Keeping a Construction Fortune Out of a Public Probate File

The situation

What worried Winston was not dying. At sixty-eight, running a construction company he had built from a two-truck operation into one of the larger firms bidding on projects across the region, alongside his longtime business partner Mathan, who owned the other half of the company, he was blunt about that. What worried him was the idea of his estate becoming a public document, sitting on file at the courthouse for any competitor, subcontractor, or curious former employee to look up once probate opened. He had spent thirty years keeping his company's finances private, and he did not want a decade of careful discretion undone by a probate filing anyone could request.

He came to us specifically asking about an alter ego trust, a structure he had read about that lets someone over sixty-five move assets into a trust during their lifetime, remain the sole beneficiary of the income while alive, and keep those assets out of the probate process entirely when they die, since the trust, not the estate, already owns them. His estate was substantial, somewhere between two and a half and six million dollars once his investment portfolio, the company's value, and a few properties were accounted for, and the appeal of keeping most of that out of a public file was obvious to him.

Winston also named his caregiver, Joost, in his will, a provision that had been in place for several years, made when Winston's health first became a concern and Joost began helping manage his day-to-day affairs. Winston described the relationship as straightforward: Joost helped him, he was grateful, and the bequest reflected that gratitude, nothing more complicated than it sounded.

He brought in a folder of investment statements to get the trust started, expecting the work to be mostly administrative, transferring the accounts and updating the paperwork. What our review of those statements found did not match the account Winston had given us of his own holdings, and it took several conversations, and a fair amount of Winston's patience, before the discrepancy made sense to anyone, including him.

What the review found

An alter ego trust only works cleanly if the assets going into it are actually owned the way the settlor believes they are owned. Winston told us his investment portfolio, roughly two million dollars across several accounts, was held entirely in his own name, straightforward assets he could move into the trust without complication. His statements told a different story. A meaningful portion of one account, opened years earlier, was held jointly with Joost, not solely by Winston, a detail Winston either did not remember or had never fully registered.

Joint ownership changes everything about how an asset behaves on death, but not as simply as Winston assumed. Legal title to an asset held jointly with a right of survivorship does pass automatically to the surviving joint owner, without going through the estate. Whether the survivor actually gets to keep it is a separate question. Where the other joint owner is not a spouse, Ontario law presumes the account is held on a resulting trust for the estate unless there is clear evidence the original owner meant it as a gift, and a caregiver added to an account 'to help with paying some bills' is close to the textbook fact pattern where that presumption applies rather than being rebutted. If that account had simply been moved into an alter ego trust on the assumption it was solely Winston's, the transfer itself would have been legally questionable, since Winston did not have unilateral authority to move an asset he did not solely own, and it risked triggering a dispute with Joost, or later with the estate's other beneficiaries, over who actually owned the money in the account and on what terms.

When we raised the joint account with Winston directly, his account of how it came to be jointly held did not stay consistent. He first said he had no memory of adding Joost to it. When shown the account opening documents, dated to roughly the same period the will provision naming Joost was drafted, he then recalled adding Joost 'to help with paying some bills' during a period when Winston's own mobility was limited, but was vague on whether he had understood, at the time, that joint ownership meant the account could pass to Joost outside the estate, on top of the separate bequest already in the will, or on whether he had ever turned his mind to making Joost an outright gift of the funds rather than simply adding a helping hand to the account.

The gap between what Winston believed about his own holdings and what the paperwork actually showed was not evidence of anything improper on Joost's part. It was, more plainly, evidence that Winston had lost track of a decision he made years earlier under different circumstances, and that decision, left uncorrected, would have interacted with his estate plan in a way he had not intended and, once it was explained to him, did not actually want.

What we did

1. Cross-checked every account against title documents rather than relying on Winston's description of his own holdings, requesting statements and account agreements directly from each institution, which is what surfaced the jointly held investment account and confirmed the ownership structure of everything else going into the trust before any transfer was initiated.
2. Raised the joint account discrepancy with Winston directly, walking him through the account opening records and asking him to explain the history, which took more than one conversation given the inconsistency in his initial recollection, but was necessary before any transfer could proceed accurately or safely.
3. Explained the legal effect of joint ownership, including its limits, in plain terms: that legal title would pass to Joost outside the estate on Winston's death, but that because Joost was not Winston's spouse, Ontario law presumes an account like this is held in trust for the estate unless Winston's donative intent is clearly documented, meaning that without more, Joost's real entitlement to the funds could actually be challenged by the other beneficiaries after Winston's death, not simply added on top of the will's existing bequest as Winston had assumed.
4. Confirmed Winston's actual intentions once he understood the full picture, establishing through direct questions that he did in fact want Joost to keep the joint account as an outright gift, not merely as a convenience arrangement, and that he wanted Joost's total benefit under his estate plan to reflect one deliberate figure, not an accidental combination of a joint account and a separate bequest that happened to overlap without either document accounting for the other.
5. Restructured the plan to match those intentions, adjusting the will's bequest to Joost to account for the joint account Joost would already receive, so the combined total matched what Winston actually wanted to leave rather than an unplanned sum produced by two documents that had never been reconciled against each other.
6. Reviewed the company's shareholder arrangements alongside the trust work, including the buy-sell agreement Winston held with Mathan, his co-owner, confirming how Winston's shares would transition on his death and making sure that structure worked consistently with the alter ego trust rather than creating a separate, unaddressed probate exposure for the business itself, or an unwelcome surprise for Mathan about who he would suddenly be in business with.
7. Transferred the correctly identified solely owned assets into the alter ego trust, including the bulk of the investment portfolio and several properties held in Winston's name alone, structured so Winston remained the sole income beneficiary during his lifetime with full control over the trust's investments and no change to how he managed his day-to-day finances.
8. Had Winston sign a written declaration of gift for the joint account, confirming in his own words, while he had full capacity to do so, that he intended the funds to belong to Joost outright and had not simply added Joost for administrative convenience. This was the step that actually mattered for Joost's protection, since a clear, contemporaneous statement of donative intent is what displaces Ontario's presumption of resulting trust, and without it Joost's claim to the account would have remained open to challenge no matter what Winston privately meant.

The outcome

The alter ego trust was completed with the correctly identified assets, moving the bulk of Winston's investment portfolio and several properties out of his personal estate and into a structure that will avoid probate on those assets when he dies. The company itself, held through a separate corporate structure, was addressed alongside the trust work to make sure share transitions on Winston's death would be handled through the existing shareholder arrangements rather than sitting exposed in a probate file for competitors to review.

The joint account discrepancy, caught before any transfer was made, avoided a real problem rather than creating one after the fact. Had the account been moved into the trust on the mistaken assumption it was solely Winston's, the transfer could have been challenged by Joost, or by other beneficiaries once the estate opened, as an improper dealing with an asset Winston did not fully own. Left unaddressed in the other direction, the account also carried its own risk: without a documented declaration of gift, the other beneficiaries could have argued after Winston's death that the account was never meant as a gift at all and belonged to the estate under the presumption of resulting trust, leaving Joost to fight for money Winston had genuinely intended him to keep. Instead, the account was left exactly as it was, its ownership put beyond doubt by Winston's signed declaration, and the will was adjusted so Joost's total benefit reflected what Winston actually intended rather than an accidental double allocation that nobody had planned for.

Winston got the outcome he originally wanted, an estate substantially shielded from the public probate process, but the path there was not the simple administrative transfer he expected when he first walked in with his folder of statements. What made the difference was checking the paperwork against the story rather than accepting the story on its own, a step that cost Winston an uncomfortable conversation about an account he had genuinely forgotten adding someone to, and saved his estate from a dispute that would only have surfaced once he was no longer there to explain it himself.

Winston later told us he was glad the review had been thorough rather than quick, since the version of the plan he almost signed off on would have left Joost with an unintended windfall and left his other beneficiaries with a smaller share than he actually wanted them to have. The correction cost him little beyond time and one difficult conversation, against a mistake that would otherwise have surfaced only after he was gone.

What you can learn from this