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Michael Jackson told Martin Bashir he was worth over $1B. In 2009, he died more than $500M in debt. Las Vegas, 2002. "I remember getting $200,000 checks in the mail when I was like 12, 13 years old." Bashir asks what he's worth now. "It's way up there." "Come on, Martin. I've done really well." Over $1B? He says yes. Then his favorite store in town. "See, this is the shop. I bought so much stuff here." 2 urns. $275,000 each. Bashir guesses the bill at a couple of million dollars. The manager won't say. Later, Bashir put the day at $6M. To Bashir, it looks like Louis XIV's palace. "It's my taste." In 2005, a forensic accountant testified. His finances at the time of the documentary: $415M owed, about $130M in assets. He was spending $20M to $30M a year more than he earned. In June 2009, he died owing more than $500M. One question came before the shopping. "Have you always been good with your money?" "With my money? Yes."

Donald Trump charges $1M just to join Mar-a-Lago. Its first owner left it to America's presidents for free. In 1973, cereal heiress Marjorie Merriweather Post willed it to the US government as a winter retreat. In 1981, Washington gave it back. Too expensive to keep. Asking price: $20M. The buyer: Trump, 39. CBS asks if he paid $5M. "Well, you said that. I didn't say that." "I won't discuss that on national television." The full deal reportedly came to about $10M. At a table set with gold, he wonders: "What am I doing here? How did this happen?" He walks the crew through 118 rooms. "It's considered the number one home far and away in America." The early '90s. His Atlantic City casinos go bankrupt. He tells Palm Beach $3M a year in upkeep is too much for one owner. The town won't let him split the land into lots. In 1993, they agree on a private club. 500 members max. The entry fee climbs to $1M. Members can book suites for the night. In 2025, the club brought in $77.5M. Nearly 8x what he paid for the whole estate. Back then, the town feared a hotel casino. He told CBS: "I have no intention of doing anything like that."

Johnny Depp's telemarketing job was the opposite of "sell me this pen." In 2017, his former managers said he was spending $2M a month. In May 2017, he told Jimmy Kimmel how he started in LA, as a musician. "You had to pay clubs to play here." How much? "More than we had, for sure." His whole band ended up selling by phone. Overpriced ink pens, with a prize on every order. "A trip to Greece, or a grandfather clock." He found 1 buyer. A man ready to take 144 pens. Depp stopped him. "Sir, don't, don't, don't... don't buy this." "Because you're not going to Greece." The clock was "made out of like press board." Fired? "I took it upon myself to leave." 4 months before Kimmel, Depp sued his business managers for $25M. He said they mismanaged his money. He had earned over $650M. They sued back with a list. 14 homes for $75M. $200K a month on private jets. $30K a month on wine. $3M to fire Hunter S. Thompson's ashes out of a cannon. The same man once stopped a stranger from buying 144 pens. A year later, Depp answered the wine number. "It was insulting to say that I spent $30,000 on wine because it was far more."

Donald Trump called his $29M yacht "the jewel of yachting" in 1988. By 1991, $900M in personal debt, he had to sell it. Built for Saudi arms dealer Adnan Khashoggi. In 1983, it played the villain's yacht in Bond's "Never Say Never Again." Trump bought it from the Sultan of Brunei and renamed it Trump Princess. On deck, he told the press why he bought it: "I like to see the great jewels of the country being owned by the people of this country." "If you look at what Japan is doing, and if you look at what Saudi Arabia is doing... it's a shame for this country." Why call a 281-foot ship a "boat"? "To me, it's a boat because I'm modest." Inside: a 1,000-pound onyx bar. A private cinema. The buyer: Saudi prince Alwaleed bin Talal. He paid about $20M. The jewel went back to Saudi Arabia.

Dana White said Tito Ortiz was "out of his mind" for questioning his pay. In 2024, the UFC paid $375M to settle with fighters. 10 years into running the UFC, he gets asked about Tito. Tito claimed the UFC made $42M off one fight. His cut: $1.5M. "Let's say there was $42 million in revenue. Cut that in more than half." Early UFC stars made "1,500 bucks a fight." Top salaries today? "You'd be blown away." "These guys are making a lot of money. We are on par with all the other sports leagues." In 2014, the fighters sued. Their expert put UFC pay at under 20% of revenue. The NFL, NBA and MLB pay close to 50%. In March 2024, both sides agreed on $335M. The judge rejected it as too low. Fighters got under $250K each on average, after fees. Not one UFC contract had to change.

Vince McMahon told Bob Costas the XFL was "a viable business." 19 years later, his nearly $400M bet sold to The Rock for $15M. March 2001. HBO. The league is 6 weeks old. Ratings are down 75%. Costas asks about year 2. "I can't guarantee you that I'm going to be breathing in and breathing out after we leave the studio." "I'm pretty sure about the continuation of the XFL in one form or another." "I'm an entrepreneur. I take risk." "We didn't have any partners. We were going to do it all on our own." 57 days later, the WWF and NBC shut it down. They lost about $35M each. From 2017 to 2019, he sold about $395M of WWE stock to bring it back. 5 weeks into the 2020 season, COVID. April 2020, bankruptcy. August 2020, The Rock's group paid $15M. $395M of his own money. In 2001, he had a name for it: "Calculated risk."

Brad Pitt told Meet the Press his Katrina homes were 5 times stronger than code. 12 years later, the owners settled for $20.5M. In 2010, he hosted David Gregory in the Lower 9th Ward. His charity, Make It Right, planned 150 homes there. "We've got to make sure that these things are done right." The houses sat above the flood line. "5 times stronger than code." Affordable homes, he said, get the cheapest materials. "Do it right in the first place instead of this obsession with profit margin." The charity spent $26.8M on 109 homes. The wood rotted. In 2015, it sued the maker of its deck wood for nearly $500K. 39 homes needed new decks. In 2018, the owners sued Pitt over leaks, mold and rot. By 2022, 2 houses had been torn down. Each of 107 owners could claim $25K. The rest went to repairs. His forecast, in 2010: "I see this place as a template for the future."

Warren Buffett's son sold his Berkshire stock at 19 for $90,000. Today it would be worth $400M+. NBC, 2010. Peter Buffett sits next to his father on the Today show couch. He got the shares in 1977. "He didn't give it to us. It was from our grandfather." The money came from the sale of the family farm. Peter sold every share to buy time for music. Matt Lauer asks what they'd be worth now. His father answers. "Maybe $60 or $70 million." That was 2010. The stock is up almost 7 times since. Lauer: "Do you ever wake up in the middle of the night..." "I would much rather have my own success than live off his, frankly, even though it would have been a pile of money." In 2024, Warren signed a new will. More than 99% of his fortune, then about $130B, goes to a charitable trust run by his 3 children. Peter will help give it away. "In a sense, that's all it would have been."

Lance Armstrong collected $7.5M by swearing he never doped. 9 years later, the same oath cost him $10M. 2005. A Dallas company won't pay his $5M Tour de France bonus. It thinks he doped. He's under oath. A lawyer reads him Betsy Andreu's story. In 1996, he was in a hospital with cancer. She says he told doctors he'd used EPO, testosterone and steroids. Does he deny it? "One hundred percent." "She said in her deposition she hates me." Her husband Frankie backs her up. "I think he's trying to back up his old lady." "How could it have taken place when I've never taken performance enhancing drugs?" His own blood? "Absolutely. That would be banned." In 2006, SCA settled for $7.5M. In January 2013, he told Oprah he doped in all 7 Tour wins. In 2015, a panel ordered him to pay SCA $10M. "Perjury must never be profitable." The 2005 tape still has his answer: "How clear is that?"

Kanye West had 1 question for Jay-Z in 2005. 17 years later, he lost $1.6B in 1 day. Charlie Rose's studio, 2005. Rose asks about Jay-Z. "I would ask him, man, how'd you get all that money?" Then the real question. "And you know, how did you keep it?" "How did you run this company?" He remembers watching Jay-Z from the side of the stage. "This man is really a genius." In 2016, he tweeted he was $53M in personal debt. By 2022, his Yeezy deal with Adidas had made him a $2B man. On October 25, 2022, Adidas cut ties over his antisemitic remarks. Forbes dropped him to $400M. Jay-Z kept his. Forbes had him at $2.5B in 2025. Back in 2005, he'd said it himself. "I'm just a genius in training."

Mike Tyson told CNBC he "still had money" when he went bankrupt. His filing listed $23M in debt. 2013. CNBC asks where the $400M went. "I had bad business associates." "I had a lot of awesome cars, and I had great boats." Too much stuff? "Yeah, I did. Well, not really for the money I had." "I just trusted the wrong people." The 2003 filing listed $23M in debt. $17M of it was back taxes. "When I filed for bankruptcy, I wasn't still broke. I still had money." His memoir was his wife's idea. "Plus we need some money." In 2024, at 58, he fought a 27-year-old YouTuber. Reported pay: about $20M. He lost. Back in 2013, CNBC asked: "Can you make that money back?" "That's not necessarily my goal."

Prince wrote "SLAVE" on his face to fight his record label. 5 years after he died, a music company held 42% of his estate. 1996. Oprah asks about the word. "The slavery that I had undergone was in my mind." In 1992, his Warner Bros. deal was billed at $100M. 6 albums. A $10M advance on each, but only if the last one sold 5M copies. Prince: "That turned out to be a little less than desirable." "If you have any sort of chains on you, it's not going to come out as cool as it could be." April 2016. Prince dies at 57. No will. 6 heirs. 6 years in court. January 2022. The estate is valued at $156.4M. By then, Primary Wave, a music company, had bought most of 3 heirs' shares. 42% of the estate. In 1996, he told Oprah how his new album was made: "In a state of complete freedom."

Amber Heard promised a children's hospital $3.5M from her Johnny Depp divorce. It got $250K from her. October 2018. A Dutch talk show. The host: "People were saying this is all about the money." What did she do with her $7M settlement? "$7 million in total was donated." "I split it between the ACLU and Children's Hospital of Los Angeles." "More power to you," the host says. April 2022. Depp's $50M defamation trial. The ACLU got $1.3M under her name. $350K came from Heard herself. The rest included $500K from a fund tied to Elon Musk and $100K from Depp. Had she paid the hospital in full? "I have not yet." Her defense: pledge and donation mean the same thing. She said Depp's lawsuit stopped the payments. June 2022. The jury awards Depp $10.35M. December 2022. She settles for $1M. In 2018, she had one more line for the host: "I wanted nothing."

O.J. Simpson swore he would "never pay any dime" of a $33.5M verdict. Now his estate owes $58M and holds under $1M. July 2000. NBC's TODAY show with Katie Couric. 3 years after a civil jury found him liable in the deaths of Nicole Brown Simpson and Ron Goldman. The families got $400K from an auction of his memorabilia. He still owes about $33M, and it grows with interest every year. "I will never pay any dime to that verdict." Why did they get $400K? "I didn't give it. I had no choice. That was taken from me." He lives on a $20K to $25K monthly pension. The families can't touch it. Next, he's moving to Florida, where his house can't be seized. "There are certain laws that benefit people in my position." Will he avoid a job, so the money doesn't go to the families? "If I had to work to fund what I believe is a wrong decision, I probably would not work." He died in April 2024, at 76. His executor first said he hoped the Goldmans would get "zero, nothing." The Goldmans claimed $117M. In November 2025, the executor accepted $57,997,858. He says the estate is worth under $1M. Their lawyer: acceptance "does not constitute payment." In 2000, Simpson told Couric: "I don't believe I owe anything."

Floyd Mayweather told Jimmy Kimmel he was "the human ATM." 8 years later, he was charged over a $200K check that bounced. August 2017. 11 days before the Conor McGregor fight. "I feel like money." His payday for 1 fight? "350 million." Kimmel shows a photo of Floyd on a plane, surrounded by cash. Does he even have an ATM card? "I'm the human ATM." "When you order millions of dollars, a Brinks truck comes to your home." He once owned one. Sold it. To who? "Another guy who loved money." In February 2026, he sued Showtime, claiming at least $340M of his $1.2B in purses went missing. Almost the $350M he said 1 fight would pay. In April 2026, Las Vegas prosecutors charged him with 2 felonies. A $200K check, written in December 2024, for an Audemars Piguet watch. His lawyer says there was no intent to defraud. In 2017, Kimmel asked if he really uses the cash. "Cash is key."

The Godfather director put $120M of his own money into his dream film. 10 months later, he said he had none. Cannes, May 2024. A reporter asks Francis Ford Coppola, 85, about the risk. “I don’t care. I never cared about money.” He sold part of his wine business to pay for Megalopolis. His kids, Sofia and Roman, “don’t need a fortune.” “We’re fine. It doesn’t matter.” September 2024. Megalopolis opens. It makes about $14M worldwide. Less than 12 cents for every dollar he put in. March 2025. Rick Rubin’s podcast. “I don’t have any money.” 7 months later, he puts his watches up for auction. “I need to get some money to keep the ship afloat.” In December, his custom F.P. Journe sells for $10.8M. At Cannes, he had told the room: “Money may evaporate.”

Jack Ma told 60 Minutes he never took a cent from Beijing. In 2020, one speech cost him a $34.5B IPO. Fall 2014. Alibaba had just listed in New York at $231B. His order for investors: "Customer number one, employee number two, shareholder number three." And the government? "I never got one cent from government. I never got one cent from China banks." His rule for the team: "Never, ever do business with government. We love them. Don't marry them." In October 2020, Ma criticized China's regulators on stage in Shanghai. 10 days later, the IPO was dead, 2 days before it was set to list. It would have been the biggest ever. Ma vanished from public view for almost 3 months. In April 2021, Alibaba got a record $2.8B fine. By 2023, shareholder number three had lost $620B from the 2020 peak. Ma's fortune fell from $61B to $34B. Back then, he had explained how he kept the state happy: "We keep a very good love relationship with the government."

Stormy Daniels’ lawyer Michael Avenatti told CNN he wasn’t broke. He’d hidden a paraplegic client’s $4M. In 2019, out on bail, he sat down with CNN’s Sara Sidner. Prosecutors said he had cheated 5 clients. Did he defraud the client? His lawyers told him to stay quiet. The private jet? “I had an interest in a private jet, yes.” “Have I had a privileged lifestyle? Of course.” “I’m a self-made guy... I busted my ass for a lot of what I have received.” Then the question. “Are you broke?” “No, I’m not broke.” The client, Geoffrey Johnson, won $4M from LA County. Avenatti never told him. Johnson got “advances” of $1,000 to $1,900. In 2022, a jury found he’d also taken nearly $300K from Stormy Daniels. He pleaded guilty in the client case: 14 years, on top of 5 from New York. Over $7M owed to clients, over $3M to the IRS. In 2025, the sentence was cut to about 11 years. He’d told Sidner where his money came from. “Nothing was ever handed to me, Sara.”

Forbes named Kylie Jenner, 21, the youngest self-made billionaire. 14 months later, it said her company's tax returns were "likely forged." July 2018. Forbes puts her on its cover at $900M, on her way to $1B. September 2019. On Ellen, Kris Jenner beside her. Ellen asks if the money changed her. "I could get a new car any time." Her sisters joke about it in the group chat. "Kylie, question mark, are you going to pay for it?" Kylie Cosmetics, the family told Forbes, did $360M in 2018. They'd shown Forbes tax returns to back up the numbers. In November 2019, Coty paid $600M for 51%. Then Coty's numbers came out: about $125M for 2018. In May 2020, Forbes ran "Inside Kylie Jenner's Web of Lies." Its new estimate: just under $900M. Right back where the cover started. The happiness of a new car, she'd said, "only lasts so long."

Scooter Braun got Taylor Swift's first 6 albums in a $300M deal. In 2025, she bought them back. Summer 2019. Braun's company buys her old label, Big Machine. Her masters come with it: the original recordings of 6 albums. Her old label boss says she knew. That she'd been offered the chance to buy. That her dad, a Big Machine investor, knew too. Her dad's cut: a reported $15.1M. She remembers it differently. Did anyone close to her know? "Nobody knew." "I knew he would sell my music. I couldn't believe who he sold it to, because we've had endless conversations about Scooter Braun." "He has 300 million reasons to conveniently forget those conversations." Could she re-record? "Oh, yeah. That's a plan. Absolutely." November 2020. Braun sells her masters to Shamrock for a reported $300M+. From 2021 to 2023, she re-records 4 of the 6 albums. May 2025. She buys all 6 back for a reported $360M. She wrote: "All of the music I've ever made... now belongs... to me."