In 2024, Shohei Ohtani found out his interpreter had stolen nearly $17 million from his bank account. All of it went to an illegal bookie in California. The bookie was Mathew Bowyer. He says he made $16.2 million off that one customer. In the video below, Bowyer sits down with Mariana van Zeller, just out of prison, and explains how his operation worked. He was taking in about $1.5 million a month. And Las Vegas casinos knew exactly who he was. "Every casino knew what I was doing," he says. Resorts World rolled out the red carpet and hired his wife as his casino host. He and his crew lost about $24 million there. Nevada later fined Resorts World $10.5 million. In 2023, he bet $4.2 million on the Chiefs to win the Super Bowl. At halftime, Patrick Mahomes looked badly injured. The Chiefs came back and won, and Bowyer collected $4.6 million. By the time he got home, he had lost $1.5 million of it in the casino. Ohtani's interpreter got 57 months in federal prison. Bowyer got 12 months and a day. He says he now owes the government $10 million, and that his old customers owe him around $44 million he's legally not allowed to collect. Who should have stopped this first: the bookie, the casinos, or the people around Ohtani?

In 2011, Tobey Maguire paid $80,000 to settle a lawsuit over his poker winnings. He had won more than $311,000 from a hedge fund manager. The money was stolen. The manager was Bradley Ruderman. He was running a Ponzi scheme, and he lost his investors' money at the same private games Maguire played in. When Ruderman went to prison, a bankruptcy trustee sued 22 players to get it back. In the video below, UFC announcer Bruce Buffer describes what those games looked like. It was at a famous director's house in Hollywood. Everyone started with $5,000 in chips. Food, girls serving drinks, the usual. Then someone said they were changing the rules. You could buy in for whatever you wanted. "Tobey buys in for $200,000," Buffer says. Another very famous actor bought in for $75,000. So did Joe Francis from Girls Gone Wild. Buffer had brought $10,000. He lost the first $5,000 on the second hand. "I decided that game was too big," he says. "You don't want to play with money you can't afford to lose." A lot of the players at that table went on to play in Molly Bloom's game. Maguire said in court filings that he lost $168,500 to Ruderman over the years. He still had to pay back part of what he won. Should you have to return poker winnings if the other player was gambling with stolen money?

In 2009, police arrested Antoine Walker at 2 a.m. in a Lake Tahoe casino. He owed three Las Vegas casinos $1 million in gambling markers. He had earned more than $108 million in the NBA. In the video below, Walker explains how it happened. He spent six weeks training in Las Vegas that summer. "I lost a million dollars in six weeks gambling." He didn't want to pay it. "I'm trying to figure out the most creative way to get around it." While he was negotiating, the casinos went to court and got a warrant for his arrest. He was in Nevada for a celebrity golf tournament. "It's 2 in the morning, I'm drunk, I'm having a good time." Then the police walked up and asked to talk to him in the back. The original bail was set at $905,050, cash only. A judge later lowered it. In 2011, Walker pleaded guilty, got five years of probation and was ordered to pay $770,050 back to Caesars Palace, Planet Hollywood and Red Rock. He had filed for bankruptcy around the same time, so everyone assumed gambling had taken all his money. Walker says that's wrong. "I lost a million dollars gambling, but I also won a million dollars before." Would you have paid the casino right away, or tried to negotiate like Walker?

In 2008, a Las Vegas casino took Charles Barkley to court over $400,000 in unpaid gambling markers. A prosecutor said he could face a felony charge if he didn't pay. He paid. "I owe them the money," he said. In the video below, Barkley tells Shannon Sharpe what his gambling actually looked like. He played $25,000 a hand at blackjack and only took his winnings in cash. "I don't want no check. I don't want you to wire." He says he won a million dollars in a night about 7 times. He lost a million about 25 times. His friends finally sat him down. They told him his gambling wasn't out of control. "You just a f***ing idiot." He would be up $400,000 and refuse to leave, because in his head they weren't going home until he won a million. "You can never break the casino," Barkley says. "They can break you." The losses hit harder than the wins ever did. After losing a million, he says he was depressed for a week. Then the bill went to his business people, and they yelled at him until he threatened to fire them. Barkley earned more than $80 million from the NBA and endorsements. Estimates of what he lost gambling run from $10 million to $30 million. Would you have walked away up $400,000, or kept playing for the million?

In 2024, Dana White told Shannon Sharpe he beat the Palms casino for $1.6 million. Twice. Both times, they asked him to leave. He went 16 and 0 at the tables. The casino didn't ban him. It cut his limits until he couldn't bet enough to matter. In the video below, the UFC president says it keeps happening. The Mirage did the same thing. He says the Wynn is the worst on the Strip. His strategy is simple. He takes a table for himself and bets as much as he can on one hand. If he wins two or three hands at $300,000, he walks. "Let me bet as much as I possibly can." That is what casinos hate. They fly high rollers in, comp the room, and expect them to play for hours so the house edge can work. White pays for his own room and leaves when he wants. "It's me versus you. One on one." He says one of his wins in April hurt a casino's entire quarter, and they brought it up on their earnings call. His goal before he dies is to bet $1 million on a single hand. Should a casino be allowed to cut your limits just because you keep winning?

In 1992, Michael Jordan ran up a $1.2 million golf debt to a businessman named Richard Esquinas. Jordan agreed to pay $300,000. He paid $200,000 and stopped. He never stopped gambling at that level. In the video below, Cedric the Entertainer describes a night in Las Vegas with Jordan and Charles Barkley. Barkley was at the roulette table, stacking chips on every spin. Cedric was next to him with a thousand dollars. Then Jordan walked over and grabbed a stack of Barkley's chips worth about $150,000. When Barkley asked how much he took, Jordan told him it didn't matter: "I got you." Later they moved to a table where they were betting $300,000 a hand. Cedric tried to join with his $100 chips. They told him to wait for the next one. Then Cedric played golf with Jordan. He put $1,000 on every hole and lost all 18. Jordan and Barkley play for $25,000 to $30,000 a hole. "They doing billionaire sh*t," he says. Would you have kept playing after the first hole, or walked away from Michael Jordan's game?

In 2014, Dan Bilzerian won $10.8 million in one night of poker. His opponent was a billionaire who could force him to risk $18 million on a single hand. The next day, Bilzerian tweeted: "Won 10.8 million last night playing poker, headed to Puerto Vallarta to relax." Most people assumed he was lying. In the video below, Bilzerian describes the game. They were playing heads-up No-Limit Hold'em, with blinds at $10,000/$25,000. Bilzerian had $18 million on the table. The problem was his opponent. "He basically bought in for $100 million or whatever." Whatever Bilzerian had, the billionaire could cover it. "At any point, if this guy says all-in, I got to make a decision for $18 million." The billionaire's favorite move was to wait until there was $500,000 in the pot, then shove $7 or 8 million on the river. Bilzerian says the stress made his hair fall out. Then one night, with both of their girlfriends watching, the billionaire stopped looking at his cards. For an hour, he bet blind. Then he started betting Mercedes and Ferraris instead of chips. "I think he was just messing around," Bilzerian says. "He didn't care about the money." Bilzerian says that was the whole point. He never wanted to be the best player in the world. He wanted to play rich guys who weren't very good. "I didn't mind people thinking I was a rich trust fund kid. That helped me get into really good games." The pros chase titles. Bilzerian chased billionaires. Was he a great poker player, or just a great hustler?

In 2012, Phil Mickelson called his gambling partner and asked him to place a $400,000 bet on the Ryder Cup. A tournament Mickelson was about to play in. His partner was Billy Walters, the man ESPN once called the most successful gambler in the world. Walters says he refused. "I asked him if he'd lost his mind," Walters says. "Don't you know what happened to Pete Rose? You're looked at as a modern-day Arnold Palmer. I don't want any part of it." Mickelson hung up. The bet was never placed. In the video below, Walters describes his eight-year friendship with Mickelson, and how it ended. According to Walters, Mickelson placed about $1 billion in bets over the years and lost around $100 million. "He's made in excess of a billion dollars," Walters says. "He can do whatever he wants with his money." What Walters can't let go of is the trial. In 2017, Walters was convicted of insider trading and sent to federal prison. Mickelson had traded the same stock, made about $931,000 and agreed to pay it back. He was never charged. He also never testified. Walters believes that if Mickelson had told the jury what he had told the FBI, he never would have been convicted. After Walters got out, Mickelson walked up to him at a golf course and said he was glad to see him. That was the whole conversation. They haven't spoken since. Mickelson's response to the book: "I never bet on the Ryder Cup." Walters never said he did. He said Mickelson tried. Mickelson lost $100 million and kept his career. Walters kept the records. Did Mickelson owe Walters his testimony, or was staying silent his right?

In 2011, Don Johnson won $15 million from three Atlantic City casinos in six months. He didn't count cards. He didn't cheat. He just negotiated better than they did. Before he sat down, Johnson set his own terms. Bets of up to $100,000 a hand. 20% of his losses refunded once he was down $500,000. The dealer had to stand on soft 17. He could re-split aces. The casinos agreed. They wanted a whale at their tables. He took nearly $6 million from the Tropicana, $5 million from the Borgata and $4 million from Caesars. During one 12-hour session at the Tropicana, he won $1.2 million in three hands. Even with those terms, the house still had a tiny edge. In the video below, Johnson explains how he got rid of it: he brought porn stars and attractive women to the table to distract the dealers. "The more it looks like one giant party, the better it is for my side of the table," he says. "If there's a distraction, they make a mistake. What's the worst thing that can happen? I get a free bet." Caesars banned him. The Tropicana and the Borgata stopped giving him those terms. The casinos wrote the rules for a rich gambler. They didn't expect him to read them better than they did. Was it genius, or did the casinos just get greedy?

In 2012, Phil Ivey won more than $20 million from two casinos. Both refused to pay him. Ivey sued and lost. At Crockfords in London, he won £7.7 million at punto banco. At the Borgata in Atlantic City, he won $9.6 million at baccarat. He never touched the cards. His method was called edge sorting. The casino's cards had a tiny printing flaw: the pattern on one edge was slightly different from the other. Ivey's partner, Cheung Yin Sun, asked the dealer to turn certain cards around "for luck." The casino agreed. Ivey asked for the same deck, a Mandarin-speaking dealer and an automatic shuffler. The casino agreed to that too. After a few hours, Ivey could tell the high cards from the low ones just by looking at their backs. In the video below, poker legend Daniel Negreanu says the case still makes him angry: "You offered a game. I accepted. I beat you. And now you want to freeroll me? That's disgusting." Negreanu says that in his prime, Ivey would fly a private jet to casino after casino in a single night. The casinos offered him rebates on his losses. He lost at one and won at the next, and he kept the rebates. Negreanu estimates it came to about a million dollars a night. "They're giving you free drinks. Why do you think they're doing that?" he says. "You lost at your own game. Pay the piper." The courts disagreed. In 2017, the UK Supreme Court ruled that Ivey had cheated. In the US, a judge ordered him to return $10.1 million to the Borgata. The casinos chose the cards, the dealer and the rules. Ivey just looked closer than they did. Was Ivey a cheater, or did he simply beat the casinos at their own game?

Cliff Asness turned down a Goldman Sachs partnership to start his own hedge fund. Months later Goldman went public, and his old colleagues became multimillionaires overnight. His fund was losing money. Asness ran quant research at Goldman. In 1998 he left with three colleagues and launched AQR. They raised about $1 billion, reported at the time as the biggest start for a new hedge fund. The first fund opened in August 1998, the month Russia defaulted and Long-Term Capital Management began to fall apart. That wasn't the problem. The dot-com bubble was. AQR bought cheap stocks and bet against expensive ones. For 18 months, expensive kept getting more expensive. Asness calls it about the worst stretch for value investing ever. In the video below, he admits there was "more than a day" he regretted leaving. Goldman held its IPO in May 1999, while AQR kept losing. He calls that period purgatory, and says it was a little worse than that. Then the bubble burst. Today AQR manages more than $100 billion, and Forbes counts Asness as a billionaire. Was the Goldman partnership the safe choice, or the expensive one?

Before he was a billionaire, John Paul DeJoria walked into his apartment and found his toddler sitting on a pile of clothes. The note said she couldn’t handle it anymore. Their son was better off with him. Good luck. She was gone. In the video below, the founder of Patrón recalls the day he became homeless with a two-and-a-half-year-old. He was 22. He was between jobs. For three months his wife had picked up the mail, ripped up the bills and kept the money. Rent. Utilities. The bank account. He had no idea they were posted for eviction, or that the power was about to be shut off. She took their only car on the way out. Eviction was the next day. He borrowed a 1951 Cadillac that had not run in years. The water pump was broken, so he filled it with water every four hours. The car became their home. His son slept in the back seat. He slept in the front, with his head under the steering wheel, because that was the only way he could turn over at night. To eat, he walked vacant lots collecting bottles. Two cents for a small one. Five cents for a big one. He says the worst decision was pride. His mother lived in Los Angeles. His old room still had two beds. She would have taken them in. He never called. She did not find out until years later. In 1980 he and hairdresser Paul Mitchell started a company with $700. He later co-founded Patrón. In 2018 Bacardi bought it in a deal that valued the business at $5.1 billion. But in this interview he is back in that apartment, with a little change in his pocket, looking at his son and not knowing how he was going to feed him. What kind of mother leaves a toddler with a note and three months of ripped-up bills, and is there any explanation you would accept?

He turned $32,000 of rent money into $22 million, then spent years saying the check never existed. In 1995 his father had no internet and no idea what a dot-com was. Elon wanted to start a company in California. To get cash out of South Africa, Errol Musk sold a 48-foot yacht that had cost him $400,000 for $105,000, and a bush farm he says was worth $800,000 for $234,000. He told the camera he would get a third of the value, maybe a quarter. About $45,000 went out. Exchange controls and fees took a cut. By his count, roughly $32,000 arrived. Reports put it at $28,000. He says he does not know where that number comes from. Kimbal, he says, told him the money was food and rent, and that without it the brothers would not have lasted the six months they did. When Errol asked what had actually landed, he says they were too busy to tell him. Four years later Compaq bought Zip2 for $307 million. Elon’s share was $22 million. The interviewer puts the denial on the table: Elon said his father never gave him anything. Errol answers in one line. “No, I did.” After the sale they sent him $200,000. The yacht and the farm were gone. The farm, he says, would be worth $8 million now. The only record of the wire is a father on camera doing the arithmetic out loud, and a son who says the money was never there. Almost no one building a company has watched the two minutes where he prices both.

Jack Whittaker won $315 million on Christmas Day 2002. Four years later, he said he wished he had torn up the ticket. In the video below, he tells ABC's 20/20 how the money destroyed the person he loved most, his 17-year-old granddaughter Brandi. Whittaker was already rich. He ran a construction company in West Virginia and was worth over $17 million before he bought the ticket. He took the lump sum, about $113 million after taxes. He gave tens of millions away, built churches, and started a charity. He gave Brandi $2,000 a week and bought her four cars. She was 17. The money brought new friends, then drugs. Her boyfriend died of an overdose in one of Whittaker's houses in September 2004. Three months later, Brandi was found dead, wrapped in a plastic sheet behind a junked van. He was robbed of $545,000 in cash from his car. He said he faced more than 400 legal claims. "I don't like Jack Whittaker," he says at the end. "I just don't like what I've become." Would you still take the $315 million?

In July 1973, the richest man on earth was handed a $17 million ransom note for his 16-year-old grandson. J. Paul Getty was worth about $2 billion. He would not pay a penny. Eight days after John Paul Getty III vanished in Rome, his mother sat in front of the cameras and asked the kidnappers, through the press, to make contact again. That exchange is the video below. She never said the family would pay. A reporter heard it that way anyway. She cut him off: “No, I didn’t say the family is ready to pay. I said the family is ready to negotiate.” She chose that word because the money was not hers to promise. Getty had already told the press he had 14 other grandchildren, and if he paid for one, he would soon have 14 kidnapped grandchildren. Months went by. The kidnappers cut off the boy’s right ear, mailed it to an Italian newspaper with a lock of his hair, and warned that the other ear would follow. Only then did Getty move. The demand was bargained down to about $2.9 million. He put up $2.2 million, the maximum his lawyers said he could deduct, and loaned the rest to his own son at 4 percent interest. Five months after the abduction, the boy was released. Years later he said he never asked his mother why the money took so long. “What’s the use?” Watch her again. She never promised payment. She couldn’t. The richest man in the world was still pricing his grandson’s ear. Was that the only way to keep the other 14 alive, or did a tax deduction matter more than the boy in the cave?

Stanley Druckenmiller bought Nvidia without knowing the earnings. Three months earlier, he says, he could not even spell the name. He has told the story more than once. In the video below, he walks through the trade that still bothers him. In early 2022 his younger partners started talking about AI. Then he noticed the kids at Stanford drifting off crypto and toward it. He had used that signal before. Palantir, in 2008, was the company every smart kid wanted to join. His partner brought a room of AI people into Palo Alto. Most of it went over his head. He still knew it was big. He asked one question. What should I buy? The answer was Nvidia. He put on a position small enough to matter, not big enough to define the fund. Two weeks later ChatGPT launched. He doubled. On a Morgan Stanley macro call, a tech analyst told the rates crowd they were staring at trees and missing the forest. He doubled again. By December 2022, on an investor call, he brushed off the whole macro debate. Rates did not matter. The only thing that mattered was AI and Nvidia. The stock ran from about 150 to 390. He said in public he could not see himself selling for two or three years. Then it hit 800. He sold. Five weeks later it was 1,400. He was sick. The man in the room who knew ten times more about AI had already sold his. Druckenmiller, who could not quote the earnings, had held longer, and still got out too soon. He said he is not used to making six times his money in an equity in two years. And he is not Warren Buffett. Would you have sold at 800, or is that the exact moment the trade gets hard? Save the video to hear him finish it, and follow for the trades the best investors still regret.