← The Probate Archive
— How it went wrong · 31 cases
Capacity & undue influence
Eccentricity is not incapacity, and generosity is not undue influence. The legal question is never whether a gift was odd — it is whether someone in a position of trust took hold of the pen. Florida answers that question more favourably to challengers than most states do.
— The Florida law this runs into
A will procured by fraud, duress, mistake, or undue influence is void.
The crucial one: the presumption of undue influence shifts the burden of PROOF, not merely production.
In re Estate of Carpenter, 253 So. 2d 697 (Fla. 1971)
The presumption, and the non-exclusive indicators of active procurement.
No-contest clauses are unenforceable, so challenging costs a beneficiary nothing.
— 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.
Two wills, six weeks apart· 9-min read
Huguette Clark
A copper heiress worth $300 million spent the last twenty years of her life in a hospital room by choice, while her mansions sat empty and staffed. Then she signed two wills six weeks apart that said opposite things — and nineteen relatives who had never met her went to court.
The $30 million he could not keep· 9-min readFlorida
Abraham Shakespeare
A Lakeland truck driver's assistant won a $30 million Florida Lotto jackpot in 2006 and took $17 million in cash. Within three years the money was gone, his house was titled to someone else's company, and he was dead. The estate spent four more years getting the house back for his two sons.
Convicted of paperwork· 9-min readFlorida
Al Capone
The federal government never proved Al Capone did the things he is remembered for. It proved he had not paid his income tax. He died on Palm Island in Miami Beach in 1947 still owing that government money — and the house everyone calls Capone's mansion was bought in his wife's name.
The son went to prison· 10-min read
Brooke Astor
Nearly every case in this archive ends in a settlement, because civil courts divide money and rarely assign blame. This one ended differently. A Manhattan jury convicted her only son of looting her estate, an appellate court affirmed, and at 89 he reported to state prison.
The countdown that ended in Oslo· 9-min read
Casey Kasem
The most familiar voice in American radio spent his last month as the subject of a conservatorship fight, a court order about a feeding tube, and a search across two states. Then, six months after his death, his body was buried in Norway.
Four months in a county morgue· 9-min readStill open
Charles Manson
He died in a Bakersfield hospital in 2017. A claimed son, a claimed grandson, and a memorabilia collector holding a two-page will all filed for the body. It sat in the county morgue for four months while a court sorted out who ranked highest. The estate case is still going.
Ninety-five percent to one son· 9-min read
Cornelius Vanderbilt
The Commodore died in 1877 leaving the largest fortune in America — and left roughly ninety-five percent of it to a single son. Three of his other children went to court alleging insanity, spiritualists, and undue influence, and New York read the transcript over breakfast for more than a year.
The butler was the executor· 10-min read
Doris Duke
The richest girl in the world died in 1993 leaving roughly $1.2 billion, almost all of it to charity — and named as executor the butler she had hired six years earlier. Three years of Manhattan Surrogate's Court litigation followed, and it produced a rule that still governs how easily a court may fire the person a will chose.
Two pages and a misspelled name· 10-min read
Elvis & Lisa Marie Presley
A one-page amendment nobody witnessed removed Elvis's widow as trustee of his daughter's trust — and spelled her name wrong. Eleven months after the settlement, a stranger published a notice in a Memphis paper announcing the foreclosure sale of Graceland.
The crime that happens inside the family· 9-min readFlorida
Exploitation of the elderly
Florida wrote a separate felony for taking an older person's money from a position of trust. It is graded by dollar value, it reaches the power of attorney and the joint account, and it comes with a reporting duty that lands on bankers and nurses before it ever reaches a prosecutor.
The chihuahua with the Escalade· 8-min readFlorida
Gail Posner
A Miami Beach heiress left her waterfront mansion and a reported $3 million trust to three dogs, and roughly $26 million to the household staff who cared for them. Her son received $1 million and filed suit. The house sold for $8.4 million.
The codicil at 96· 9-min read
Georgia O'Keeffe
A 27-year-old potter knocked on the door at Ghost Ranch looking for odd jobs. O'Keeffe was 85. Eleven years later a codicil moved the residuary estate — reported at $47.2 million — from charity to him. Her sister and her niece went to court, and the answer arrived as a settlement rather than a verdict.
The test is the relationship, not the recipient· 10-min readFlorida
Gifts to religious organisations
A relative discovers that most of an estate went to a congregation. The instinct is to argue about the organisation. Florida courts do not. They ask three questions about relationship, benefit, and procurement — and the answers would be identical if the recipient were a university, a caregiver, or a nephew.
The conservatorship decided a month before he died· 9-min read
Groucho Marx
At 86 he was the subject of a public court fight over who would control him: his companion and manager, or his son. A judge finally handed the job to his 27-year-old grandson three weeks before he died. Six years later a jury ordered the companion to repay the estate $471,842.
The will they sealed· 9-min read
Harper Lee
Lee published one novel, then nothing for fifty-five years — until a second manuscript surfaced in a safe-deposit box when she was 88. She died the following February. Her will went under seal in an Alabama probate court, and a newspaper had to sue to read it. What it revealed was a trust nobody can read at all.
The law written for one marriage· 9-min readFlorida
Henry Flagler
Flagler built Standard Oil with Rockefeller, then built Florida — the railway, Palm Beach, Miami, Key West. In 1901 the Florida legislature made incurable insanity a ground for divorce. He was the only person ever divorced under it. It was repealed in 1905.
Thirty downstrokes, one in a sextillion· 9-min read
Hetty Green
Before she became the richest woman in America, Hetty Green sued her aunt's estate over a disputed page said to leave her everything. The defence hired a Harvard mathematician, who calculated the odds that the signature was genuine at roughly one in 2.666 sextillion. It is the first great use of statistics as evidence in an American courtroom.
The seven warning signals· 9-min readFlorida
In re Estate of Carpenter
A Florida widow signed a will four days before she died, leaving everything to the daughter who had arranged it and nothing to her three sons. The Supreme Court of Florida used the case to write the list of warning signs that every Florida will contest has been argued around ever since.
Thirty-nine days· 10-min read
J. Seward Johnson Sr.
The Johnson & Johnson heir signed a will leaving essentially everything to his third wife — a Polish immigrant who had entered the household as domestic staff — and died five and a half weeks later at 87. His six children spent fifteen weeks in a Manhattan courtroom trying to undo it.
Twenty-seven, and no paperwork· 9-min read
Jimi Hendrix
He died at 27 without a will, so everything went to a father who had barely raised him. It took that father twenty-five years and a lawsuit to get the rights back — and then his own will started a second war between a son and an adopted daughter.
“For reasons which are well known to them”· 8-min read
Joan Crawford
She adopted four children and left two of them nothing, in eleven words that gave no reason and started a two-year fight. The disinherited pair objected to probate on capacity and undue influence. The estate paid $55,000 to make it stop.
One lawyer, three jobs· 9-min readFlorida
Joe DiMaggio
DiMaggio died in Hollywood, Florida in 1999. The lawyer who had represented him for two decades was named personal representative, initial trustee, and the person who would control the licensing of his name — all in a will that lawyer's own office was involved in producing. Then came the books, the tapes, and a federal grand jury.
The house he promised out loud· 8-min read
Marlon Brando
He bought the house in 2002 and kept it in his own name. The woman who ran his household said he had promised to sign the deed over before he died. He never did — and an unwritten promise about real estate is, in almost every American state, a story rather than a contract.
Ninety years of work, $18,000 left· 9-min read
Mickey Rooney
In March 2011 a 90-year-old man who had been making films since the Coolidge administration sat down in front of a United States Senate committee and described being unable to get information about his own money. Three years later he died. The estate came to eighteen thousand dollars.
The will that was a forgery· 10-min read
Nina Wang
She spent a decade in court proving that a will benefiting somebody else was forged. She won. Then she died, and a one-page document appeared leaving her multi-billion-dollar estate to her feng shui consultant — and Hong Kong's courts spent six more years deciding it was forged too.
The guardianship scandal· 10-min readFlorida
Rebecca Fierle
She held the largest professional guardianship practice in Florida — more than 400 wards across 19 counties. One ward's death in a Tampa hospital in 2019 unwound all of it, and produced a statewide investigation, a criminal case, and a rewrite of Chapter 744.
The death nobody mentioned· 9-min readFlorida
Schilling v. Herrera
Mignonne Schilling died in Miami in August 2004. Her brother — the sole beneficiary of her 1996 will — was not told until December 6, four days after her caregiver had petitioned to close the probate. By then there was nothing to contest. So he sued in tort instead, and Florida's Third District let him.
The estate fight he lived to see· 10-min read
Sumner Redstone
Most probate litigation starts with a funeral. Redstone's started in 2015, while he was 92 and very much alive, when a former companion asked a Los Angeles court to declare him incapable of having removed her. Four years of litigation followed, in three states, over a trust that had not yet begun.
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.
Two notes nobody could read· 9-min read
Thomas Kinkade
Against a formal will, three codicils and a trust, his girlfriend produced two handwritten pages dated a month apart. They gave her the house and $10 million. The handwriting was close to illegible. His estranged wife — never divorced — was on the other side.
— The other ways it goes wrong
Died without a willHandwritten willsTrustee & fee warsPetsStrange conditionsRemains & 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.