A 92-year-old man wants to sell one of his eleven properties. His wife co-owns it, but she has dementia, and their daughter holds the authority to act for her. The daughter says no. Within weeks, lawyers are writing to lawyers, a business meeting turns sour in front of the accountants, and the old man signs a new will.
On 2 November 2026, the Straits Times reported on the outcome. The decision is YHJ v YHK and others [2026] SGHCF 28, delivered on 14 September 2026 by Senior Judge Chan Seng Onn in the Family Division of the High Court. The names in the judgment are redacted, so we refer to the family by role.
The case deals with three questions that arise whenever a will is challenged. It also shows how a plan that looks sound on paper can fail in a way no one intended.
The Dispute
The father had built a sizeable fortune in the leather and shoe trade and in property investment. By 2020 he owned eleven properties and held interests in a sole proprietorship and four companies. He made five wills over the years, and his wife made matching wills to go with the first three.
His daughter had long been his right hand in the businesses. The judgment describes her as the “hands” to his “brain”. That relationship broke down in the second half of 2020, and the sale of the jointly owned house was the flashpoint. She felt bound to protect her mother’s assets and thought her mother would not have agreed to sell a house full of family memories.
The timeline in the judgment is short and sharp:
- 20 October 2020. At a meeting at an accounting firm, the daughter and her adopted brother objected to the father’s plans for the factory properties. They did so openly, in front of people outside the family. He was angry.
- 7 and 24 November 2020. The daughter’s lawyers wrote to the father and to her brother, the son. They raised concern that the son was exerting undue influence, said the proposed sale was against the mother’s interests, and proposed a mental capacity assessment of the father.
- 26 November 2020. The father signed his fifth will and a lasting power of attorney.
- 15 February 2021. He died, less than three months later.
The fifth will gave the son the shares in the family businesses, with some shares shared among the son and his two siblings. It made him sole executor. After signing it, the father evicted his daughter and her family from one of his houses, ended her part-time employment and made a police report about her presence in the business offices.
The will was challenged by neither the daughter nor the son. It was challenged by a grandson, a child of the father’s eldest daughter. That brings us to the part that reads like a cautionary tale.
The Houses Nobody Planned For
Two neighbouring houses sat at the centre of the grandson’s case. In the earlier wills, the younger grandson was to receive one, and his elder brother the other. The elder brother had lived in the older house for some years, had maintained and renovated it and was collecting rent from it. The father decided to swap the gifts so that the elder brother kept that house.
The swap defeated the plan. The house the younger grandson was now to receive was owned by the father and his wife as joint tenants. In that form of ownership, when one owner dies the survivor takes the whole property. The father’s half could not pass under his will to anyone else. The wife survived him, and her own will, made years earlier and impossible to change after she lost capacity, left that house to the elder grandson.
The result: the elder grandson received both houses and the younger grandson received neither. The judge accepted that the father had probably forgotten the details of his wife’s will, and that had he known, he might not have made the swap. But the court did not treat that as a ground to invalidate the will. A will can fully express what a testator wants and still fail to achieve what he hoped. The son’s side described it in the proceedings as a “tragedy of legal drafting”, and the judge did not dispute that it was unfortunate.
What the Court Decided
The grandson attacked the will on three grounds. Each one has its own test.
Testamentary capacity. A testator must understand the nature of the act and its consequences, know the extent of his property, know who his beneficiaries are and appreciate their claims, and be free from an abnormal state of mind, such as delusions, that distorts his judgment. The father was 92. He had Parkinson’s disease and had experienced episodes of memory loss, hallucinations and delusions.
The court held that age and illness do not defeat capacity by themselves. The question is whether he understood what he was doing when he signed. According to the Straits Times, the doctors who examined him did not find dementia and attributed some of his symptoms to the side effects of his medication. Five witnesses present on the day described him as alert, lucid, coherent and definite in his wishes: his nephew, two lawyers and two staff of the will-writing company. The judge noted that none of them gained anything if the will stood. The nephew, in particular, had a strained relationship with the son, which made it less likely that he would shade his evidence in the son’s favour.
Knowledge and approval. Once capacity is established, the law presumes the testator knew and approved the contents of his will. That presumption falls away where suspicious circumstances surround the will. The judge found such circumstances here. The son, who benefited most, had prepared a typewritten note of the proposed changes, provided the venue and had probably known of the appointment in advance. More than $1 million had moved from accounts the father held with his wife into accounts held with the son. The will writer had no legal training, and the drafting process contained errors and unexplained annotations.
The son therefore had to produce affirmative evidence that his father understood and approved the dispositions. He did. The father had taken part in a drafting process that went through several drafts, given specific instructions, made amendments and approved a clause that made the gift of one of the houses conditional on his wife dying first. The judge drew a distinction that matters in practice: a testator who adopts the words and the disposition in his will does not lose that will because he, or the person drafting it, misjudged its legal effect.
Undue influence. The standard here is coercion. The influence must be so strong that it overpowers the testator’s will without persuading him. The grandson produced audio recordings in which the son repeatedly told his father that his siblings were “in cahoots”, questioned the adopted brother’s background and pressed him to give the family businesses to the son alone. The judge called this conduct self-serving.
It still fell short. The father’s anger had an objective basis in the house dispute, the open defiance at the meeting and the lawyers’ letters. A parent is entitled to have favourites and to leave an estate according to his own preferences. The court found that the son had reinforced his father’s grievances. It did not find that he had created them or overridden his father’s judgment.
The judge pronounced in favour of the fifth will, directed that probate be granted to the son and dismissed the grandson’s counterclaim. Costs are to be argued if the parties cannot agree.
The No Contest Clause
The second to fifth wills each carried a no contest clause. A beneficiary who disputes the will receives $10,000 and forfeits the rest. The judge did not need to decide how the clause operates and expressly left that question open. The Straits Times notes that it remains to be seen whether the executor will rely on it against the grandson.
We wrote recently about how other legal systems treat these clauses in The Global Jury on No-Contest Clauses. Here, the will writer advised that the clause would leave a “gap”, and a discretion was added to fill it. The grandson argued that this advice was wrong, and that the discretion would let the son, if he were ever the dissenting beneficiary, direct the forfeited inheritance back to himself. The court assumed the advice was wrong and still upheld the will.
Five Lessons
1. Use a lawyer for a will with real assets. The father had two lawyers in the room on the day he signed his lasting power of attorney. He did not ask either of them to prepare his will. The Straits Times reports that he haggled over the will writer’s fee. A will writer takes instructions and records them. A lawyer asks the questions the client does not know to ask, such as how each property is held, what the spouse’s will says and what happens if the order of deaths is reversed. The judge did not think that checking the wife’s will fell within the will writer’s scope of work. That is the gap a lawyer fills.
2. Check how every asset is held. Joint tenancy decides who receives a property on death, whatever a will says. If a property is held jointly in name only, because one spouse paid for it all, the will can say so, and the beneficiaries may then have a basis to ask the court for relief. The Straits Times suggests that a clear statement along those lines might have saved the younger grandson’s gift.
3. Align spouses’ wills. The father and his wife had made mirror wills. When she lost capacity in August 2020, her will was fixed. His later changes ran into a document he could no longer coordinate with. Couples should review their wills together and again after any change.
4. Capacity is a snapshot, so document it. Do not assume age or a diagnosis will undo a will, and do not assume it will not. Where the testator is elderly or unwell, arrange a contemporaneous medical assessment, use independent witnesses, and keep notes. Here the independent witnesses did the heavy lifting.
5. Keep the beneficiary out of the process. The court found the son’s involvement in the preparations raised a substantial suspicion. He survived the challenge, but only after a suit begun in 2021 and a judgment in September 2026. A beneficiary who arranges the venue, drafts notes or pays the will writer invites exactly that scrutiny.
A word on the lawyers’ letters. The Straits Times suggests it is never wise to send legal letters to the head of a family. We would put it more carefully. The daughter’s concerns about her mother’s assets and her father’s circumstances were not frivolous. But letters from lawyers harden positions. Where a family can still talk, a conversation or mediation should come first.
Closing Thoughts
Families tend to ask whether a will is valid. The more useful question is whether it will do what the maker wants. Here the will stood and the plan failed. A 92-year-old with Parkinson’s disease was held to have made a valid will, his daughter lost her place in the family businesses, and one grandson lost a house through a drafting gap that a conversation with a lawyer might have caught.
If you are planning your estate, or have concerns about a will, we are happy to talk it through. Contact Us.
