Richard Hatch won $1,000,000 on the first season of Survivor. The IRS says he now owes $3.3 million on it.
51 million people watched him win in August 2000. He never paid the tax on the prize.
His defense: he says he caught producers sneaking food to other players, and the show promised to cover his taxes if he won. CBS never commented. The appeals court said he never showed any proof of a deal.
In 2006 a jury convicted him. He served 51 months in federal prison. In 2011 he went back for nine more, for not fixing his returns.
Then the bill kept growing.
This March, 26 years after the finale, a federal judge let the IRS collect about $3.3 million with interest. The government put liens on two of his homes in Newport. He is appealing on his own, without a lawyer.
In the video below he explains why he thinks the tax was never his to pay.
"The taxes on the million were required by law… to have been paid to Malaysia before we left the island… by CBS or Mark Burnett."
The case for Hatch: if the show made that promise, he was set up. The case for the IRS: a $1 million check is income. Everyone else pays theirs.
Was the first Survivor winner played by the show, or did he try to outwit the wrong player?
Marilyn Monroe made about $4 million in her entire career. A woman who married her acting teacher six years after she died made at least $40 million from her name.
In the video below, two years before her death, Marilyn is asked if she is happy.
"If I'm generally anything, I guess I'm generally miserable."
Her will left her clothes and personal things to her acting coach, Lee Strasberg, with one request: "it being my desire that he distribute these, in his sole discretion, among my friends, colleagues and those to whom I am devoted."
He also got 75% of everything else. Her psychiatrist got 25%. Her half-sister got $10,000. Her mother, in an institution, got a $100,000 trust.
In 1968 Strasberg married Anna Mizrahi, a 28-year-old actress. When he died in 1982, Anna inherited three quarters of Marilyn.
In 1999 she sold Marilyn's belongings at Christie's for $13.4 million. The "Happy Birthday, Mr. President" dress went for $1.26 million.
She licensed Marilyn's face to vodka, lingerie and slot machines. In 2011 she sold the rights for a reported $20 to $30 million.
The case for Anna: Marilyn left it to Lee. Lee left it to his wife. That is how a will works. The case for Marilyn: she asked for her things to go to the people she loved. They went to the highest bidder.
Did Anna Strasberg do anything wrong, or did Marilyn's will do exactly what it said?
Lori Loughlin paid $500,000 to get her two daughters into USC as rowers. Neither of them rowed.
In the video below, one of them explains what she wanted from college.
"I do want the experience of like game days, partying. I don't really care about school, as you guys all know."
Lori and her husband, designer Mossimo Giannulli, paid a college consultant to have both girls listed as recruits for the USC crew team. The family staged photos of them on rowing machines.
In 2019 the FBI arrested them. Lori served two months in prison and paid a $150,000 fine. Mossimo served five months and paid $250,000.
She lost her Hallmark movies and her role on Fuller House.
Last month, after almost 29 years of marriage, Lori filed for divorce. She asked the court to split everything under their prenup, signed in 1997 and changed in 2015.
This week Mossimo answered. His filing doesn't mention the prenup. It asks the court to decide whether either of them should pay the other spousal support, and whether one should cover the other's legal fees.
$500,000 to buy two spots at USC. Now the fight is over what's left.
Did they get what they paid for, or did that $500,000 end up costing them everything?
Beyonce’s father replaced two members of Destiny’s Child and never told them. They found out from the “Say My Name” video. Their voices. Someone else’s faces.
In the video below, he mocks the girl who replaced them, the one he says walked away from $50 million.
“Somebody left a group, left fifty million dollars on the table, because Mathew Knowles got loud… Oh my goodness.”
Mathew Knowles managed the group. LeToya Luckett and LaTavia Roberson had asked him for a different manager. They said he favored his daughter and kept too much of the money.
In February 2000 the video came out. Two new girls were on screen, mouthing the words LeToya and LaTavia had recorded. They sued him. They settled.
One of the new girls, Farrah Franklin, lasted five months. That is who he is talking about.
“I’m gonna make sure I don’t get loud on this interview anymore. I might offend you, man.”
Destiny’s Child went on to sell more than 60 million records.
In 2011 Beyonce cut him loose as her manager. According to his own court filing, Live Nation told her he had taken money he wasn’t entitled to. He denies it.
Last December, Forbes declared Beyonce a billionaire.
Was Mathew Knowles the tough manager who built Beyonce, or did he burn everyone who trusted him, including his own daughter?
Michael Jackson’s will has one line for the mother of two of his children: “I have intentionally omitted to provide for my former wife, Deborah Jean Rowe Jackson.”
Everything else went into a trust, run by two men he named. One of them, John Branca, was a lawyer Michael had fired more than once.
In the video below, his daughter Paris talks about meeting her mother for the first time. She was 15.
“I came in and I was just like, ‘Hey, Mom.’”
When Michael died in 2009, he owed more than $500 million. His trust splits what’s left: 40% to his mother, 40% to his three children, 20% to charity.
The estate says it has since earned billions for his kids.
Paris says the two executors were paid $148 million from her father’s estate through 2021. In 2021 alone, more than double what any of his children received, her filing says. And $464 million of the estate is sitting in cash, earning less than 0.1%.
In May a judge ordered $625,000 in bonuses, which the executors paid out to other law firms, returned to the estate.
Her lawyers say Branca told the court he’d rather the family “just said ‘thank you’ and went on your way.”
This year he helped produce the Michael biopic. Miles Teller plays him. Paris called the film “sugar-coated.”
The executors’ answer: Paris herself has received about $65 million from the estate, money they say would never have existed without them.
Did John Branca save Michael Jackson’s fortune, or is he getting rich off his children?
O.J. Simpson owed $33.5 million to the families. Ron Goldman's father offered to drop every dollar of it if O.J. would just sign a confession. O.J. said no.
Nine years later he told the story on camera anyway. For a book deal.
In the video below, he tells it.
"I'm gonna tell you a story you've never heard before."
He was acquitted of the murders in 1995. In 1997 a civil jury found him liable for the deaths of Nicole Brown Simpson and Ron Goldman and ordered him to pay $33.5 million.
Days later, Fred Goldman made his offer: a signed confession, broadcast across the country, and the judgment disappears. O.J.'s answer through his lawyer: "I would never confess to a crime which I did not commit."
In 2006 he sat down for a book called "If I Did It." He walked through the night, "hypothetically." The publisher paid $630,000, routed through a company in his children's names.
Asked if it was blood money, he said: "Every book that was written about this case was blood money."
A bankruptcy judge called the company a sham and handed the book to the Goldmans. They published it as "If I Did It: Confessions of the Killer."
O.J. said he lived on his NFL pension, which the families couldn't touch. He played golf in Las Vegas almost every day.
He died in 2024. His executor said: "It's my hope that the Goldmans get zero, nothing."
With interest, the debt had grown to $117 million. His estate says it's worth $500,000 to $1 million. Less than a penny on the dollar.
Should Fred Goldman have taken the confession, or was the money the only way to make him pay?
Whitney Wolfe Herd helped build Tinder, left at 24 with a harassment lawsuit, and built a rival worth $14 billion. This week it sold for $1.3 billion.
In the video below, she talks about how it started.
"How am I ever going to escape this? I was 24 years old."
In 2014 she sued Tinder. Her lawsuit said a co-founder she had dated called her a "whore" at a company event, and that her co-founder title was taken away. Tinder settled without admitting wrongdoing.
Months later she launched Bumble. One rule: women message first.
In 2017 Match Group, the company that owns Tinder, offered $450 million for Bumble. She said no. Match sued. Bumble answered with a full-page ad in The New York Times: "We swipe left on you. We'll never be yours. No matter the price tag."
In 2021 she rang the Nasdaq opening bell with her toddler son on her hip. She was 31, the youngest woman ever to take a US company public. Bumble ended its first day worth about $14 billion, and Forbes put her at $1.5 billion.
Then the stock fell for five years. From $78 a share to about $2.50.
Do the math. $10,000 of Bumble bought at the end of its first day is worth about $860 at this week's price.
Last month, on stage, she said Bumble would matter more in 15 years "than it was at its height in the stock market."
Four weeks later, Bumble agreed to be sold for $6.05 a share.
Did "women message first" stop working, or are dating apps just dead?
Elon Musk's team offered the mother of his child $40 million to never talk about him, she says. She said no.
In the video below, Ashley St. Clair says it out loud.
"I was offered the opportunity not to speak for $40 million."
She says the offer came through Jared Birchall, the man who manages Elon Musk's money.
The Wall Street Journal reported how it was built. $15 million up front. Then $100,000 a month until their son turns 21.
Do the math. $100,000 × 12 × 21 years is $25.2 million. Plus $15 million. About $40 million, in exchange for silence.
She didn't sign. Instead she went on camera for a documentary about him, out at the end of this month.
Musk says the offer never happened and that she "has a history of making false claims."
Two days ago he posted: "Ashley St Clair was not my girlfriend. We only saw each other a few times."
"I want to set the example for my kids," she says, "that you should never take being materially comfortable over speaking the truth."
Would you have taken the $40 million, or is she right to talk?
Diddy made more than $1 billion from a vodka that was selling 40,000 cases a year when he took it over. Now his own lawyers say he stopped paying them.
In the video below, he explains the deal himself.
"I told him, I want to be an owner."
In 2007 Diageo, the biggest spirits company in the world, asked him to promote Ciroc. Instead of a flat fee, he took a share of the profits.
"I took it to 2.6 million cases from 40,000 cases," he says. "This is something that's never been done."
Diageo later said in court that it had paid him more than $1 billion between 2007 and 2023.
Then it fell apart. In 2023 he accused Diageo of treating Ciroc as an "urban" brand. Diageo said he broke the deal. The partnership ended.
In 2025 he was sentenced to 50 months in federal prison.
In September, his lawyers asked a judge to let them quit his $100 million defamation case, saying he hadn't paid them in more than six months. He says they overcharged him.
Last week, a judge ordered him to pay NBCUniversal $477,700 in legal fees after he lost another $100 million lawsuit.
This week, TMZ reported he was rushed from prison to a hospital.
He asked to be an owner, not a spokesman. The billion came. The lawyers are still waiting.
Was Ciroc one of the best deals in music history, or was that fortune never really his?
Peter Thiel spent about $10 million in secret to wipe out a media company that had outed him. His weapon was Hulk Hogan's sex tape.
In the video below, Thiel explains why he did it.
"If you make a sex tape of someone with their permission, you are a pornographer. If you make a sex tape without their permission, we were told, now you are a journalist."
It started in 2007. A Gawker blog ran a headline: "Peter Thiel is totally gay, people." He later called that blog the Silicon Valley equivalent of Al Qaeda.
In 2012, Gawker posted a clip of Hulk Hogan having sex with his best friend's wife.
Hogan sued. Nobody knew who was paying his lawyers.
In 2016 a Florida jury awarded him $140 million. Gawker went bankrupt and was sold for $135 million.
Only then did the name come out. Thiel said it was "less about revenge and more about specific deterrence," and called it "one of my greater philanthropic things that I've done."
Hogan settled for $31 million. Thiel's name never came up at the trial.
About $10 million in legal fees, and a company that spent years exposing the rich was gone.
Was it justice for a man whose bedroom was put on the internet, or a billionaire using his money to kill the press?
Willie Nelson was 57 when the IRS took almost everything he owned. His ranch, his recording studio, his gold records. The bill was $16.7 million.
They missed one guitar. His daughter had already shipped it to Hawaii.
In the video below, Willie explains how one man gets into that much trouble.
"I'm not the best businessman in the world. I think it's important that you trust someone to do these things for you."
He trusted the accountants at Price Waterhouse. In the 80s they put his money into tax shelters. The government later threw them out, and the bill came with penalties and interest.
"Since 1983 I've paid $8 million in taxes," he says. "I'm not a tax dodger."
Then his fans showed up. Farmers he had helped through Farm Aid bought his ranch at auction so they could give it back.
He recorded an album with just his guitar and sold it by phone for $19.95. It was called The IRS Tapes. It raised $3.6 million.
He sued Price Waterhouse for the rest and settled. By 1993 he owed nothing.
Was Willie a tax cheat, or a musician who trusted the wrong accountants?
Whitney Houston signed a $100 million record deal in 2001. A year later, her own father sued her for $100 million.
In the video below, Whitney tells Oprah what was really going on: "My dad was being influenced by people that were lying to him. He was in the hospital. I was paying the bills."
She was paying her father's bills while his company was suing her.
The company said it had helped negotiate her deal with Arista Records and helped get a marijuana charge against her in Hawaii dropped. It wanted to be paid.
At 82, from his hospital bed, he went on TV with a message for her: "You get your act together, honey, and you pay me the money that you owe me."
They didn't speak for years. When he got really sick, she went to the hospital and told him to end it.
Two months after that TV interview, he died.
The lawsuit didn't. His business partner kept it going until a judge threw it out in 2004.
Was he a father asking for what he earned, or a father cashing in on his daughter?
Forbes named Kylie Jenner the youngest self-made billionaire in history. She was 21. A year later, Forbes said her family had lied about her business for years and took the title back.
In the video below, Kylie tells Forbes how she built it.
"I'm the face of my brand, and I take responsibility for everything that happens."
At 18 she started selling $29 lip kits. In 2019 Coty, the company behind CoverGirl, bought 51% of Kylie Cosmetics for $600 million.
That deal is what exposed her. Coty is a public company, so it had to publish the real numbers.
Forbes compared them with what the family had been telling its reporters since 2016. The business was smaller and less profitable. Forbes wrote that the tax returns it had been shown were likely fake. Her lawyer called that unequivocally false.
She still walked away with an estimated $340 million after tax.
In the same video she says her mom "has definitely been a huge part of the success of Kylie Cosmetics."
In August she defended the title again: "None of the money I've ever made is inherited, so it's technically true."
She didn't inherit money. She inherited an audience.
Is Kylie Jenner self-made, or was she born rich?
J. Seward Johnson, heir to Johnson & Johnson, left his wife for the family's maid and left her almost his entire fortune. His six children got nothing.
In the video below, his grandson Jamie Johnson tells the story himself, in Born Rich, the 2003 film he made about kids like him.
"When my grandfather was 73, he left my grandmother and married the upstairs maid."
Her name was Basia Piasecka. She came to America from Poland in 1968 with about $100, and his wife hired her as the family cook.
Three years later she was his wife. He was 76. She was 34. None of his children were invited to the wedding.
He signed his last will in April 1983, weeks before he died of cancer at 87. Nearly everything went to her.
The children sued. They said a sick old man had been manipulated. Her side said the children only cared about his money. The trial lasted 15 weeks.
It ended in a settlement. She kept $300 million. The six children split $42.5 million.
His reason for cutting them out: he believed he had already given them enough Johnson & Johnson stock to be set for life.
She arrived with $100. By 2007, Forbes put her at $2.7 billion.
Was she a gold digger, or did she earn every dollar?
Ivanka Trump was about 10 when her father pointed at a homeless man outside Trump Tower and told her the man had $8 billion more than he did.
In the video below, she tells the story herself, in Born Rich, the 2003 film made by an heir to Johnson & Johnson.
"I remember my father pointing to him and saying, 'You know, that guy has $8 billion more than me,' because he was in such extreme debt at that point."
He wasn't joking. At the start of 1990, Donald Trump owed more than 70 banks about $4 billion. $800 million of it he had guaranteed personally.
The banks didn't take everything. They put him on an allowance. $450,000 a month for personal spending, less in the years after.
There's an old saying on Wall Street. Owe the bank $100, and it's your problem. Owe the bank $4 billion, and it's the bank's problem.
The man on the sidewalk owed nobody anything. On paper, he really was richer.
The richest-looking man on Fifth Avenue was worth less than the one sitting outside his own front door.
Was he broke, or was he just too big for the banks to let him fall?
Paul McCartney taught Michael Jackson the smartest move in the music business: buy the rights to songs. In 1985, Michael bought Paul's. $47.5 million for more than 250 Beatles songs.
In the video below, Paul tells Howard Stern what happened next, and you can hear how much it still bothers him.
They had just made hits together. Paul explained how publishing works: whoever owns a song gets paid every time it's played, sold or used. Michael told him, "I'm gonna get yours." Paul thought it was a joke.
Then the call came. Michael had them.
Years later Paul wrote to him: "After 30 years of being reasonably successful for this company you now own, don't you think I could have a raise?"
Michael's answer: "Oh well, that's just business."
After that, Paul says, Michael stopped answering his letters.
In 2016, Michael's estate sold its half of the catalog company to Sony for $750 million. Paul had to sue Sony in 2017 to start getting his own songs back.
Paul gave a friend the best business advice of his life. The friend used it on him.
Was Michael just doing business, or did he betray a friend?
Save the video, and follow for more money stories from behind the world's biggest names.
Mark Cuban's dad upholstered car seats his whole life and never made more than $40,000 a year.
When Mark told him he had $100,000 in the bank, his father started crying.
This is how Mark remembers him: "My dad was like, 'I don't know what the f*** you're doing, but keep on doing it.'"
In the video below, Mark tells Theo Von the whole story, including how his dad lost an eye at work.
Norton Cuban stapled fabric onto car seats in Pittsburgh. One day a staple broke and hit him in the eye. Mark was about 11. His dad wore a glass eye after that and kept going to work.
Mark paid for his own college. He sold garbage bags door to door at 12. Years later he became a billionaire.
But the number that made his father cry was 100,000.
It's easy to say money doesn't buy happiness and just as easy to see what that number meant to a man who never got near it.
Charlie Munger said the first 100,000 is the hardest. The math agrees with him.
Put away 1,000 dollars a month at 7 percent. The first 100,000 takes about 6.7 years. The second takes 4.5. The third takes 3.4. Same 1,000 a month. The money just starts doing more of the work.
At 100,000, your money earns about 7,000 a year without you lifting a finger. For Norton Cuban, in his best year, that was two months of stapling car seats.
His son made billions. The moment his dad cried over was the first 100,000.
How old were you when you hit your first 100,000, or are you still on the way?
Sandy Gottesman, one of Warren Buffett's first investors, left his wife a fortune in Berkshire Hathaway stock she didn't know existed.
At 93, Ruth Gottesman walked up to a podium in the Bronx and gave 1 billion dollars of it to a room full of medical students. Watch their faces in the video below.
Her husband's only instruction had been one sentence:
"Do whatever you think is right with it."
Tuition at the Albert Einstein College of Medicine was more than 59,000 dollars a year. Over four years, that is about 236,000 dollars per student.
She told them it was now free. Forever. That is the second the room stands up.
The money came from one decision Sandy made decades earlier. He met Buffett in 1963, put money into Berkshire early, and barely touched it. By 2012 he estimated his shares had grown about 6,000 times.
That is roughly 22 percent a year, every year, for 44 years.
He died in 2022, after 72 years of marriage. In her words, he left her "unbeknownst to me, a whole portfolio of Berkshire Hathaway stock."
The Gottesmans had three children and seven grandchildren. The billion went to strangers.
It's easy to admire and just as easy to question. Hundreds of future doctors without debt. And one person deciding where a billion dollars goes.
He spent half a century growing it. She decided what it was for.
Would you have left the billion to your grandchildren, or done what she did?
Verax retweeted
In 1939, a retired legal secretary in Vermont dropped by a government office while running an errand. She had paid 24.75 dollars into a brand new federal program.
It paid her back 22,888 dollars. Years later she explained that visit in one sentence:
"It wasn't that I expected anything, mind you, but I knew I'd been paying for something called Social Security and I wanted to ask the people in Rutland about it."
Her name is Ida May Fuller. On January 31, 1940, the government mailed her check number 00-000-001, the first monthly Social Security check in American history. 22.54 dollars.
She was 65. She lived to 100. By the end she had collected more than 900 times what she paid in.
Honestly, most of us plan the opposite way. Take the money as early as possible, because who knows how long we've got.
That instinct is the expensive one. On a 3,000 dollar full benefit, claiming at 62 pays 2,100 a month. Waiting until 70 pays 3,720. Waiting gives up 201,600 dollars of checks, and the bigger check wins all of it back by about 80.
"But life expectancy is 78." That's at birth. Social Security's own life table says a man who reaches 62 lives on average to 82, a woman to 85. Live to 90 and waiting paid you 187,200 dollars more, in today's money.
Married, it gets bigger. The survivor can keep the larger of the two checks. For a husband and wife who both reach 62, the chance that at least one of them is alive at 85 is about 74 percent.
So the move is one line on one form: the higher earner files for 70. Claim at 62 only if your health is poor or you need the money now to stay out of debt.
She wasn't lucky to live that long. She was insured against it.
Below, Peter Diamond, the MIT Nobel laureate who spent decades on how Social Security should work.
When are you claiming, 62 or 70?
In 1939, a retired legal secretary in Vermont dropped by a government office while running an errand. She had paid 24.75 dollars into a brand new federal program.
It paid her back 22,888 dollars. Years later she explained that visit in one sentence:
"It wasn't that I expected anything, mind you, but I knew I'd been paying for something called Social Security and I wanted to ask the people in Rutland about it."
Her name is Ida May Fuller. On January 31, 1940, the government mailed her check number 00-000-001, the first monthly Social Security check in American history. 22.54 dollars.
She was 65. She lived to 100. By the end she had collected more than 900 times what she paid in.
Honestly, most of us plan the opposite way. Take the money as early as possible, because who knows how long we've got.
That instinct is the expensive one. On a 3,000 dollar full benefit, claiming at 62 pays 2,100 a month. Waiting until 70 pays 3,720. Waiting gives up 201,600 dollars of checks, and the bigger check wins all of it back by about 80.
"But life expectancy is 78." That's at birth. Social Security's own life table says a man who reaches 62 lives on average to 82, a woman to 85. Live to 90 and waiting paid you 187,200 dollars more, in today's money.
Married, it gets bigger. The survivor can keep the larger of the two checks. For a husband and wife who both reach 62, the chance that at least one of them is alive at 85 is about 74 percent.
So the move is one line on one form: the higher earner files for 70. Claim at 62 only if your health is poor or you need the money now to stay out of debt.
She wasn't lucky to live that long. She was insured against it.
Below, Peter Diamond, the MIT Nobel laureate who spent decades on how Social Security should work.
When are you claiming, 62 or 70?