Estate planning can bring out the sentimental, the generous, and—on occasion—the downright strange. While most people leave their assets to family, friends, or charities, history has seen some truly bizarre bequests that make even the most seasoned estate planning attorney raise an eyebrow.
From haunted heirlooms to pampered pets, these unusual wills remind us that final wishes, no matter how odd, still carry serious legal implications.
Famous (and Strange) Real-Life Unusual Wills
These real-life examples show just how creative—and sometimes eccentric—people can be when deciding what happens to their money, possessions, and even pets after they’re gone.
A Million-Dollar Dog
When hotel heiress Leona Helmsley passed away, she famously left $12 million to her Maltese dog, Trouble.
Although a court later reduced the amount, the gesture highlighted how pet trusts have become a valid and enforceable part of estate planning.
What the Law Says
In most states, including Missouri, you can legally create a trust for the care of your pets. The funds are managed by a trustee who ensures your furry friend is cared for according to your wishes.
However, courts may step in if the amount left seems excessive compared to the pet’s actual needs.
The “Cursed” Doll and the Warning Clause
Over the years, stories have circulated about wills that include eerie warnings or so-called “curses” tied to family heirlooms.
One often-told example involves a haunted doll said to bring misfortune to anyone who tried to sell or discard it—a dramatic reminder that even superstition can find its way into estate planning.
What the Law Says
While a curse has no legal standing, the will itself can dictate what happens to the property.
If an heir accepts the inheritance, they must also accept any conditions or restrictions attached. So, cursed or not, the doll might be legally bound to the heir.
A “Ghost” Clause
Legendary illusionist Harry Houdini took his fascination with the afterlife to the grave—literally. In his will, he asked his wife, Bess, to hold an annual séance every Halloween to try to contact his spirit from beyond. Though Bess honored the tradition for ten years, Houdini never appeared.
What the Law Says
While personal or spiritual requests like Houdini’s are perfectly legal to include in a will, they’re symbolic rather than enforceable. Courts won’t compel an heir to perform a ritual or ceremony, but such instructions still demonstrate how wills can capture the deeply personal beliefs and wishes of the person who wrote them.
Paying It Forward—Forever
In 1926, Charles Vance Millar, a wealthy Toronto lawyer known for his sense of humor, left behind one of the most unusual wills in history. Among his eccentric bequests, he instructed that the residue of his estate be held in trust for ten years, after which it would be given to the Toronto woman who bore the most children during that period.
When the decade was up, the city saw a fierce legal and moral debate—eventually dubbed the Great Stork Derby. After years of litigation, four women who had each given birth to nine children were awarded the estate’s proceeds, which had grown significantly in value due to interest and investment growth.
What the Law Says
Millar’s will is a classic example of a charitable and conditional trust, illustrating how the law can uphold unusual wishes as long as they meet basic requirements of clarity, legality, and public policy.
By contrast, most private trusts are limited by the rule against perpetuities, which prevents individuals from controlling property indefinitely after death.
Why These Wills Matter
Odd or not, these stories illustrate an important point: a legally valid will must be clear, intentional, and enforceable.
Even the strangest wishes can hold up in court—if they’re properly written and witnessed.
The legal system doesn’t judge your reasons; it just ensures your intentions are honored within the boundaries of the law.
That’s why estate planning isn’t just about filling in forms—it’s about crafting a document that carries real legal weight.
Lessons from the Weird and Wonderful
Even though you might not plan to leave your fortune to a ghost or a cat, these unusual cases show the importance of:
- Clarity: Ambiguous instructions can cause confusion or legal disputes.
- Proper Execution: Wills must meet strict legal requirements to be valid.
- Professional Guidance: An experienced estate planning attorney can ensure your wishes—traditional or unusual—are carried out exactly as intended.
- Updating Regularly: Life changes, and so should your will.
So… Can You Leave Your Money to a Doll?
Technically, no—but you can leave it to a person or trust responsible for caring for that doll (or any treasured possession). The law requires a human or legal entity to oversee how your assets are managed.
This is where a comprehensive estate plan becomes invaluable. By working with an attorney, you can structure your plan so your unusual requests—sentimental or symbolic—are respected without creating legal headaches for your loved ones.
Protecting Your Legacy (No Curses Required)
At Ozarks Legacy Law, we’ve seen it all—from straightforward family wills to unique, personalized estate plans that reflect what truly matters most to each client.
Whether your priorities are practical, emotional, or a little unconventional, our attorneys ensure every detail is handled with care and precision.
With over 50 years of combined experience, we make estate planning simple, fast, and tailored to you—usually completed in just two meetings within 7–10 days.
Ready to put your wishes in writing—minus the haunted doll?
Contact Ozarks Legacy Law today to schedule your FREE Planning Session and protect your legacy your way.
