A Second Will Surfaced After Probate Was Already Filed

The situation

The letter came six weeks after Saskia had filed the probate application, while she was still waiting for the certificate to issue. It was from a lawyer representing Eun-ji, Dirk's sister, and it stated plainly that a more recent will existed, that it had been properly signed and witnessed, and that Eun-ji intended to have it recognized as Dirk's true final will. It closed by noting, without much subtlety, that Eun-ji was prepared to see the matter through the courts for as long as it took, and that she would rather spend money on lawyers than see her brother's actual wishes go unrecognized.

Dirk had died of a sudden heart attack at fifty-four, after more than two decades as a long-haul truck driver, spending weeks at a time away from home on cross-country routes that kept him on the road more than he was in Sioux Lookout. Saskia, a factory technician, had been married to him for eighteen years. They had no children, by choice, and had built a modest but comfortable life around Dirk's driving schedule and Saskia's steadier factory shifts. The will she had filed for probate was the one Dirk had signed early in their marriage, leaving nearly everything to her, an arrangement they had discussed together at the time and that Saskia had never had reason to think had changed.

Dirk and Eun-ji had not spoken in years, the result of a falling-out over their late mother's care that neither sibling had ever really resolved, each blaming the other for decisions made during their mother's final illness. Saskia had known Eun-ji held a grudge, but had no idea Dirk had had any recent contact with her at all, let alone that a new will existed naming her. The document Eun-ji's lawyer described was dated just under three years before Dirk's death, signed, according to the letter, during a stretch when Dirk was working an extended route through the region where Eun-ji lived, a detail that struck Saskia as both plausible and completely unknown to her until that moment.

Eun-ji had built a successful logistics business over the same years her brother spent driving for other people's companies, and she was open, almost pointedly so, about the fact that she could fund a lengthy court fight without it denting her finances the way it would Saskia's. That imbalance, more than the will itself at first, was what worried Saskia most as she sat down with us for the first time.

The complication

Ontario law generally treats a later, validly made will as replacing an earlier one, at least to the extent the two conflict. That rule is not complicated on paper. What made this file complicated was that nothing about the later will could be taken at face value yet. We had never seen it drafted, had no record of the lawyer or document preparer involved, and had no way to confirm, without investigation, that it had been signed and witnessed the way the law requires, that Dirk had been mentally capable when he signed it, or that nothing improper had happened around its signing during a period when he was away from home and, by Saskia's account, drinking more heavily than usual on that particular stretch of driving.

Those are exactly the kinds of questions that turn a two-will estate into a court fight: is the later document genuine and properly executed, was the will-maker capable of understanding what he was signing at the time, and was he free of undue pressure from whoever benefited from the change in his circumstances. Any one of them can be contested on its own, and contesting them properly means expert evidence, examinations of the witnesses who signed the document, and often months or years before a court resolves the question either way.

The complication for Saskia was not that her legal position was weak. It was that testing it properly, either by challenging the later will's validity outright or defending the earlier one on its merits, would cost real money regardless of who was ultimately right on the underlying facts, and Eun-ji had made clear through her lawyer's letter that she viewed that cost as a tool rather than an obstacle to be managed. A protracted validity fight tends to favour whichever side can outlast the other financially, and Saskia's household, built on two modest incomes with no significant savings set aside for litigation, was never going to be able to match a successful business owner dollar for dollar in legal fees over a multi-year court process.

We had to give Saskia an honest picture from the outset: she had real, substantive grounds to question the later will's circumstances, but pursuing those grounds all the way through a contested court process carried a genuine risk of spending a large share of a $420,000 estate on legal fees before either side reached a final answer, win or lose, leaving considerably less for whoever ultimately prevailed.

What we did

1. Requested the full later will and its execution file from Eun-ji's lawyer, including the names of the witnesses, any notes from whoever had prepared it, and the correspondence around its signing, since a genuine, properly executed document looks very different on paper, in its formatting and its supporting file, from one signed in a hurry or improperly witnessed, and we needed the whole file rather than the will alone to judge which this was.
2. Interviewed Saskia in detail about Dirk's state that particular year, documenting what she recalled about his drinking, his mood, his finances, and any contact he might have had with Eun-ji during the months around the will's date, to assess honestly whether a capacity or undue influence argument had real substance behind it, or was closer to suspicion without any proof strong enough to put in front of a judge.
3. Retained an independent document examiner to review the signature on the later will against several known samples of Dirk's signature from around the same period, an early and relatively inexpensive step that could either strengthen or seriously weaken the case before either side committed real money to a full court process that neither of them could easily afford to lose.
4. Calculated a realistic cost range for a contested validity trial, based on comparable estate litigation files we had handled, and set that figure directly against the estate's total value, so the decision facing Saskia was concrete and numeric, a specific dollar range she could weigh against what she stood to gain or lose, rather than an abstract sense of risk she had to take on faith.
5. Opened without-prejudice settlement talks with Eun-ji's lawyer early, before either side had spent heavily preparing for a trial, flagging the genuine questions we had about the later will's circumstances without overstating how far those questions would ultimately go if actually tested in court, since overselling a weak point tends to backfire once the other side sees through it.
6. Negotiated a split of the estate that reflected genuine uncertainty on both sides rather than a full concession to either will, using the document examiner's preliminary findings and the outstanding capacity questions as leverage without needing a court to actually rule on either issue, which would have cost both estates far more than the split itself ultimately did.
7. Documented the settlement as a formal, mutual release covering both wills, so the agreed division could not be reopened later by either side on any new argument, closing off permanently the exact kind of ambiguity that had allowed the second will to surface and complicate the file in the first place, and giving both women a clean, final number to plan around.
8. Notified the probate court of the settlement, withdrawing the original application and replacing it with an amended one reflecting the negotiated division, so that the certificate that eventually issued matched what Saskia and Eun-ji had actually agreed, rather than either of the two competing documents standing alone as if the other had never existed.
9. Kept Saskia informed of legal costs against the settlement value at every stage, so that when the offer on the table changed, she could immediately see what accepting or continuing to negotiate would mean for her net position, rather than weighing an abstract principle against an unclear number that kept shifting with every round of negotiation between the two lawyers.

The outcome

Saskia and Eun-ji settled on a division of the estate roughly along the lines of sixty-five percent to Saskia and thirty-five percent to Eun-ji, translating to about $273,000 for Saskia against $147,000 for Eun-ji, out of a $420,000 estate. That was a real reduction from what the earlier will alone would have given Saskia, which was close to the full amount, and it was not an outcome she would have chosen if the earlier will's validity had simply gone unchallenged.

The document examiner's opinion, while not conclusive enough on its own to guarantee a win at trial, raised genuine and specific questions about the later will's signature that made Eun-ji's side visibly more willing to settle rather than risk a court finding the document invalid outright and awarding her nothing at all. That leverage, built early and relatively cheaply through one modest expert report, did more for Saskia's negotiating position than a year of full litigation likely would have, without exposing either side to the cost of finding out for certain.

Saskia was candid, in our final meeting on the file, that the outcome felt like a loss even though it avoided a far worse one. She had gone into the process believing the earlier will settled the matter beyond question, and came out of it with less than she expected, a direct result of a document she never knew existed and an opponent who could afford to make the litigation process itself part of the pressure rather than just the substance of the dispute. What the settlement did contain was the much larger risk of losing far more than that, in a fight where the other side had made clear from the first letter that money was simply not the constraint for them that it was for her. She has since told other family members, when the story comes up, that the number she settled for still stings a little, but the number she avoided risking is the one she thinks about more.

What you can learn from this