← The Probate Archive
— How it went wrong · 33 cases
Strange conditions
Testamentary freedom means you are allowed to be strange about it. Courts enforce conditions right up to the point where they become illegal, impossible, or contrary to public policy — and almost none of the cases here failed because of the condition. They failed because of the drafting.
— The Florida law this runs into
Rule against perpetuities — 90 years, or 1,000 years for trusts created on or after July 1, 2022.
A trust purpose must be lawful, not contrary to public policy, and possible to achieve.
Cy pres — redirecting a charitable purpose that has become impossible or impractical.
Judicial modification when unanticipated circumstances defeat a material purpose.
— Where it happened
The dog that got $12 million· 8-min readFlorida
Leona Helmsley
She left two grandchildren nothing and a Maltese named Trouble twelve million dollars. A Manhattan judge cut the dog to $2M and gave the grandchildren $6M. Then Trouble retired to a hotel in Sarasota with a security detail.
The Great Stork Derby· 8-min read
Charles Vance Millar
A Toronto lawyer with no family left his fortune to whichever woman in the city gave birth to the most children in the ten years after his death. He meant it as a joke about human greed. Then the Depression arrived and it stopped being funny.
The will that created the prizes· 8-min read
Alfred Nobel
Nobel wrote his own will in four handwritten pages, left 94% of his fortune to an organisation that did not exist, and named no country as his home. It took five years, a family lawsuit, and an executor moving securities out of France to make it work.
The name he could not leave to anyone· 8-min read
Babe Ruth
He died in 1948 having built the most valuable name in American sport. Forty-two years later his two daughters sued a publisher for using his photograph and lost outright — New York gave the dead no right of publicity at all. In 2024 one of his shirts sold for $24.12 million.
Poor little rich girl· 9-min read
Barbara Hutton
She inherited a Woolworth fortune at twelve, took control of it outright at twenty-one, and married seven times. Almost nothing about her spending was illegal or even unusual for her class. What is instructive is the structure: a trust that protected her until her twenty-first birthday and then simply stopped.
The gift with three keys· 8-min readFlorida
Bebe Rebozo
Richard Nixon's closest friend left roughly 65% of his estate — about $19 million — to the Nixon Library, on the condition that the spending be approved by Nixon's two daughters and one other friend. The money sat for four years while the approvers disagreed, and a Miami judge finally ordered them into a room together.
The two-hundred-year experiment· 8-min read
Benjamin Franklin
Franklin left £1,000 each to Boston and Philadelphia with instructions to lend it to young tradesmen at 5% and let it compound for two centuries. The cities did roughly that. The money came out in 1990, and Boston still had to litigate who got it.
A membership, a policy, and a trust· 9-min readFlorida
Cryonics contracts
Cryonics is not a bequest and it is not a burial. It is a contract signed while you are alive, funded by a life insurance policy that names the organisation as beneficiary, with the long-term costs held in a separate trust. The legal problems are all in the paperwork.
As near as possible· 10-min readFlorida
Cy pres
You leave money to a charity that no longer exists, or on a condition nobody can meet. The gift does not simply evaporate — a court can redirect it to the nearest charitable purpose you would have wanted. Florida codified that power in §736.0413, and its courts have used it on a wildlife society that never existed and on Janet Reno's homestead.
The paintings the artist gave away· 10-min read
Donor intent
Norman Rockwell gave two paintings to the museum in the town where he had lived. Forty years after his death the museum announced it would sell them to fund its own survival. His sons sued and were told they had no right to be in the room.
The gift with a life estate reserved· 8-min read
Franklin D. Roosevelt
He gave his house to the United States and kept the right to live in it. He gave away his own papers and had to invent an institution to receive them. He died on April 12, 1945; seven months later his family gave up their rights early, and the government moved in.
Burn everything, unread· 10-min read
Franz Kafka's papers
Kafka left written instructions that his friend Max Brod destroy every manuscript, diary and letter without reading them. Brod published all of it. Ninety-two years later the Supreme Court of Israel decided who owned the pile — and the question underneath is one Florida answers every week.
The countess who never existed· 8-min readFlorida
Gunther the German Shepherd
For thirty years a line of German Shepherds has been reported as the richest dog on earth, heir to a German countess. Reporters checked. There is no countess. There never was. The dog does, however, own a mansion on Brickell Avenue — which is a different and more interesting fact.
The $3 million cannon· 8-min read
Hunter S. Thompson
He designed it in 1978, on camera, twenty-seven years before he needed it: a 153-foot tower in the shape of a two-thumbed fist, with a cannon on top to fire his ashes over Colorado. It happened exactly as drawn. It cost a reported $3 million, and his estate did not pay a cent of it.
Control, deliberately· 8-min read
J.D. Salinger
Salinger published nothing after 1965 and sued the people who tried to publish him anyway. He wrote for another forty-five years regardless. The copyrights went into a trust before he died, and the trustees have spent sixteen years doing what he did — saying no, on his behalf, with legal authority to keep saying it.
The will that sold the team· 9-min read
Jack Kent Cooke
He left the Washington football club and its brand-new stadium to his own charitable foundation, with instructions to sell. Two years later the franchise went to a 34-year-old outsider for $800 million — then the most expensive transaction in sports. The widow he cut out of the will sued and reportedly took $20 million.
The oldest instruction still being followed· 8-min read
Jeremy Bentham
His will directed that his body be dissected in front of an audience, then dressed, seated in his own chair with his own walking stick, and kept in a case. It was done in 1832. It is still being done. No court has ever been asked to enforce it.
For as long as she does not remarry· 9-min read
John Jacob Astor IV
The richest man on the Titanic left a pregnant teenage widow the income from a five-million-dollar trust and the use of two great houses — on one condition. She remarried four years later and gave all of it up. The terms are constantly misreported, and the law behind them surprises people.
The house kept ready· 7-min read
John Porter Bowman
Bowman buried a wife and two daughters, built them a $75,000 mausoleum, then left $50,000 in trust to keep his Vermont mansion maintained exactly as he left it — in case the family came back. The money ran out in the 1950s.
The cat who cannot own a bank account· 8-min readStill open
Karl Lagerfeld
He told interviewers his Birman cat was an heiress. French law says an animal is property, and property cannot inherit. Seven years after his death the estate is still tangled with the French tax authorities, and the woman caring for Choupette says nobody has been paid anything.
An estate made of copyright· 9-min read
L. Ron Hubbard
Hubbard signed a new will the day before he died in 1986. About $25 million of a roughly $26 million estate was intellectual property, and the plan routed it through a family trust into religious corporations — one of which the government would not recognise as tax-exempt until 1993.
The house nobody would take· 9-min readFlorida
Marjorie Merriweather Post
She left Mar-a-Lago to the United States as a winter White House, Hillwood to the Smithsonian, and Camp Topridge to New York State. All three institutions handed the gifts back. The richest woman in America could not give her houses away.
The will that made a statute· 9-min read
Peter Thellusson
Thellusson died in 1797 directing his fortune to accumulate through the lives of every son and grandson living at his death. Projections ran to £14 million. Parliament passed a law to stop anyone doing it again, and by the time the last heir was identified in 1859 the costs had eaten the growth.
The will that stopped in 2004· 8-min read
Philip Seymour Hoffman
He signed a will when he had one child and never touched it again. Two more children arrived. He declined the trusts his accountant recommended, and he never married the mother of all three — which left the Internal Revenue Service a very clean shot at roughly $35 million.
Who owns the words· 8-min read
Roald Dahl
Dahl died in 1990 and left a body of work that behaves like a corporation. His family put the rights into a company, apologised in 2020 for things he had said, sold the company to Netflix in 2021, and in 2023 the publisher changed hundreds of words in the books. Every step of that was legal. None of it was his decision.
The word nobody defined· 9-min read
Robin Williams
He did everything right: a funded trust, a prenuptial agreement, two homes carefully allocated. Then his widow and his three children spent a year in a San Francisco courtroom arguing over what the word “memorabilia” means, across a list of roughly 1,200 objects.
Buried in the Ferrari· 7-min read
Sandra West
West directed that she be buried in a lace nightgown, seated in her powder-blue 1964 Ferrari, with the seat slanted comfortably. A Los Angeles court held the instruction unusual but not illegal. San Antonio poured two truckloads of concrete over the grave.
Marry within seven years, or Israel gets it· 9-min read
Shapira v. Union National Bank
An Ohio physician left each son a third of his estate on one condition: marry a Jewish woman with two Jewish parents, within seven years of his death. Otherwise the share went to the State of Israel. In 1974 a probate judge said the condition was perfectly good law.
The womanless library· 7-min read
T.M. Zink
An Iowa lawyer left five dollars to his daughter and the rest of his estate to sit for 75 years, then build a library that no woman could enter and no woman's work could sit on the shelves. His daughter had the will set aside inside five months.
Every painting where he left it· 10-min read
The Barnes Foundation
Albert Barnes wrote a 1922 indenture fixing his collection in place forever: no loans, no touring shows, no colour reproductions, no rearranging a single wall. He died in 1951. In December 2004 a Pennsylvania judge let the whole collection move to Philadelphia — and it is still the most argued-about donor-intent decision in America.
Thirty envelopes in a safe· 9-min read
The sealed royal wills
In England a proved will is a public document anyone can buy a copy of. Except for one family. Since 1910 the wills of senior royals have been sealed by court order, and in 2021 a judge sealed Prince Philip's for ninety years after a hearing nobody was told about.
Seven hundred bank accounts, and other things that were not true· 9-min read
W.C. Fields
The story is that he hid a fortune in hundreds of accounts under invented names. A biographer went and looked: about two dozen accounts, all in his own name. The parts of this estate that were real — a college for orphans, and a body nobody would cremate — took sixteen years to resolve.
The ninety-two year wait· 7-min read
Wellington R. Burt
A Saginaw lumber baron died in 1919 having decided his children would get almost nothing. His will locked the fortune until twenty-one years after the death of his last grandchild alive when he died. Twelve descendants finally collected in 2011.
— The other ways it goes wrong
Died without a willHandwritten willsCapacity & undue influenceTrustee & fee warsPetsRemains & final wishesBlended familiesTaxes & timing
Every case on this page is somebody else's. If any of it sounds like your situation, the fix is almost always cheaper and duller than the case was.
These are not our cases. Everything on this page is drawn from published court records and news reporting, cited below. It is general information about how probate and trust law works — not legal advice, and not a prediction about any case. Reading it does not create an attorney-client relationship. Other states' law differs from Florida's, which is usually the whole point of the story.