Cautionary tales in wills and trusts — and the lessons they teach

Estate planning is one of those tasks that's easy to put off. It feels morbid, it feels expensive, and it feels like something you can always get to later. But “later” has a way of never arriving — and when it doesn't, the people you love are left to clean up a mess in public, in court, and at great cost.

The good news is that some of the most spectacular estate-planning failures in history belong to famous, wealthy people who could have afforded the best legal help on the planet. Their stories are instructive precisely because they're so avoidable. If a Supreme Court Chief Justice, a billionaire industrialist, and the Queen of Soul can get this wrong, so can the rest of us — which is exactly why a properly drafted will or trust is worth every penny.

Here are eight cautionary tales, and the lesson each one teaches.

1. Prince: No Will, Six Years, and Tens of Millions in Fees

When Prince died suddenly in April 2016, the music icon left behind an estate eventually valued at $156.4 million — and not a single page of estate planning. No will. No trust. No spouse or children to inherit automatically.

What followed was a six-year legal slog. Because he died “intestate” (the legal term for dying without a will), Minnesota law decided who inherited: his full sister and five half-siblings. The estate's administrator and the IRS then fought bitterly over what everything was worth, with the IRS initially claiming the estate had been undervalued by roughly $80 million and tacking on a multimillion-dollar penalty. Lawyers, consultants, and administrators were paid tens of millions of dollars to untangle it all. Two of the six heirs died before the matter was even resolved.

The lesson: Dying without a will doesn't mean “no plan.” It means the state writes your plan for you — slowly, expensively, and without any regard for what you actually wanted. A lawyer-drafted estate plan would have let Prince direct where his music, money, and legacy went, and would have spared his family years of public conflict.

2. Howard Hughes: A Fortune and a Forgery

Billionaire aviator and industrialist Howard Hughes died in 1975 leaving one of the largest fortunes in America — and no valid will anyone could find. What turned up instead was the infamous “Mormon will,” a handwritten document that purported to leave a chunk of the estate to a gas-station owner who claimed he'd once given Hughes a ride in the desert.

Courts ultimately rejected it as a forgery.

With no legitimate will, Hughes's vast estate was eventually carved up among nearly two dozen cousins after years of litigation, with enormous sums consumed by taxes and legal fees.

The lesson: A vacuum invites chaos. When there's no clear, professionally prepared, properly witnessed document, opportunists, distant relatives, and the courts fill the gap — and the people closest to you have no protection.

3. Aretha Franklin: Handwritten Wills in a Couch Cushion

The Queen of Soul died in 2018, and for months everyone assumed she had left no will at all. Then, in 2019, a niece searching the house found not one but two handwritten documents — one from 2010 locked in a cabinet, and another from 2014 tucked into a spiral notebook wedged under the cushions of her couch.

The 2014 version even used a smiley face inside the letter “A” as part of her signature. Her sons split over which document should control, and the dispute dragged through the courts for years before finally going to a jury trial in 2023. The jury took less than an hour to decide the couch-cushion document was valid — but only after the family had been pulled apart by litigation and the estate had spent years and resources resolving the question.

The lesson: Homemade, handwritten wills create exactly this kind of ambiguity. Which document is the “real” one? Was it really signed? Did she have the capacity and intent? A lawyer ensures there's one clear, properly executed document — and that it's stored somewhere far more reliable than the sofa.

4. Chief Justice Warren Burger: 176 Words of Trouble

Warren Burger served as Chief Justice of the United States Supreme Court for 17 years. You might assume he, of all people, had an airtight estate plan. Instead, days after his wife died in 1994, he typed his own will on his home computer. The entire document ran about 176 words.

It contained typos. More importantly, it failed to give his executors the power to sell real estate — a requirement under Virginia law — and it wasn't set up to be “self-proving,” meaning the witnesses to his signature could be called to testify in court. The popular version of the story claims his DIY will cost his heirs around $450,000 in avoidable estate taxes.

The fuller truth is more nuanced: Burger and his late wife had actually consulted a lawyer for their overall plan, and her will used up her estate tax exemption, so the big tax bill was largely handled. But the drafting errors in his homemade document were real and did create unnecessary court costs and delays — and the episode became a national punchline for years.

The lesson: Even a brilliant legal mind shouldn't draft his own will. Estate planning is a technical specialty with state-specific formalities; one missing clause about executor powers or witnessing can cost your family time, money, and dignity. DIY tools and forms can't anticipate those traps the way an experienced attorney can.

5. Marilyn Monroe: A Stranger Inherited Her Image

Marilyn Monroe actually had a will when she died in 1962. The problem wasn't the absence of a plan — it was how it was structured. She left the bulk of her residuary estate (75%) outright to her beloved acting coach, Lee Strasberg.

Because the gift was outright rather than held in trust, that share — including the rights to her name, image, and likeness — became Strasberg's to do with as he pleased. When he died in 1982, everything passed to his third wife, Anna, a woman Monroe reportedly never met (or met only once). Anna went on to build a lucrative licensing empire around Monroe's image, which was later sold to a branding company for a reported $50 million. A woman who was a stranger to Monroe ended up controlling — and profiting enormously from — one of the most famous faces in history.

The lesson: How you leave assets matters as much as to whom. Had Monroe left her estate in a trust for Strasberg's lifetime, with the remainder passing to people or charities she chose, a stranger would never have inherited her legacy. A lawyer helps you think two steps ahead — to what happens after your first beneficiary is gone.

6. Heath Ledger: An Outdated Will

When actor Heath Ledger died in 2008, his will had been drafted back in 2003 — before his daughter, Matilda, was born in 2005. Because he never updated the document after becoming a father, it left his estate to his parents and sisters and made no provision at all for his own child.

His family ultimately announced that all the money would go to Matilda, so the story has a happy ending. But that outcome depended entirely on the goodwill of his relatives. Legally, his daughter could have been left with nothing simply because Dad never got around to revising an old document.

The lesson: An estate plan is not “set it and forget it.” Marriage, divorce, a new child, a death in the family, a big change in assets — every major life event is a reason to revisit your plan. A relationship with an estate attorney makes those updates routine instead of forgotten.

7. Stieg Larsson: The Partner Who Got Nothing

Stieg Larsson wrote the global blockbuster Millennium trilogy, beginning with The Girl with the Dragon Tattoo. He died of a heart attack in 2004 at age 50 — before the books were published and went on to sell tens of millions of copies. He left no valid will.

Larsson had been with his partner, Eva Gabrielsson, for more than three decades, but the two had never legally married. Under Swedish intestacy law, that meant she had no legal right to inherit anything. His entire estate — and the fortune the books later generated — passed to his father and brother. Gabrielsson was left out entirely, sparking a painful, drawn-out public dispute.

The lesson: The law often doesn't recognize the relationships that matter most to us. Long-term unmarried partners, stepchildren, close friends, and chosen family have no automatic inheritance rights in most places. If you want to provide for someone the law wouldn't, you must say so in a properly drafted document — there is no substitute.

8. Leona Helmsley: $12 Million for the Dog

Hotel magnate Leona Helmsley, famously nicknamed the “Queen of Mean,” died in 2007 and left $12 million in trust to her Maltese dog, a pet named Trouble — while cutting two of her four grandchildren out of her will entirely. Her instructions were eccentric and the document drew immediate challenges. A judge later stepped in and reduced the dog's trust to $2 million, redistributing the rest.

The lesson: You're generally free to leave your money however you like, including to a pet — but unusual wishes invite legal challenges, and a poorly structured plan can be unwound by a court. A lawyer can help you accomplish even unconventional goals (yes, including providing for a pet) in a way that's legally durable and far less likely to be contested or rewritten by a judge.

What These Stories Have in Common

Strip away the celebrity, and the same handful of mistakes appear again and again:

• No plan at all. The state's default rules take over, and they rarely match what you'd have chosen.

• DIY or handwritten documents. Missing formalities, ambiguous language, and questions about validity turn into expensive court fights.

• Outdated plans. A will that ignores a new child, spouse, or major asset can produce results you'd never have intended.

• The wrong structure. Leaving assets outright when a trust was called for can send your legacy somewhere you never imagined.

• Forgotten people. The law won't protect unmarried partners or chosen family unless you explicitly do.

Every one of these failures is preventable. A few hours with a qualified estate planning attorney — and a periodic check-in afterward — would have spared these families years of litigation, millions in fees, and a great deal of public heartbreak.

The Takeaway

You don't need a $150 million fortune to benefit from solid estate planning. You need a clear, valid, up-to-date set of documents that say exactly what you want, drafted by someone who knows the formalities your state requires and can anticipate the problems you can't see coming. That's the difference between a plan that protects your family and a cautionary tale they tell for decades.

If you've been putting it off, let these stories be your nudge. The most expensive estate plan is the one you never made.

This article is for general informational purposes only and is not legal advice. Estate planning laws vary by state and individual circumstances. Consult a licensed estate planning attorney in your jurisdiction for guidance on your specific situation.