms Ng] doesn’t want to do it. That’s why [Ms Ng] always rushes you, and ask[s] you to hurry up, hurry up, because you’re too long-winded. Because you don’t remember anything. Every time you’ll bring along the same document, and ask the same thing every time you visit. You ask the same question at every appointment. So much time is waste[d].” ¹³²

(c) When discussing about taking a test with a psychiatrist to prove capacity for making a will, the Plaintiff told the Deceased, “You’re confused lor…”, to which the Deceased replied, “Ya I’m confused”. ¹³³

(d) The Plaintiff said to the Deceased, “[Y]ou … are growing older year after year, and your mind is deteriorating over the years”, and “[i]f you keep dragging this out, by then, you might not even remember my name.” ¹³⁴

(e) The Deceased expressed confusion and the Plaintiff replied, “Yes if you feel confuse[d], then it means you are ineligible to make a will. Right? If you have lost your mental capacity, how can you make a will?” ¹³⁵

94 On 3 November 2020, the Plaintiff and the Deceased had another conversation:

(a) The Plaintiff said to the Deceased, “I see you are always sleeping. If you keep sleeping, I think you will develop dementia. Not good.” ¹³⁶

(b) The Plaintiff said to the Deceased, “No wonder [the 3rd Defendant] said your mind is not in good condition. You cannot manage matters anymore. Every meeting you say you are sleeping. You go to a meeting and come home ‘blur-blur’. And I explain, explain, and explain to you so many times. And you still don’t understand. That’s why [the 3rd Defendant] said you have dementia. You can’t manage work anymore”. ¹³⁷

95 The 1st Defendant further argues that the Plaintiff’s testimony on his lack of knowledge of the arrangements for the execution of the 5th Will is incredible. In essence, the Plaintiff’s evidence is that he only got to know that the Deceased had made an appointment with Mr Tan to make a new will on 26 November 2020 itself, when Mr Tan turned up at his doorstep. ¹³⁸ The 1st Defendant says that this is unbelievable given that the agreed location of the appointment was the Plaintiff’s residence. Further, this is contradicted by the evidence of Mr Tan (who said that the appointment was made several days before 24 November 2020) ¹³⁹ and [N] (who said that the Plaintiff was informed “closer to the date of the appointment”). ¹⁴⁰

96 [N]’s evidence is that the Deceased was “100% fine”, mentally sharp and had a daily habit of reading Chinese newspapers to stay abreast of current affairs and world politics. ¹⁴¹ According to [N], the Deceased requested for a will writer who was fluent in Teochew. The Deceased also insisted on drafting the will without any pressure or interference from his children. [N] thus recommended Mr Tan, a Teochew-speaking will writer who could attend to the Deceased at home. [N] even suggested to the Deceased that if he was not comfortable with the draft done by a layperson, he could always take it to a law firm thereafter to “change the letterhead”. ¹⁴² [N] noted that the Deceased was “very prepared, determined not to make any more mistake[s]” with the drafting of the 5th Will. ¹⁴³

97 The 1st Defendant casts doubt on [N]’s credibility. He says that it was the Plaintiff, with the assistance of [N], who had surreptitiously arranged for the 5th Will to be prepared by Mr Tan. The location was [Property B] because the 1st Defendant was residing at [Property K] and the 2nd Defendant would drop [M] off at [Property K] every day at that time. The Plaintiff thus chose his own residence (ie, [Property B]) for the execution of the 5th Will to avoid triggering the Defendants’ suspicions. ¹⁴⁴

98 Further, the 1st Defendant says that [N]’s explanation that he recommended the services of Mr Tan to the Deceased because Mr Tan did his mother’s will is unconvincing. [N] was aware that unlike his own mother, the Deceased owned multiple properties and businesses and had many potential beneficiaries. [N] had previously brought the Deceased to consult various lawyers and even accompanied the Deceased to see Mr Mahtani. Yet, [N] claimed during cross-examination that it did not even cross his mind to recommend the services of a lawyer for the drafting of the 5th Will. [N] was also cognisant of the dispute that had already arisen between the Deceased’s children by that time and ought to have considered that engaging a lawyer to draft the will would have been the most prudent option. Therefore, according to the 1st Defendant, [N]’s conduct “defies logic and belief”. What really happened was that [N] acted at the behest of the Plaintiff, who prevailed upon him to recommend a layperson with no legal training or qualification to execute the 5th Will “at all costs”. ¹⁴⁵

99 When Mr Tan first met the Deceased on 26 November 2020 to take his instructions on the making of the 5th Will, he was given a copy of the Deceased’s existing will (ie, the 4th Will) and “another piece of paper with [the Deceased’s] intended changes”, which was the Typewritten Note. ¹⁴⁶ The Typewritten Note was drafted by the Plaintiff purportedly at the Deceased’s instructions.

100 Despite the Typewritten Note, Mr Tan took instructions directly and verbally from the Deceased (see [129] below). ¹⁴⁷ Mr Tan systematically ran through the 4th Will with the Deceased, verifying the ownership details of each property and confirming if there were any changes to who it was intended to be given to. ¹⁴⁸ During this process, the Deceased referred to the Typewritten Note on certain occasions and did not on others. ¹⁴⁹ The Deceased would nod his head or say “si” or “tio” (in the Teochew dialect) or “okay”, which Mr Tan took to mean that the Deceased understood and agreed with what he had said. ¹⁵⁰ Mdm Tan corroborated Mr Tan’s testimony, testifying that the Deceased confirmed he was alert and aware of what was happening. ¹⁵¹

101 The Deceased even negotiated the professional fees for the will-writing service after the 5th Will was finalised and executed. ¹⁵² The Plaintiff contends that the fact that Mr Tan was unaware of the Deceased’s medical history (including his diagnosis of Parkinson’s disease and purported cognitive decline) ¹⁵³ reinforces the fact that the Deceased was lucid at the material time and showed no sign of confusion. ¹⁵⁴ I note that [N]’s evidence is that the Plaintiff had left before the making of the will, ¹⁵⁵ whereas Mr Tan recalled that the Plaintiff and [N] were occasionally in the room during the session. ¹⁵⁶ That discrepancy however does not undermine Mr Tan’s clear evidence that all instructions regarding the contents of the 5th Will came exclusively from the Deceased. ¹⁵⁷ Mr Tan also only recalled seeing [N] in the room during the actual signing of the 5th Will. ¹⁵⁸

102 The Plaintiff argues that any debate over the correctness of Mr Tan’s legal advice regarding the purported “gap” in the event the No Contest Clause is triggered is a “peripheral issue”. What is material is that the Deceased had the mental acuity to agree to insert the Absolute Discretion Proviso. Similarly, any “errors” in the 5th Will were only a result of Mr Tan “faithfully recording the instructions given by [the Deceased]”. ¹⁵⁹

103 Ms Boey and Mr Mahtani attended at [Property B] also on 26 November 2020, the same day that the 5th Will was to be executed. Though Mr Mahtani was the one who received the initial instructions on what the Deceased intended, Ms Boey was instructed to go with Mr Mahtani to assist with certifying the LPA. ¹⁶⁰ Ms Boey acted as the independent certificate issuer for the LPA executed by the Deceased. She spoke in Mandarin and Mr Tan translated her words to Teochew for the benefit of the Deceased. The execution of the LPA preceded the execution of the 5th Will.

104 Ms Boey testified that the Deceased appeared to have had “a plan” and was quite “definite”, sounding like he had already considered matters. Although he was “a bit weak”, there was no influence of any kind from anyone — he was alert, lucid and could verbalise his thoughts. ¹⁶¹ Ms Boey also did not sense any impairment of the Deceased’s mental faculties throughout the session. ¹⁶² Ms Boey could not recall many details from the session but she opined that it was “more likely” that the digital forms and standard checkboxes in the LPA document were filled up prior to her arrival at [Property B]. When she arrived, she asked the Deceased who he was choosing as the donee and he said that he wanted to appoint his son. ¹⁶³

105 Mr Mahtani explained during cross-examination that he was approached by the Deceased sometime during November 2020 before the execution of the LPA. He recalled that the Deceased was “very upset when he got a letter from his daughter” (see [23(b)] above), ¹⁶⁴ and described his daughter as “tamak” (“greedy” in Malay). ¹⁶⁵ The Deceased and the Plaintiff came to Mr Mahtani’s office, and Mr Mahtani took their instructions to respond to the lawyer’s letter from the 2nd Defendant. The Deceased did most of the talking. Although he was old and frail, he was “mentally sharp” and “coherent”, and they conversed in both Malay and English. ¹⁶⁶ The Deceased expressed in Malay that he had faith in the Plaintiff. ¹⁶⁷ The Deceased also told Mr Mahtani that the 2nd Defendant and several other family members were “spying on him” and that he wanted to kick the 2nd Defendant out of his property. ¹⁶⁸ It is significant to note that the Deceased did in fact take follow up action after his execution of the LPA and his 5th Will on 26 November 2020 to evict the 2nd Defendant and her family from his property at [Property C] and he further terminated the 2nd Defendant’s part-time employment with [Company B] and [Company C] (see [24(c)]–[24(e)] above).

106 Sometime later in November 2020, around the time when the Deceased received a second lawyer’s letter from the 2nd Defendant (see [23(d)] above), the Deceased attended at Mr Mahtani’s office again and gave instructions to prepare an LPA which named the Plaintiff as his donee. After Mr Mahtani prepared the LPA document, the Plaintiff called Mr Mahtani to confirm the date and time for the signing of the LPA. Mr Mahtani then brought Ms Boey along on 26 November 2020 to serve as the certificate issuer as she could speak Mandarin. ¹⁶⁹ On the day, Mr Mahtani stood “about 4, 5 metres away” while Ms Boey reviewed the LPA document with the Deceased. ¹⁷⁰

107 The 1st Defendant argues that little to no weight ought to be placed on the evidence of Ms Boey and Mr Mahtani for several reasons:

(a) Mr Mahtani had acted for the Deceased and the Plaintiff in relation to the issue of the Deceased’s mental capacity to make important decisions relating to the disposition of his assets. Mr Mahtani had thus already taken a “firm and definite position” on the issue. ¹⁷¹ Mr Mahtani’s testimony that he could communicate with the Deceased in English and Malay is also incredible because: (a) the 2nd Defendant testified that the Deceased could only speak and understand very basic and “broken” English and Malay, certainly not to the extent of giving instructions or understanding the contents of letters; (b) Mr Mahtani himself had stated that the Deceased “only speaks the Teochew dialect” in a letter dated 8 December 2020; ¹⁷² and (c) Ms Boey was asked to assist Mr Mahtani with the LPA because Mr Mahtani did not speak Mandarin. ¹⁷³ Further, Mr Mahtani’s evidence was based on his bare recollection of events. He was not sure and could not remember if he had taken any contemporaneous notes of his meetings with the Deceased. ¹⁷⁴

(b) As for Ms Boey, she had very limited interactions with the Deceased and she too did not take any contemporaneous notes of her meeting with the Deceased on 26 November 2020. ¹⁷⁵

108 Next, I turn to the evidence of those who had interacted with the Deceased prior to and after 26 November 2020.

109 The 1st Defendant’s primary case is that the Deceased had dementia which caused him to lose testamentary capacity. Even if the Deceased did not have dementia, he suffered from memory loss, hallucinations and delusions from the medication he was taking such that he did not have testamentary capacity. Amongst others, the 3rd Defendant testified that the Deceased did not comprehend the LPA in July 2020 which appointed the Plaintiff as his sole donee. In fact, the Deceased had laughed and said, “No way I will do such a foolish thing”. ¹⁷⁶ The 2nd Defendant said the Deceased was a “puppet” whose brain was “not working very well”. ¹⁷⁷

110 The Plaintiff challenges the Defendants’ credibility in respect of the Deceased’s alleged lack of testamentary capacity:

(a) He states that the 1st Defendant “is inherently biased” given his admission to doing investigative work to gather evidence against the Plaintiff. ¹⁷⁸ The 1st Defendant had also conceded during cross-examination that the Deceased only experienced hallucinations about 15% of the time. ¹⁷⁹ Any allegations by the 1st Defendant that the Deceased was “not 100%” or “blur” and “hunched over” merely affirms the Deceased’s physical pains which did not affect his mental capacity. ¹⁸⁰

(b) As for the 2nd Defendant, the Plaintiff asserts that she had admitted to fabricating and manipulating evidence. For instance, although she initially claimed to have spoken to the Deceased personally about her eviction, she later said that he was “speechless” and never actually discussed it. ¹⁸¹ She also selectively extracted negative entries about the Plaintiff which she deemed relevant from [M]’s diary. ¹⁸²

(c) The Plaintiff points out that the 3rd Defendant’s act of initiating the revocation of the LPA in July 2020 highlights his “personal role” in the matter. ¹⁸³ Moreover, the 3rd Defendant, having been a full-time church worker since 2004, has no insight into the Deceased’s corporate or estate planning strategies. ¹⁸⁴

111 Ms Ng testified that the Deceased was “not even near demented” during the execution of the 4th Will in June 2020. ¹⁸⁵ Indeed, he was “very alert”, “very business savvy” and could identify all his properties as well as the occupants in each of them. ¹⁸⁶ The Deceased even informed Ms Ng that [M] was demented and unable to execute a mirror will. ¹⁸⁷

112 According to Ms Ng, the Deceased increased the Plaintiff’s share of the inheritance in the 4th Will because the Plaintiff had been following the Deceased in the business for the past 10 to 20 years. ¹⁸⁸ Prior to the execution of the 4th Will, the Deceased was “quite upset” with the Plaintiff as he wanted to migrate overseas. ¹⁸⁹ The Deceased also lamented to Ms Ng that the 2nd Defendant had “too much power” in managing his matters and “wanted too much control”. He was unhappy that the 2nd Defendant tried to control his finances and refused to tell him the balance in his own bank account. That was why the Deceased wanted the 4th Will to be kept a secret from her and for the Plaintiff to be named the sole donee of his LPA. ¹⁹⁰ At all times, the Deceased had confirmed that he wanted to gift each of the two Neighbouring Properties to each of the two grandsons, ie, the 1st Defendant and [GS1]. ¹⁹¹

113 Having considered the totality of the evidence of the factual witnesses, especially those who were present on the day of and at the execution of the 5th Will, I find that the Deceased possessed the requisite testamentary capacity on 26 November 2020 when he executed the 5th Will.

114 I am mindful that the Plaintiff stands to benefit the most from the 5th Will and thus has the greatest incentive to give evidence to advance his case that the Deceased retained testamentary capacity. It is clear to me that he was involved in the preparatory arrangements for the making of the 5th Will. He assisted the Deceased by drafting the Typewritten Note which recorded the Deceased’s intended amendments to the 4th Will. The 5th Will was also executed at the Plaintiff’s very own place of residence. It beggars belief that he was unaware of the will-making taking place in his own home until the day itself. In addition, the Plaintiff’s statements in the recordings at [93]–[94] are significant. They show that the Plaintiff himself perceived the Deceased as having intermittent problems with memory, repetition and comprehension, and I take them into account against the Plaintiff. They do not, however, establish the Deceased’s mental condition and state of mind on 26 November 2020 itself or show that he failed any requirement of testamentary capacity on that date. I therefore treat them as a reason for caution and place limited weight on the Plaintiff’s general assertions concerning the Deceased’s lucidity.

115 Turning to the testimonies of [N], Mr Tan, Mdm Tan, Ms Boey and Mr Mahtani, their evidence on their interactions with the Deceased on the day the 5th Will was executed is consistent and provides substantial support for my conclusion that the Deceased retained testamentary capacity at the time when the 5th Will was executed. [N] attested that the Deceased was “100% fine” and mentally sharp. Ms Boey testified that the Deceased appeared to have had “a plan” and was quite “definite”, sounding like he had already considered matters. She confirmed that there was no influence of any kind from anyone — he was alert, lucid and could verbalise his thoughts. Ms Boey, as a practising solicitor who specialises inter alia in wills, probate and trusts, also did not sense any impairment of the Deceased’s mental faculties throughout the session. Mr Mahtani corroborated this position. His explanation of the Deceased’s thought process (ie, that he was upset with the 2nd Defendant and that he believed in the Plaintiff) is entirely consistent with what other factual witnesses such as Ms Ng had said.

116 Importantly, none of the witnesses — [N], Ms Boey, Mr Mahtani, Mr Tan and Mdm Tan — are beneficiaries under any of the Deceased’s wills. None of them stand to gain from a finding that the 5th Will is valid. [N], in particular, did not have the best relationship with the Plaintiff due to historical work-related disagreements ([N] claims the Plaintiff had “sabotaged” him and gave him problems at work, causing him to resign), ¹⁹² which further reduces the likelihood that he would give false evidence in the Plaintiff’s favour. The consistency of their accounts accordingly lends their evidence considerable probative weight.

117 I disagree with the 1st Defendant that little to no weight ought to be placed on the evidence of Ms Boey and Mr Mahtani. I do not consider the inconsistency in the evidence concerning the languages spoken by the Deceased to render Mr Mahtani’s account inherently incredible. The 2nd Defendant accepts that the Deceased could speak and understand some English and Malay, although not to a level at which he could give detailed instructions or understand legal letters. ¹⁹³ Mr Mahtani’s evidence is not that the Deceased gave him detailed testamentary instructions in English or Malay. His evidence is that they conversed in those languages and that the Deceased was able to express matters such as his unhappiness with the 2nd Defendant and his confidence in the Plaintiff. Nor is that claim inconsistent with Ms Boey having been brought along as the independent certificate issuer for the LPA on 26 November 2020. The Deceased was more proficient in Mandarin than in English or Malay, and a Mandarin-speaking certificate issuer was therefore preferred for the formal LPA process, with Mr Tan translating Ms Boey’s Mandarin into Teochew. Mr Mahtani’s statement in his letter of 8 December 2020 that the Deceased “only speaks the Teochew dialect” is inaccurate if read literally. However, in light of the 2nd Defendant’s own evidence that the Deceased possessed some ability to communicate in English and Malay, I understand the real point to be that Teochew was the Deceased’s primary and most proficient spoken language, rather than that he was wholly incapable of communicating in any other language.

118 The 1st Defendant’s criticism is that Mr Mahtani had previously acted for the Deceased and the Plaintiff, and neither Ms Boey nor Mr Mahtani had taken contemporaneous notes of their interactions with the Deceased. While contemporaneous notes would likely have strengthened their evidence, the absence of such is not fatal. What matters is whether their evidence is credible, consistent and corroborated by the other evidence before the court. In this case, the evidence of both Ms Boey and Mr Mahtani is entirely consistent with the evidence of the other independent witnesses present on 26 November 2020. As for the 1st Defendant’s suggestion that Mr Mahtani had already taken a “firm and definite position” on the Deceased’s mental capacity by virtue of having previously acted for the Deceased and the Plaintiff, I do not consider this to be a basis to disregard his evidence. If anything, it reinforces Mr Mahtani’s view as he had multiple opportunities to interact with the Deceased before, on and also after 26 November 2020 (ie, the date of execution of the 5th Will). Mr Mahtani had to take instructions from the Deceased, amongst other things, not only for the LPA but also to respond to the lawyer’s letters from the 2nd Defendant and subsequently to evict the 2nd Defendant from his house and terminate her employment. Mr Mahtani would arguably be in an even better position than Mr Tan and Mdm Tan to attest to the Deceased’s mental faculties. In the circumstances, I find no reason to doubt the reliability of the evidence of Ms Boey, and more particularly, the evidence of Mr Mahtani.

119 I also reject the 1st Defendant’s suggestion that the Plaintiff had conspired with [N] to surreptitiously procure the execution of the 5th Will. [N] had nothing to gain from assisting with the procurement of the 5th Will. Moreover, [N] was not very close to the Plaintiff as they had a history of disagreements. [N] instead had deep respect and affection for his uncle, the Deceased. ¹⁹⁴ It was the Deceased who had, of his own accord, approached [N] in late 2020 and requested [N]’s assistance to find someone who was fluent in Teochew and could attend in person to assist the Deceased to prepare his 5th Will. Since [N] had at the time recently engaged SimplyWills Pte Ltd to help with drafting his mother’s will, he recommended the same to the Deceased. ¹⁹⁵ It was therefore [N], and not the Plaintiff, who directly arranged for Mr Tan’s engagement. Although the Plaintiff facilitated and participated in the preparation, Mr Tan confirmed that all instructions regarding the contents of the 5th Will came exclusively from the Deceased, and he only recalled seeing [N] in the room during the actual signing of the 5th Will. I am hence not satisfied that the alleged conspiracy has been proved.

120 The totality of the evidence from the witnesses who interacted with the Deceased on 26 November 2020, as well as the conduct of the Deceased himself, indicates to me that the Deceased had understood the nature of the testamentary execution of his 5th Will and its consequences, and had known the extent of his disposition and its beneficiaries. None of the witnesses present during the will-writing session observed the Deceased experiencing any overt episode of hallucination or confusion. More importantly, it has not been shown that any cognitive symptom or abnormal state of mind impaired his mental acuity and judgment.

121 Ms Ng’s evidence lends further force to my conclusion. Although her testimony pertains to her interactions with the Deceased in June 2020, her assessment of the Deceased being “very alert” and “not even near demented” is entirely consistent with the evidence of Mr Mahtani who interacted with the Deceased in the weeks leading up to and on the day of the execution of the 5th Will. It also corroborates the views of [N], Ms Boey, Mr Tan and Mdm Tan. While Ms Ng’s interactions with the Deceased in June 2020 predated the execution of the 5th Will by some five months, they are nonetheless relatively proximate in time and they provide a useful baseline against which the Deceased’s mental state may be assessed.

122 Importantly, Ms Ng was not involved in the drafting and execution of the 5th Will and has no interest in defending the propriety of the will-writing engagement. She played no role in the events of 26 November 2020. There is no reason for her not to give her evidence as objectively as she could and I find that she did so. As Ms Ng had acted as the Deceased’s solicitor over a number of years and had prepared multiple wills for him, she had sustained and repeated interactions with the Deceased over a fairly long period of time. She is well-placed to assess his mental state and would likely have been able to detect any signs of cognitive decline or dementia. Her unequivocal assessment that the Deceased was mentally alert and far from demented in June 2020 therefore carries substantial weight.

123 As for the 3rd Defendant’s argument on the Deceased’s memory loss as reflected in the Deceased’s insistence on or about 13 July 2020 on appointing three donees for his LPA and his denial that he had appointed only one donee for his LPA executed about a month earlier on 12 June 2020 (see [55] above), I do take this as an instance of the Deceased’s memory loss in my assessment which is reflective of the Deceased’s intermittent problems with his memory. However, one cannot extrapolate from the Deceased’s wishes in July 2020 for three donees for his LPA to suggest that he could not have intended some four months later on 26 November 2020 to appoint the Plaintiff as the sole donee for his fresh LPA and the Plaintiff as the sole executor and trustee of his 5th Will. Even if the Deceased might have been reluctant to appoint the Plaintiff as his sole donee in July 2020, this does not mean that his views on the matter were fixed and immutable. By November 2020, the Deceased had grown increasingly aggrieved with the 2nd and 3rd Defendants. With the help of the Plaintiff, the Deceased had discovered sometime around 17 November 2020 the recording devices secretly installed in his home, ¹⁹⁶ which he attributed to the 2nd and 3rd Defendants “spying” on him. ¹⁹⁷ Against this backdrop, it is entirely plausible that the Deceased had, over time, come to repose greater trust and confidence in the Plaintiff — whom he regarded as his “favourite child” ¹⁹⁸ by 26 November 2020 — and had accordingly changed his mind to appoint the Plaintiff as his sole donee for his LPA and also as his sole executor and trustee for his 5th Will. A change of mind under these circumstances is in my view consistent with the existence of mental capacity to make reasoned and rational decisions and to make them deliberately, and is not, without more, evidence of mental incapacity.

124 After assessing the totality of the evidence, I find that the Plaintiff has established each element of testamentary capacity:

(a) The Deceased understood that he was making a will which would govern the disposition of his estate upon death. He initiated the process of obtaining a Teochew-speaking will writer, reviewed successive drafts, selected his executor and insisted upon the inclusion of particular provisions.

(b) He had a sufficient appreciation of the general extent of his estate. He was able to discuss the Businesses and the various properties and could identify the intended beneficiaries. The errors concerning the ownership arrangement of certain properties and the 40/40/40 Distribution must be considered, but they do not, when viewed against the evidence as a whole, establish that he lacked any general appreciation of all the properties in his estate. The Deceased could accurately recall the manner of holding of all of his 11 properties save for [Property E]. In relation to [Property G], although his description of the precise legal form of ownership was inaccurate, he appears to have remembered that the property was held amongst five persons (see [147]–[148] below). In my view, that degree of recall is notable for a 92-year-old man diagnosed with Parkinson’s disease with cognitive decline.

(c) He knew the persons who might reasonably have claims upon his estate and was able to evaluate their claims. His decisions reflected his relationships with his wife, his children and his two grandsons, including his grievances against the 2nd and 3rd Defendants and his preference for the Plaintiff by November 2020.

(d) Although the Deceased had occasionally experienced hallucinations and apparently delusional episodes, it has not been shown that any abnormal belief distorted the dispositions made in the 5th Will. His belief that the 2nd and 3rd Defendants were “spying” on him had an objective basis as there were indeed recording devices secretly installed in his room without his knowledge.

125 Notwithstanding my finding of testamentary capacity, I agree with the 1st Defendant that there were certain circumstances surrounding the execution of the will which would raise a well-grounded suspicion that the 5th Will might not have expressed the mind of the Deceased.

126 To this end, it bears emphasis that there is a distinction between circumstances which raise a suspicion of testamentary incapacity and circumstances which raise a well-grounded suspicion that the will did not express the mind of the testator (XBP v XBO [2025] SGHC(A) 15 at [46]). Suspicious circumstances relevant to testamentary capacity are those that give rise to a grave suspicion of incapacity, such as where the testator suffers from mental disability or illness or where the terms of the will are incoherent, irrational or strange. In cases where other suspicious circumstances are raised, probate may be refused on the basis of lack of knowledge and approval by the testator (Ng Bee Keong at [46]–[47]). In Theobald at para 4-051, the learned editors raised several classic examples of suspicious circumstances. An oft-cited instance is where a person was active in procuring the execution of a will under which that person takes a substantial benefit, for example, by suggesting the terms of the will to the testator and instructing a solicitor chosen by that person.

127 Although the Plaintiff (who stands to benefit the most from the 5th Will) seeks to distance himself from the execution of the 5th Will, it appears to me that he was materially involved in the preparatory arrangements of the 5th Will (see [114] above). Amongst other things, he prepared the Typewritten Note, provided the venue and, contrary to his evidence, was probably made aware of the appointment with the will writer in advance. Around the same period, large sums amounting to over $1m were also transferred from accounts the Deceased jointly held with [M] into accounts jointly held with the Plaintiff (see [154] below). Additionally, the will writer was not legally trained and there were errors and unexplained annotations in the drafting process.

128 Considered cumulatively, these circumstances give rise to a substantial suspicion. The Plaintiff must thus produce cogent affirmative evidence that the Deceased understood and approved the dispositive provisions of the 5th Will.

129 According to Mr Tan, this was the process of the will-writing in relation to the 5th Will of the Deceased: ¹⁹⁹

(a) As he discussed with the Deceased, he made handwritten annotations on a copy of the 4th Will against the specific clauses which the Deceased wished to amend. ²⁰⁰

(b) Based on his handwritten annotations, he typed on his laptop and printed out the first draft of the 5th Will (“1st Draft”).

(c) He went through and explained the contents of the 1st Draft to the Deceased and made handwritten annotations on the 1st Draft against the specific clauses which the Deceased wished to amend.

(d) Based on his handwritten annotations on the 1st Draft, he amended the 1st Draft on his laptop and printed out the second draft of the 5th Will (“2nd Draft”).

(e) He went through and explained the contents of the 2nd Draft to the Deceased. He made handwritten annotations on the 2nd Draft to indicate that he had explained the specific clauses in the 2nd Draft, and also to indicate that the Deceased wanted to add the word “surviving” to the clause under the header “Provision of Substitute Beneficiaries”.

(f) When the Deceased indicated that he was fully satisfied with the contents of the 2nd Draft, he printed out the final version of the 5th Will which was executed by the Deceased.

130 Mr Tan’s account of the process is not, by itself, sufficient to dispel the suspicion. As I discuss below, the more probative evidence is that the Deceased made specific decisions and gave instructions which were not merely a wholesale adoption of the Typewritten Note (see [136], [137] and [149]). These matters reinforce the conclusion that the Deceased was mentally engaged with the dispositive scheme rather than merely assenting passively to words placed before him.

131 The provisions of the 5th Will relevant to [Property D] and [Property L] are as follows: ²⁰¹

132 The parties do not dispute that the Deceased had always intended, even during the execution of the 5th Will, to devise one Neighbouring Property each to the 1st Defendant and [GS1]. ²⁰² The 1st Defendant explains that he was supposed to inherit [Property L] while [Property D] was to go to [GS1], the eldest grandson, because [Property D] had a larger land area and was newer. This intention was clearly reflected in [M]’s mirror wills. ²⁰³ When Mr Tan took instructions from the Deceased to prepare the 5th Will on 26 November 2020, he was not made aware of [M]’s wills, nor the fact that [M] was certified to have lost mental capacity in August 2020. As a result, although Mr Tan explained to the Deceased that his share in [Property D] would pass to [M] if he predeceased her, Mr Tan did not go further to explicitly state that [Property D] would consequently be subject to [M]’s will, under which [GS1] would inherit the property. ²⁰⁴ In any event, Mr Tan was not given a copy of [M]’s last will and thus, Mr Tan was unaware of its contents. It is also not for Mr Tan to ask for a copy of [M]’s last will or enquire about its contents from the Deceased so that he could further advise or remind the Deceased.

133 Given the above, the 1st Defendant submits that the Deceased had “forgotten” about [M]’s mirror wills and the provision in respect of the two Neighbouring Properties. Even if the Deceased did remember, he was not advised and thus did not appreciate the implications and consequences of swapping the devise of the two Neighbouring Properties. ²⁰⁵

134 The Plaintiff argues that the failure of the devise is an “inadvertent consequence” of complex property law and does not indicate a lack of testamentary capacity. In other words, the Plaintiff’s position is that the Deceased was clear about what he wanted: [GS1] was to be bequeathed [Property L] and the 1st Defendant was to be given [Property D] if [M] predeceased the Deceased. The fact that the 1st Defendant might ultimately receive nothing because of the operation of survivorship and the terms of [M]’s last will is an unfortunate “tragedy of legal drafting”. ²⁰⁶ The Plaintiff relies on the testimony of Prof Kua, emphasising that “forgetting” technical joint tenancy details is a common lay person’s error and does not signify dementia. ²⁰⁷ That would extend in my view to the Deceased “forgetting” to whom (or to which grandson) [M] had bequeathed the Neighbouring Properties in her last will. It also goes without saying that the Deceased would also not know nor be able to predict whether he would predecease [M] at the time he executed his 5th Will. If [M] had predeceased him, then each grandson would receive one of the two Neighbouring Properties. I agree with the Plaintiff that the Deceased’s failure to realise that the swap may lead to the 1st Defendant receiving no property at all in the event that he should instead predecease [M] due to the operation of survivorship and the terms of [M]’s last will, does not indicate a lack of testamentary capacity. But did the Deceased understand and approve the conditional disposition actually contained in the 5th Will, notwithstanding that he might have failed to appreciate how [M]’s separate will could affect his broader objective of leaving one Neighbouring Property to each grandson?

135  The learned editors of Theobald are of the view that the requirement of knowledge and approval is a requirement that the testator understands and approves the actual effect of the will being executed (Theobald at para 4-042). It is not enough to say that the testator merely knew what the words contained in the will said (see, for example, Hoff v Atherton [2004] EWCA Civ 1554 at [64]). Although some judges have stated that proof of a testator’s understanding of the legal effect of the will is not required in all cases, the editors of Theobald submit that this is actually an evidential point recognising that in most cases, where the effect of the will is straightforward and accords with the words of the will, and where no suspicious circumstances arise, the reading over the will and the explanation that the solicitor is expected to have given prior to the execution would create a presumption (or inference) that the testator did understand its actual legal effect (at para 4-042). The court should consider whether the testator knew and adopted the disposition actually expressed in the will and whether, having done so, he was mistaken about its legal or practical consequences. If a provision materially departs from the testator’s instructions and that departure was neither brought to his attention nor knowingly adopted by him, the propounder may fail to establish that the provision expressed the testator’s mind. By contrast, where the testator knew and agreed to the specific words or disposition used in the will, knowledge and approval is not ordinarily undermined merely because he or the draftsman misunderstood or could not have foreseen their legal effect.

136 Applying that distinction, the first question is whether the Deceased understood and adopted the conditional devise of [Property D] actually contained in the 5th Will. Here, the evidence suggests that Mr Tan had informed the Deceased that [Property D] was held in joint tenancy and his share would pass to [M] upon his death before [M]’s. Throughout the will-making process, the Deceased had nodded his head or said “si” or “tio” (in the Teochew dialect) or “okay”, which Mr Tan reasonably took to mean that the Deceased understood and agreed with what he had said. The Deceased’s nods and brief affirmations may not, when viewed alone, be sufficient affirmative proof that he understood the will. Their significance lies in the broader evidence that he had participated in an iterative drafting process, given specific instructions, made amendments to successive drafts and approved a clause which expressly made the gift of [Property D] conditional upon [M] predeceasing him. ²⁰⁸ The express condition demonstrates that the Deceased understood and accepted that the devise to the 1st Defendant would not take effect if [M] survived him. That evidence is sufficient to establish that the Deceased understood and approved the conditional devise of [Property D] to the 1st Defendant.

137 The Deceased might well have overlooked the contents of [M]’s will and failed to consider how the swap would implicate the 1st Defendant’s inheritance in the event that the Deceased should predecease [M]. Had the contents of [M]’s will been brought to his attention, he might have chosen not to swap the Neighbouring Properties around. However, all that is entirely speculative. It remains that the Deceased had decided to swap the Neighbouring Properties because [GS1] had stayed in [Property L] for some years, maintained and renovated it and kept the rental income to support his growing family. Whatever the scope of Mr Tan’s professional obligations, his failure to ascertain the terms of [M]’s will and bring such terms to the Deceased’s attention (which I do not think would be within his scope of work in any case) does not by itself establish that the Deceased failed to understand and approve the provisions of the 5th Will. The fact that the Deceased had likely “forgotten” about the details of the provisions in [M]’s will (as the 1st Defendant submits) ²⁰⁹ is not a ground to invalidate the 5th Will. Ultimately, the Deceased’s failure to account for [M]’s will may mean that the testamentary plan did not achieve his broader objective of leaving one Neighbouring Property to each grandson. It does not necessarily mean that he was unaware of or did not approve the conditional gift contained in the 5th Will. I find on the totality of the evidence that the Deceased knew and approved the conditional gift of [Property D] contained in the 5th Will to the 1st Defendant. As the Deceased had understood what he was doing and its effect, the conditional gift to the 1st Defendant of [Property D] had represented the Deceased’s testamentary intentions.

138 In fact, it is well-established that a mistake or mistaken belief as to facts (not stemming from a delusion or a disorder of the mind) on the part of the testator does not invalidate a will even if it caused him to include particular gifts or provisions in the will (Williams on Wills vol 1 (Francis Barlow et al) (LexisNexis, 11th Ed, 2021) at para 5.6; Theobald at para 4-055, referring to Ball v Ball [2017] EWHC 1750 (Ch) (“Ball v Ball”) at [57]). Ball v Ball concerned a dispute of the will of a testatrix. Her will excluded three of her children, who had reported her husband (ie, their father) for sexual abuse. The question was whether the testatrix was labouring under any significant misapprehension or mistake (particularly, whether she believed in her husband’s innocence when he was in fact guilty) at the time she made her will. The judge found that even if the testatrix had been acting in the mistaken belief that her husband was innocent of the charges against him, when in fact he was guilty, that would not be enough by itself to show that either she was suffering from an insane delusion, or that she did not have sufficient memory for the purposes of making a will (at [57]).

139 Although Ball v Ball concerned the finding of testamentary capacity (as opposed to knowledge and approval), the principle may similarly be applied to the present case. Even if the Deceased had been acting under some mistaken belief or had simply forgotten about certain provisions in [M]’s last will (and in particular, to whom [M] had bequeathed [Property D] in her will), that alone cannot invalidate his 5th Will. The evidence shows that the Deceased understood that his joint share of [Property D] held in joint tenancy with [M] would pass to [M] upon his death. That is sufficient to prove that he had understood and approved this provision and its effect at the time he executed his 5th Will to bequeath [Property D] to the 1st Defendant only if [M] predeceased him.

140 The 1st Defendant takes issue with the way Mr Tan took instructions from and advised the Deceased, citing the following reasons:

(a) Mr Tan did not take contemporaneous attendance notes of his meeting with the Deceased.

(b) Mr Tan wrongly inferred from the Deceased’s nodding that he understood the explanation; instead, Mr Tan should have asked the Deceased to confirm verbally that he fully understood and agreed with what was being conveyed.

(c) Mr Tan did not follow his stated modus operandi (see [129] above). In some instances, he amended a clause even though he had made no handwritten annotation indicating that the amendment had been instructed by the Deceased. In another instance, the amendment in the draft he prepared did not correspond with his annotation. ²¹⁰

141 Separately, the 1st Defendant submits that Mr Tan either misunderstood the Deceased’s instructions on the devise of [Property G] or, if he understood them correctly, failed to give effect to those instructions when preparing the 5th Will. For example, in the 2nd, 3rd and 4th Wills, the Deceased’s intention was always to give [Property G] to the Plaintiff, 2nd Defendant and 3rd Defendant in equal shares. This was also reflected in the Typewritten Note. Mr Tan claims that when this clause was drawn to the Deceased’s attention, he changed his mind and wanted to “put as five persons equally”, which is why Mr Tan wrote “X 5 equal” against Clause 9 of the copy of the 4th Will. However, [Property G] was eventually devised equally to the Plaintiff, 2nd Defendant and 3rd Defendant. Mr Tan himself could not recall why he made the annotation — specifically, whether it referred to “five children” or “five shares”. ²¹¹

142 Crucially, the 1st Defendant says that Mr Tan, being a layman with no formal legal training, had given erroneous advice to the Deceased regarding the effect of his intended will. This caused the Deceased to harbour a misunderstanding of what his will entailed.

143 First, as explained above at [53], Mr Tan advised the Deceased that there would be a “gap” if the No Contest Clause was triggered because there was nothing in the will providing for who was to decide how the forfeited inheritance was to be dealt with. The inheritance forfeited by the dissenting beneficiary would then have “end[ed] up as an intestacy clause”. ²¹² Mr Tan thus proposed addressing this issue by including the Absolute Discretion Proviso, which the Deceased agreed with. ²¹³ According to the 1st Defendant, such advice was in fact erroneous because if the No Contest Clause was triggered, any forfeited inheritance would simply have formed part of the Deceased’s residuary estate. Pursuant to the “Distribution of All Other Assets” clause, the forfeited inheritance would then be divided equally between the Plaintiff, 2nd Defendant and 3rd Defendant. ²¹⁴ However, the inclusion of the Absolute Discretion Proviso has now led to a curious practical consequence: if the Plaintiff were to be the dissenting beneficiary, there would be nothing to prevent him from directing that forfeited inheritance back to himself. The 1st Defendant submits that this would make a mockery of the No Contest Clause and could not have been the Deceased’s intention. ²¹⁵

144 Second, Mr Tan did not independently verify the manner of holding of properties owned by the Deceased. Mr Tan’s testimony was that he asked the Deceased who each property belonged to and accepted the Deceased’s answers at face value. For example, if the Deceased replied that the house belonged to him and his wife, Mr Tan assumed that the property was under a joint tenancy with [M]. ²¹⁶ Apart from the fact that the Deceased himself might not have been able to accurately recall the manner of holding of each property, Mr Tan made erroneous assumptions which caused him to give wrong advice to the Deceased. In the case of [Property G], the Deceased told Mr Tan that it was owned in five equal shares, which Mr Tan expressly reflected as being “held in tenancy-in-common” in the 5th Will. Mr Tan then advised the Deceased that his share of the house would be part of his estate which would pass on to his beneficiaries under his will. The advice was incorrect as [Property G] was held in the names of five owners as follows:

The Deceased’s share thus passed on to [M] under the law of survivorship. Mr Tan conceded during cross-examination that “on hindsight” this part of the 5th Will did not represent the Deceased’s intention and wishes. ²¹⁷ Similarly, Mr Tan wrongly reflected [Property E] as being under a joint tenancy when it was in fact solely owned by the Deceased. ²¹⁸

145 I do not need to determine the correct construction of the No Contest Clause. That question is strictly speaking not before me. I proceed on the basis most favourable to the 1st Defendant that Mr Tan’s advice to the Deceased concerning its legal operation was wrong. Mr Tan may also not have been accurately apprised of the full details of the manner of holding of [Property G] and [Property E] by the Deceased. As such, it may establish or evidence that the Deceased had himself been labouring under his own mistake of fact or under a mistaken belief of the manner of his holding of [Property G] and [Property E] when he made his bequeaths for his 5th Will. However, as stated above at [138], a mistake or mistaken belief as to facts on the part of the testator does not invalidate a will. This is so even if the mistaken belief concerns the legal effect of the provisions (ULV v ULW at [36]; Halsbury’s Laws of Singapore vol 15 (LexisNexis, 2016 Reissue) at para 190.194). Even if the testator objects to certain words being inserted but is persuaded to agree to this by entirely wrong advice as to their effect, the mistake must stand (Theobald at para 4-056, referring to Collins v Elstone [1893] P 1 (“Collins v Elstone”)). A testator cannot be understood to be saying that they approve the words they use if, and only if, the words have the desired meaning (Theobald at para 4-056, referring to Beech v Public Trustee [1923] P 46 at 53).

146 In Collins v Elstone, the testatrix made two wills, the second of which disposed only of a small insurance policy on her life. One of the plaintiffs, Mr Tuffley, acted for her in drafting the second will. At the commencement of the second will were the words: “I hereby revoke all wills by me at any time heretofore made”. The testatrix objected to those words, saying that if they revoked her first will, she would not sign it. However, Mr Tuffley erroneously advised her that because the second will only referred to the insurance money, it would not have the effect of revoking the previous will which dealt with other types of provisions. Acting on that erroneous advice, the testatrix signed the second will as it stood. The court held that the words of revocation could not be struck out despite acknowledging that the second will did not express the real intentions of the testatrix. It is immaterial for present purposes whether Mr Tuffley was legally trained. In any event, although the court described Mr Tuffley as “ignorant… doubly ignorant” as to the effect of the revocation clause, it was silent on whether he was legally qualified. The point is that Collins v Elstone adopted the reasoning in Morrell v Morrell (1882) 7 P D 68, that where the testatrix employed another person to convey her meaning in technical language, and the testatrix decided or agreed to adopt that technical language, the mistake of that person would be treated as the testatrix’s own mistake. It would be as if the testator had used that technical language herself, albeit wrongly or mistakenly. Applying the above principle to the present case, the Deceased’s mistaken belief as to the No Contest Clause (owing to the wrong advice given to him) and his manner of holding of [Property E] and [Property G] cannot invalidate the 5th Will.

147 I turn finally to the “X 5 equal” annotation. In my view, it is more probable than not that the annotation concerned the existing ownership of [Property G], rather than the Deceased’s intended testamentary disposition of that property. Mr Tan’s evidence is that, when taking instructions, he systematically went through the 4th Will with the Deceased, asking him both about the ownership of each property and whether there was to be any change to the intended beneficiary (see [100] above). In that context, the Deceased’s statement that [Property G] was held in five equal shares is explicable. There were five persons named as owners of the property: the Deceased and [M], who together held a 40% interest as joint tenants, and the Plaintiff, 2nd Defendant and 3rd Defendant, who each held a 20% interest as tenants-in-common. The Deceased’s description was therefore not legally precise because he and [M] did not each hold a separate 20% interest. To that extent, the Deceased was labouring under a mistaken understanding of the precise legal manner in which [Property G] was held. Nevertheless, it broadly corresponded with the proportions of ownership if the Deceased treated their aggregate 40% joint interest as notionally divided equally between them. It is therefore plausible that “X 5 equal” simply reflected what the Deceased had told Mr Tan about the existing manner of holding.

148 This interpretation is also more consistent with the documentary evidence. The Deceased’s intended disposition of his interest in [Property G] had remained unchanged. Under the 3rd and 4th Wills, his interest was to be divided equally among the Plaintiff, 2nd Defendant and 3rd Defendant. The same three-way disposition was recorded in the Typewritten Note. No five-way disposition was subsequently incorporated into any draft of the 5th Will or the executed instrument. Nor is there any obvious group of five beneficiaries to whom such a disposition would potentially refer. On balance, I therefore find that the “X 5 equal” annotation more likely recorded the Deceased’s understanding of the existing ownership of [Property G]. It follows that the annotation does not establish that Mr Tan misunderstood or failed to give effect to the Deceased’s testamentary instructions. The final three-way disposition is consistent with the 3rd Will, 4th Will and Typewritten Note, and the evidence is that the final provision was explained to and adopted by the Deceased.

149 Altogether, the Deceased himself demonstrated a clear command of the will-making process on 26 November 2020. ²¹⁹ His conduct showed his active participation and knowledge and approval:

(a) He amended the draft will to appoint the Plaintiff as the sole executor (as opposed to having joint executors). ²²⁰

(b) He directed the addition of the word “surviving” to the clause under the header “Provision of Substitute Beneficiaries”.

(c) He insisted on the inclusion of the No Contest Clause. Mr Tan had to copy the No Contest Clause from the 4th Will for insertion into the 5th Will at the Deceased’s instruction although this was not a “standard clause” in the templates for wills used by SimplyWills Pte Ltd. ²²¹

(d) When Mr Tan advised the Deceased that there would be a “gap” if the No Contest Clause was triggered (because the inheritance forfeited by the dissenting beneficiary “will end up as an intestacy clause” ²²² ), the Deceased accepted Mr Tan’s advice to insert the Absolute Discretion Proviso. ²²³ Regardless of whether the advice given by Mr Tan was legally correct, the Deceased’s response provides an indication that he was mentally engaging with the proposed clause and had considered the advice given before making a deliberate decision to have that clause inserted as advised.

150 Although the preparation of the 5th Will was afflicted by certain mistakes, the affirmative evidence establishes that the Deceased personally gave the dispositive instructions, participated in successive revisions and knowingly adopted and approved the final draft. I therefore find that the Deceased knew and approved of the entire contents of the 5th Will.

151 Where a party seeks to challenge the validity of a will on the basis that the testator was under undue influence, that party bears the burden of proof. In the context of probate proceedings, undue influence means coercion, ie, that the testator is coerced into making a will which he or she does not want to make. The persuasion must have been of such intensity as to overpower the volition of the testator without actually convincing him. The party alleging the undue influence must prove that the party accused of undue influence dominated the testator to such an extent that the testator’s independence was so undermined that the accused party’s domination caused the testator to execute the will (UWF v UWH [2021] 4 SLR 314 (“UWF v UWH”) at [221]–[222]).

152 The 1st Defendant argues that the Deceased was under the undue influence of the Plaintiff when he executed the 5th Will on 26 November 2020. The Deceased was then 92 years old and suffered from severe physical pains (such as sciatica, back pain, joint and feet pain) as well as deteriorating cognitive ability. [M] also frequently displayed violent, abusive and aggressive behaviour towards the Deceased. This made him frail, fragile and vulnerable. ²²⁴ During this period, the Plaintiff brought the Deceased out for hours almost every day and engaged in protracted conversations at night past the Deceased’s bedtime. As evinced by the audio recordings, ²²⁵ some of these conversations involved the Plaintiff guilt-tripping the Deceased, repeating to the Deceased that he was the only one who looked after the Deceased’s interests and speaking ill of his siblings (ie, the 2nd and 3rd Defendants): ²²⁶

(a) On 20 July 2020, the Plaintiff blamed the Deceased for giving cash bequests of over $1.6m each to the 2nd and 3rd Defendants and not giving the same to him. He also blamed the Deceased for not appointing him as a donee in his and [M]’s LPA. He accused the Deceased of “stabbing him in the back” and “playing him out”. He claimed that unlike the 2nd Defendant, he would not control the Deceased and had “great patience” in answering the Deceased’s questions. The Plaintiff also said that the 2nd Defendant only “want[ed] more power” while the 3rd Defendant was “stirring shit” and only “[took] care of his inheritance”. He told the Deceased that the 2nd and 3rd Defendants were “in cahoots with each other” and reminded the Deceased that the 3rd Defendant was adopted. ²²⁷

(b) On 20 August 2020, the Plaintiff repeated that the 2nd and 3rd Defendants were “in cahoots” and “unfilial”. He also emphasised that the 3rd Defendant was adopted, had “bad genes” and intended to “grab” the “family[’s] inheritance”. The Plaintiff further urged the Deceased not to “give” [Property M] to the 3rd Defendant, and to transfer the shares in both [Company C] and [Company B] to the Plaintiff solely. ²²⁸

(c) On 3 November 2020, the Plaintiff again reminded the Deceased that the 3rd Defendant was adopted and had bad genes, and that the 2nd and 3rd Defendants were “in cahoots” and “ganging up” against the Deceased. He also said that the 2nd Defendant was “only interested in the money, not the business”. ²²⁹

153 Moreover, on 26 November 2020 (ie, the day of execution of the 5th Will and the LPA), Mr Tan arrived at the Plaintiff’s residence at “about 1.00 plus” in the afternoon. ²³⁰ The LPA was signed first (with Mr Tan being the translator), followed by the 5th Will. Mr Tan’s car was photographed still parked in the garage of the residence at 10.08pm that day, ²³¹ from which the 1st Defendant infers that the session lasted over eight hours. Mr Tan claimed during cross-examination that the session actually ended around the usual dinner time (ie, 6pm to 7pm) and he “could have” gone out for dinner before retrieving his car after dinner. ²³² The 1st Defendant considers this explanation incredible. The 1st Defendant submits that this is yet another instance of the Plaintiff’s incessant and protracted badgering of a vulnerable 92-year-old man who was in an extremely vulnerable state, culminating in an increase in the Plaintiff’s inheritance by $22m, and a decrease in the 2nd and 3rd Defendants’ inheritance by $6.45m and $15.55m respectively. ²³³

154 The 1st Defendant argues that the undue influence exerted on the Deceased was not just for the making of the 5th Will. Shortly before the execution of the 5th Will, on 20 November 2020, the Deceased withdrew $260,000 from an account jointly held by him and [M]. The money was transferred into a joint account between the Deceased and the Plaintiff. On 25 November 2020, the Deceased withdrew $792,755.07 from another joint account he had with [M] and deposited it into another account jointly held by him and the Plaintiff. ²³⁴ The 1st Defendant claims that the Plaintiff had “prevailed upon and caused his father” to transfer these large sums of money. ²³⁵ The Plaintiff claims that the transfers were made because the Deceased was afraid he could not withdraw the money (because the 2nd Defendant had apparently notified the bank that the Deceased “[could] not withdraw”) and the Deceased wanted to use the money for legal fees. ²³⁶

155 The Plaintiff discredits the audio recordings by alleging spoliation of evidence. He points to the fact that the 1st Defendant had admitted to deleting audio files he unilaterally deemed to be “rubbish” or “irrelevant”. Although the 1st Defendant claims that it was done to “clear space”, ²³⁷ the Plaintiff says that this renders the audio evidence “incurably prejudiced and completely devoid of context”. Moreover, even accepting the audio recordings, the Plaintiff’s conduct merely amounts to “persuasion” which does not cross the threshold for undue influence. ²³⁸

156 In my view, there is no need to determine whether the deletion of other recordings amounts to spoliation of evidence. Even taking the recorded exchanges relied upon by the 1st Defendant at their highest, they establish persistent persuasion but do not prove that the Plaintiff overbore the Deceased’s volition. The timing and amount of the transfers into accounts jointly held by the Deceased and the Plaintiff contribute to the need for careful scrutiny of the Plaintiff’s evidence. The explanation that the moneys were transferred because of concerns about access to the accounts and anticipated legal expenses is not wholly persuasive, particularly given the amounts involved. Nevertheless, the evidence does not establish that the Plaintiff procured the transfers through coercion and domineering conduct overpowering the will of the Deceased or that they formed part of a course of domineering conduct which had undermined the Deceased’s independence to such an extent that it also caused the Deceased to execute the 5th Will.

157 Having assessed the evidence on the whole, my view is that the 1st Defendant has failed to discharge his burden of proving that the Deceased was under the Plaintiff’s undue influence at the time of the execution of the 5th Will. I advance four reasons for this conclusion.

158 First, the evidence demonstrates that the Deceased was not only capable of thinking and acting independently, he was also capable of expressing his opinions and views by himself on the day of the execution of the 5th Will:

(a) Mr Mahtani testified that the Deceased had instructed him in Malay that the Plaintiff was not exercising any pressure or undue influence on him, nor attempting to sour his relationships or sow discord between him and other family members. ²³⁹ The Deceased also directly told Mr Mahtani, of his own accord, that the Plaintiff was not influencing him. ²⁴⁰

(b) Mr Tan’s evidence is that the Deceased was “clearly able to decide on his own at all times and there were no indications otherwise”. ²⁴¹ According to Mr Tan, the Deceased was able to articulate to him what the Deceased wanted to do with his assets and even to insist that the No Contest Clause be added. ²⁴² Mr Tan also testified that it was part of his professional practice to observe the body language of the client and any third parties to ensure there was no undue influence on the client. ²⁴³

159 The photograph adduced by the 1st Defendant establishes only that Mr Tan’s car remained at the premises at 10.08pm. It does not, without more, establish that the Deceased was continuously engaged in the LPA and will-writing processes for more than eight hours or that the Plaintiff was there unduly influencing the Deceased or domineering over him during the whole time on that day.

160 Second, the evidence shows that it was the Deceased himself who sought [N]’s help in finding someone to assist in the preparation of his 5th Will and [N] had recommended a will writer who was fluent in Teochew to prepare the 5th Will (see [119] above). ²⁴⁴ It was therefore [N], and not the Plaintiff, who arranged for Mr Tan to attend before the Deceased. In my view, [N]’s evidence carries considerable weight: he is not a beneficiary under any of the wills, ²⁴⁵ he appears genuinely devoted to the Deceased due to personal gratitude and his evidence is consistent. ²⁴⁶ In fact, it appears that [N] does not have a close relationship with the Plaintiff due to historical work-related disagreements, ²⁴⁷ reducing the likelihood that [N] would lie on oath just to benefit the Plaintiff.

161 Although the Plaintiff helped to draft the Typewritten Note and allowed his place of residence to be used as the location for the preparation and execution of the 5th Will, Mr Tan’s evidence is that he had taken instructions directly from the Deceased, who did not rely heavily on the Typewritten Note. In contrast, the Deceased had made certain decisions that deviated from the changes indicated in the Typewritten Note (see above at [53] and [100]). The 5th Will was thus not an exact reproduction of the changes recorded in the Typewritten Note. Moreover, during the signing of the 5th Will, Mr Tan only noticed [N] in the room (see [101] above). As I accept that it was likely the Deceased himself who initiated the process and [N] who arranged for Mr Tan’s attendance, it is more likely that the execution of the 5th Will was the Deceased’s autonomous decision rather than one procured through the Plaintiff’s coercion.

162 Third, there is insufficient evidence to establish that the Plaintiff had acted to isolate the Deceased from the 1st, 2nd or 3rd Defendants. The 1st Defendant’s case is that the Plaintiff exerted undue influence by isolating the Deceased from the 2nd and 3rd Defendants and actively minimising the interactions they had with the Deceased. Such isolation took the form of (a) the Plaintiff bringing the Deceased to the office every day to stay there for long hours during times when the 2nd Defendant was not in the office; or (b) the Plaintiff and his wife physically remaining in the Deceased’s residence when the 3rd Defendant visited the Deceased and [M]. ²⁴⁸

163 However, the evidence suggests that the Plaintiff had not obstructed the 1st, 2nd or 3rd Defendants from interacting with the Deceased, whether physically or otherwise:

(a) The 1st Defendant conceded that both he and the 2nd Defendant possessed the Deceased’s phone number and either of them could have called the Deceased anytime, and vice versa. The 1st Defendant expressed concern that their discussions with the Deceased were at risk of being scrutinised by the Plaintiff, but the 1st Defendant could not point to any overt act or indication that the Plaintiff had prevented the 1st Defendant or 2nd Defendant from meeting and conversing with the Deceased. ²⁴⁹ In fact, when the 2nd Defendant was able to speak privately to the Deceased in his office on 31 December 2020, it was the 2nd Defendant who chose to discontinue the conversation when the Plaintiff returned. ²⁵⁰ This suggests that any barrier to interaction was driven by the 1st Defendant’s and 2nd Defendant’s desire to avoid the Plaintiff, rather than the Plaintiff taking active steps to isolate the Deceased.

(b) Similarly, it is likely that the Deceased went to the office of his own free will. There is insufficient evidence to reject the Plaintiff’s account that the Deceased was brought to the office only when he expressed a desire to do so. ²⁵¹ It would not be unusual or unexpected for the Deceased to be comfortable staying in the office of the business he had built up from scratch, ²⁵² or that the Deceased would remain attached to the business even after retirement. There may be many other reasons for the Deceased to go to the office. For instance, it might be boring for the Deceased to remain at home every day. Having regard to [M]’s frequent display of violent, abusive and aggressive behaviour towards the Deceased (see [152]), it would not at all be surprising for the Deceased to prefer going to the office than to remain at home. Accordingly, I do not link the bringing of the Deceased to the office by the Plaintiff as the Plaintiff’s attempts at isolating the Deceased from the 1st and/or 2nd Defendants.

(c) It is also not denied that when the Deceased was not in his bedroom, the Plaintiff would ensure that the Deceased’s bedroom was locked. However, the Plaintiff maintains that this was at the Deceased’s request to ensure that no other persons would place visual or audio recording devices in the Deceased’s bedroom. ²⁵³ This was allegedly because the 3rd Defendant had placed an audio recording device in the Deceased’s bedroom to secretly record his conversations. ²⁵⁴ This allegation is supported by Mr Mahtani’s evidence that the Deceased had told Mr Mahtani that the 2nd Defendant and a few family members were spying on the Deceased and the Deceased had found audio devices at home. ²⁵⁵ Viewed in this context, the Plaintiff’s decision to lock the Deceased’s bedroom appears to be in compliance with the Deceased’s own wishes, rather than an instrument of coercive control. Apart from this, it shows the Deceased’s awareness of what was happening and his presence of mind to take the necessary precautions. I also note that the Deceased retained the mental faculties to be able to remember and communicate these incidents to Mr Mahtani.

164 Fourth, an unequal distribution of assets based on a testator’s personal relationship with the beneficiaries is not unusual. Persuasion and influence are not undue influence in the sense of coercion. A parent is entitled to have favourite and least-favoured child(ren) and to dispose of their estate in accordance with their subjective preferences and the kind of relationships with their children (UWF v UWH at [237] and [239]). At the point when the Deceased executed the 5th Will, he was aggrieved by what he perceived to be: (a) the 2nd Defendant’s defiance in preventing him from dealing with and disposing of his own property in her capacity as [M]’s donee; and (b) the Defendants forming a camp that opposed the Deceased. ²⁵⁶ This friction was what led to the breakdown in their relationship that resulted in the Plaintiff getting a far greater distribution of assets under the 5th Will, rather than the undue influence of the Plaintiff.

165 The recordings show that the Plaintiff sought to exploit and reinforce the Deceased’s grievances against the 2nd and 3rd Defendants and to persuade him to confer greater benefits on the Plaintiff. That conduct was self-serving. The evidence does not, however, prove that the Deceased’s volition was overpowered. The Deceased’s grievances had an objective basis in:

(a) the [Property M] dispute with the 2nd Defendant which began prior to the execution of the 5th Will (see [22] and [23(b)] above) and continued even after the execution of the 5th Will. This eventually led to the eviction of the 2nd Defendant and her whole family from [Property C] and the termination of the 2nd Defendant’s part-time employment with [Company B] and [Company C] by the Deceased (see [24] above). These on any account are serious and drastic actions by the Deceased showing the depth of his anger towards the 2nd Defendant;

(b) the 2nd and 3rd Defendants’ open defiance of the Deceased at the meeting at the accounting firm (see [23(a)] above);

(c) the lawyers’ correspondence (see [23(b)]–[23(e)] above); and

(d) the recording devices secretly planted in the Deceased’s bedroom by the Defendants (see [56], [123] and [124(c)] above).

The Deceased had expressed those grievances to persons other than the Plaintiff and initiated the making of a new will. He had given instructions to Mr Tan during the making of his 5th Will, which were not shown to have been dictated by the Plaintiff. It has therefore not been proved by the 1st Defendant that the Plaintiff had overpowered the volition of the Deceased or undermined his independence, thereby causing the Deceased to execute dispositions in his 5th Will, which the Deceased did not wish to make.

166 For the reasons above, I find on the balance of probabilities that the Deceased possessed the requisite testamentary capacity when he executed the 5th Will and that he knew and approved the contents thereof. I also find that the Deceased did not execute the 5th Will under the Plaintiff’s undue influence. Given my findings, it is not necessary for me to address the validity of the previous wills.

167 In the premises, I pronounce in favour of the 5th Will. I order that HCF/CAVP 9/2021 be removed and direct that the Grant of Probate of the 5th Will be granted to the Plaintiff. The counterclaim of the 1st Defendant is consequently dismissed.

168 I will hear the parties on costs if these cannot be agreed.