When a Manhattan family discovers a handwritten note tucked inside a deceased parent’s desk, asking that a specific piece of heirloom jewelry go to a favored niece, the next nine months usually belong to Surrogate’s Court. The family naturally expects the informal note to be honored. The law generally does not.
This disconnect between what a person intended and what they legally formalized is the single greatest threat to generational wealth transfer. It is a failure of legal architecture—and it is the exact vulnerability that fractured the estate of one of the most famous women in the world.
Princess Diana passed away in 1997, leaving behind a highly scrutinized estate valued at over £21 million and a formal will. Alongside her legally binding documents, she left a “Letter of Wishes.” This separate, informal document explicitly asked her executors to distribute her personal effects—including highly valuable jewelry and sentimental items—to her godchildren. To a layperson, writing a side letter seems like a deliberate, private way to handle personal property without crowding the main will. But a letter of wishes lacks the enforcement power of a formal testamentary directive. Because the letter was not legally binding, her executors—her mother and sister—successfully petitioned the courts to vary the terms of the estate. The godchildren did not receive what Diana intended. They received a fraction of it, years later, only after the executors had their way.
The Strict Reality of Testamentary Formalities
Stewardship. It demands more than good intentions—it requires enforceable directives. When we evaluate estate plans for high-net-worth individuals, we constantly look for precatory language: words that express a hope or a wish rather than a binding legal command. Relying on the honor system to distribute your wealth is a profound risk.
Under New York law, informal side letters are notoriously dangerous. New York Estates, Powers and Trusts Law (EPTL) § 3-2.1 outlines strict formalities for the execution of a will. For a document to direct the distribution of assets after death, it must be signed at the end by the testator in the presence of at least two attesting witnesses, with specific declarations made at the time of signing. A casual letter of wishes fails this test entirely.
While some jurisdictions are highly lenient about incorporating outside documents by reference, New York is exceptionally strict. If your wishes for your personal property are not executed with full testamentary formalities, your executors are under no legal obligation to follow them. They can simply choose another path, substituting their own judgment for yours.
The Danger of Discretionary Trust Timelines
Diana’s will also established a trust for Prince William and Prince Harry. Her original document stipulated that the princes would receive their full inheritance at age 25. Once again, her executors intervened. They used the legal system to delay the age of outright distribution to 30.
This highlights a fundamental tension in estate planning: the balance between protecting young beneficiaries and respecting the deliberate timeline established by the grantor. When we draft trusts for executives and business owners, we spend significant time discussing the exact milestones for distribution. If you determine that your children should receive funds at age 25, your trust must be drafted so tightly that a trustee cannot unilaterally decide that 30 is a better age.
There are certainly valid reasons to delay a distribution—such as a beneficiary developing a substance abuse issue or facing a severe creditor threat. A well-drafted trust includes contingency provisions for these exact scenarios. But granting a trustee broad, unchecked discretion to delay mandatory distributions simply because they disagree with your timeline invites the exact kind of legal maneuvering that delayed the royal inheritance. We structure these documents so that your timeline is a mandate, not a suggestion.
The Fiduciary Trap
Fiduciary duty means carrying out the intent of the creator. When you select an executor or a trustee, you are appointing a custodian of your legacy. Diana chose close family members, and that choice ultimately backfired.
We frequently advise clients on the realities of fiduciary selection. Family members inevitably bring their own emotional baggage, personal biases, and financial opinions into the administration of an estate. They are far more likely to attempt to alter your plans than an independent professional fiduciary would be. The individuals you appoint must possess the fortitude to execute your exact instructions, especially when those instructions are unpopular with the remaining family.
Securing Your Own Intentions
The failure of Diana’s letter of wishes and the post-death alteration of her trust timelines were not failures of the law. They were failures of execution. If you have specific items—whether a fine art collection, family heirlooms, or closely held business shares—that you want distributed to specific people, those directives must be explicitly written into your will or your revocable living trust.
Good intentions do not survive Surrogate’s Court. Only ironclad legal directives do. If you have written informal side letters to your family, or if you are relying on verbal understandings about how your assets will be handled, your estate is vulnerable. Schedule a 30-minute review of your existing will and trust documents with our office to ensure your actual wishes carry the full weight of New York law.
