Most people want their will to be clear, simple, and free of surprises. But throughout history, some folks have taken a more… creative approach. From poetic last words to shocking surprises for heirs, a few famous wills have left lawyers, judges, and families scratching their heads.
While these stories are entertaining, they also remind us how important it is to have a well-thought-out estate plan that clearly expresses your wishes—and actually works the way you intend.
Here are some of the strangest wills ever written and the lessons they can teach us.
#1 – The Millionaire Who Left Her Fortune to Her Dog
Hotel magnate Leona Helmsley made headlines when she left $12 million to her dog, Trouble, while cutting two of her grandchildren out of her will entirely. After her death, a judge reduced the pup’s inheritance to $2 million, but Trouble still lived quite comfortably for the rest of her days.
The lesson: You can provide for your pets, but there are better ways to do it. In Arizona, for example, you can create a pet trust that names a caretaker, sets aside reasonable funds for your animal’s care, and spells out exactly how those funds should be used. It’s a smart, structured way to make sure your furry friend is cared for—without making national news.
#2 – The Will Written on a Tractor
In 1948, a Canadian farmer named Cecil Harris was pinned under his tractor in a terrible accident. Knowing he might not survive, he carved his will into the fender of the tractor:
“In case I die in this mess, I leave all to the wife.”
The tractor fender was later removed and presented to the court, which accepted it as a valid will.
The lesson: While this story is dramatic, it shows why it’s so important to create your estate plan before a crisis. A properly drafted and signed will ensures that your wishes are clear, valid, and enforceable—without relying on creative carving, napkin notes, or last-minute panic.
#3 – The Lottery Will
A man in New York decided to leave his entire estate to whoever picked the winning numbers in the next state lottery drawing after his death. Unsurprisingly, this idea caused confusion, legal disputes, and chaos for his would-be heirs.
The lesson: It’s fine to include some creativity in your estate plan—but your will needs to be specific, practical, and enforceable. Unclear or impossible instructions often end up costing your loved ones time and money as the courts try to interpret what you meant.
#4 – The Will That Funded a Haunted House
In the early 1900s, Ohio resident John Bowman believed his family would be reincarnated, so he left money in a trust to maintain his mansion and serve dinner every night in case they returned. The “Bowman Estate” funded this eerie ritual for nearly 60 years—until the court finally ended the trust.
The lesson: Even the most heartfelt wishes can go astray without careful legal guidance. Trusts that go on for too long—or have outdated or unrealistic instructions—can waste money or cause confusion for future generations. Regularly reviewing your plan helps ensure it continues to make sense as laws, finances, and family situations change.
#5 – The Mystery Will in the Couch
In 2019, the family of Aretha Franklin discovered not one, but two handwritten wills hidden in her home—one of them tucked inside her couch cushions. Each version said something slightly different, and the resulting court battle among her sons lasted years.
The lesson: If you update your estate plan, make sure you do it formally and keep the signed copies somewhere safe and accessible. Your loved ones shouldn’t have to go treasure hunting through your living room to find your final wishes.
What These Strange Stories Teach Us
While these unusual wills make for entertaining reading, they also highlight what can go wrong when an estate plan is unclear, incomplete, or created without professional guidance.
A good estate plan doesn’t have to be complicated, but it does need to be:
- Valid under state law
- Clear in its instructions
- Accessible to your trusted decision-makers
- Updated as your life and assets change
When you work with an experienced estate planning attorney, you can make sure your plan protects your loved ones, avoids confusion, and reflects your true intentions—without any courtroom drama or tabloid headlines.
Talk with Us
At The Law Offices of Glenn Bishop, PLLC, we help Arizona families create solid, thoughtful estate plans—no hidden notes, no confusion, and no surprises. Whether you’re just getting started or need to update an old will, we’ll guide you through the process so your wishes are clear and your loved ones are protected.
Contact us today to schedule a consultation and start building a plan that makes sense for you and your family.