High Roller Files

Dan Bilzerian was about to put $2 million on Floyd Mayweather. The CEO of Aria personally approved the bet. He never placed it. May 2015. Mayweather vs Pacquiao. Dan went to the fight. A bet that size wasn't normally allowed. So he called Bobby Baldwin, who ran Aria. "He approved it." He was literally going to go do it. Then one thought stopped him. "If Mayweather loses this fight, he gets a billion dollars." His math: Lose the fight, still take $150 million plus pay-per-view. Guaranteed rematch, another $250 million. Win the third one, God knows. "Best case scenario for this guy is he actually loses the fight." One loss on the record. Beats the guy twice. Still the champ. "And now he's worth over a billion dollars." Mayweather won on points. Dan read the fighter right and talked himself out of the bet.

Kevin Plank took Under Armour's last $2,000 to Atlantic City to make payroll. He lost it all. He already owed around $40,000 across 5 credit cards. Payroll was short. He needed to turn $2,000 into $4,500, so he got in his car and drove to the casino. He got up to about $4,000. Then lost everything. On the way home, he couldn't even pay the toll at the Delaware Memorial Bridge. Traffic stopped while someone came out to write down his details. He remembers crying in his car, telling himself he'd blown it and chosen the wrong business. Then he checked his P.O. box. Inside was a $7,800 check from Georgia Tech. His reaction: "What was I talking about? Back in business. Let's go get this thing."

Tim Tebow was offered $1 million for 1 day of work. Bill Belichick asked him to turn it down. 2013. Tebow had just landed with the Patriots. "I don't think it was even a contract. I'm just trying to make the team." Then a company offered him a $1 million endorsement deal. One day of work, on an off day. But when he joined, Belichick had asked him to stay under the radar. "I said, yes sir, I'll do my best." So he called the coach about the offer. "I'd really appreciate it if you turned it down." He turned it down. A few days later the Patriots cut him. No job. No car. No home. "That day of service would have been twice as much as I would have made if I would have made the team for the entire season." He passed on $1 million for a 1% better shot at a backup job. He didn't get the job.

Ray Romano was getting almost $2 million an episode. He wanted to quit a season early. Everybody Loves Raymond. 9 seasons. 210 episodes. 12 Emmys. The money on the table: close to $2 million per episode, plus the back end and syndication. He and Phil Rosenthal wanted out after season 8. "You don't want to be the guy who keeps playing baseball because he can hit 6 homers a year instead of 35." "We weren't motivated for financial reasons. This was our baby." So they made a deal with themselves. Find 8 fresh ideas they were proud of, stretch them to 16 episodes, then stop. They found 8. They did 16. They walked. "I don't think Phil and I regret one second." Then the bubble popped. A couple of months later he crashed. Within 3 months he was seeing his therapist twice a week. He walked away from almost $2 million an episode. The reruns reportedly still pay him up to $18 million a year.

Stephen A. Smith said no to almost $2 million a year from ESPN. A year later, he was out. He had his own show. People screamed his name on the street. The offer: a little under $2 million a year, for 3 years. He looked at what his colleagues were making and said no. He thought the talks would keep going. They shut down. His airtime shrank. Then ESPN let him go. No income. Living off his savings. "Believing that I would never be allowed back to ESPN." What would he change? "I would have taken a deal." "Because of people screaming my name... I thought that equated to dollars." He did get back. By 2012 he was on First Take. In 2025, ESPN gave him a 5-year deal reported at $100 million. So was saying no the best thing that ever happened to him? "Possibly. But it was a very, very tough time."

Chad Johnson made millions in the NFL. Asked how he's doing financially, he said: "I've been broke since '78." He was born in 1978. 6-time Pro Bowler. Still says athletes don't have money. "The people signing a check have a fortune." His idea of rich looked nothing like the other guys'. On Hard Knocks, he went shopping at Claire's. "My jewelry has always been fake." Rolexes. Diamonds. "It all shines the same when the light hits it." The Ferrari, the Lamborghini and the Phantom? "All of which were bought with TV money." No house here. No house there. No bottles at the club. No entourage. His first 2 years in the league, he slept at the stadium. Best money lesson he ever learned? "Save it, period."

John Daly lost $55 million gambling. He only found out the number from his own tax records. Two-time major champion. He never kept count. When he wrote his book, he and his co-writer went through every return. He guessed 20, maybe 25 million. It came out to 55 to 57. How is that even possible? "Stupidity." 1991 to 2007. About $3.2 million a year, for 16 years. His sessions had no clock. Slots for two days straight. Blackjack for a day and a half in one sitting. "The only time I'd get up is to go to the bathroom." He'd take $1, $2, $3 million markers. Play 7 hands at $15,000 to $20,000 each. He's been up $4 or $5 million and walked out down $2 million. "Because I wouldn't get up." Does he regret it? "I had a lot of fun doing it."

Barry Sternlicht got fired at 30. His wife was pregnant with their first kid. Today he's worth billions. He grew up selling tadpoles for 10 cents each. Then knives door to door. The dream was simple: "I wanted a pool and a tennis court." He left Harvard Business School $88,000 in debt. Wall Street wouldn't hire him. A Chicago real estate firm did. He sat next to the founder at every negotiation. Bears games with Walter Payton. Bulls games with Michael Jordan. Then 1991 hit. The firm was close to bankruptcy and needed to cut overhead. "They told me I lost my job. I was 30 years old." "I'm like, I'll take a job for $50,000. I need a job." Then a guy he barely knew offered to back him in his own firm. That firm became Starwood. Westin, Sheraton, W Hotels. The kid who wanted a pool and a tennis court now runs a firm with over $100 billion in assets.

Magic Johnson turned down Nike stock at 19. By his own math it would be worth $1.5 billion today. He had just won the national championship. He had just beaten Larry Bird. Every shoe company came to sign him. Converse offered the most money. "When you're Black and you're broke, you take the most money." Then Phil Knight walked in with a different offer. "I can't offer you the same amount of money as Converse, but I can give you something called stock." Magic didn't know what stock was. He passed. 46 years later he did the math. "A billion five." He says he only understood the mistake when Michael Jordan came out with Air Jordan. "That's when I knew I could have owned some of that." So he learned what equity was. Movie theaters. 125 Starbucks. Stakes in the Dodgers and the Lakers. Today he's a billionaire. "God put me in a position to make up for it. I'm doing OK."

Charles Barkley has lost $1 million in a single day somewhere between 10 and 20 times. By his own count. He's won a million in a day maybe five or six. He can't give an exact number. It goes back to the 80s. "Do you think it's ever gotten out of hand?" "Yeah, no question it got out of hand." He quit for about two years. Then one night his friends told him something he didn't expect. "Gambling's not your problem. You're just an idiot." They had been at the table with him. He'd be up $300,000. $400,000. $500,000. $600,000. $700,000. They'd say let's quit. He wouldn't. He had to get to a million. So they gave him a rule. Up $50,000 or a couple hundred thousand, you cash out and go have fun. "You can't break the casino." He says gambling has been a lot more fun since.

The owners of the UFC once asked Dana White what they could sell it for. His answer was $6 to $8 million. 12 years later it sold for $4 billion. In 2001 the Fertitta brothers bought it for $2 million. Then they kept paying. Another $44 million went in. "That's one hell of a hobby." The lowest point was a phone call. Lorenzo Fertitta told Dana he couldn't keep funding it. He couldn't call his brother again to ask for more. "I need you to get out there and see what we can get for this thing." Dana made calls all day. That night he gave him the number. "I don't know, man. Six, maybe eight million." They were already 30-something million in the hole. It was Dana's idea to buy it in the first place. "I just lost my friends 30-something million bucks." Lorenzo said he'd call him tomorrow. The next day he did. "Let's do it. Let's keep going."

Arnold Schwarzenegger was a millionaire before Hollywood ever paid him. Not from movies. From apartments. He came to America with almost nothing. He saved every dollar from bodybuilding seminars, posing exhibitions and a small mail order business. "I remember when I had $26,000 or whatever it was, in cash in the bank. And I was looking around like a fanatic for an apartment building." He bought a 6 unit building for $235,000 to $240,000 and lived in the owner's unit. Two or three years later he sold it for double. "I had the courage to do it, to take all my money, down to the last dollar, and put it into this investment. And that's what I always did." Then a hundred plus apartments. Then offices on Main Street in Santa Monica. "Before I ever got heavily into the film business, I already was a millionaire." Conan, Terminator, all of it came after.

George Foreman lost the last fight of his career. The same night his lawyer handed him a $1 million check. Not for boxing. For a grill. A friend told him he was making all the brands in his commercials wealthy. Get your own product. "How much are you going to pay me?" "We're not going to pay you." They found a grill. George didn't want to use it. His wife insisted. "She said, it works, George." He asked for 16 of them. One for his mom, his aunt, his cousin, the rest for his training camps. That was the whole plan. The first check was $1,500. The next one was $15,000. Then the grill sold over $100 million. At one point the checks were $5 million a month. In 1999 Salton paid $137.5 million just for his name. November 1997, Atlantic City. He loses his last fight. The crowd boos, everyone says he was robbed. His attorney walks up with a $1 million royalty check. "I said, that's not what we call being robbed."

John Paul DeJoria was promised $500,000 to start a company. He got $700. 1980. He and hairdresser Paul Mitchell split it 30/30. The other 40% went to an investor putting in half a million dollars. Paul flew in from Hawaii, out of money. Then a friend told JP the backer had pulled out. "He never invested a dime in it." Inflation was 12.5%. The prime rate was 17%. "The lowest point was telling Paul." He asked Paul how much money he had in his pocket. "Well, I could afford an extra 350 bucks, JP." JP had a couple hundred dollars and a car he could stay in on Mulholland Drive. So he went to his mom. "Mom, can I borrow $350?" $350 from Paul. $350 from his mom. That was the company. For two years they couldn't pay their bills on time. Paul Mitchell grew into a billion-dollar-a-year brand. DeJoria later co-founded Patrón, sold for $5.1 billion. Watch 0:41. A future billionaire asking his mom for $350.

Ray Dalio built the biggest hedge fund in the world. In 1982 he had to borrow $4,000 from his dad to take care of his family. He started Bridgewater in 1975. Seven years later he was sure a crash was coming. He calculated that American banks had lent emerging countries about 250% of their bank capital. Money those countries were never going to pay back. He went on Wall Street Week. He testified to Congress. In August 1982, Mexico defaulted. It looked like he was right. "And I couldn't have been more wrong. That was the exact bottom of the stock market when Mexico defaulted." He let all 8 of his people go. He lost his own money and his clients' money. "I had to borrow $4,000 from my dad because I didn't have really enough money even to take care of my family at that point." He calls it probably the most valuable thing that happened in his life. It made him start asking one question: "How do I know I'm right?"

Ted Turner was worth $7-8 billion. After the AOL merger, he told CNN you can get by on "a billion or two" if you economize. In 1996 he merged Turner Broadcasting, the home of CNN, into Time Warner for $7.5 billion in stock. He owned about 10% of the combined company. "I thought that I was buying Time Warner, not selling to them." Then came AOL. The 2000 merger diluted him from 10% to 3%, and the stock collapsed with the dot-com crash. In 2002 AOL Time Warner posted a $99 billion loss, the biggest annual loss in US corporate history. Asked if it was the biggest regret of his life, he said Time Warner was a very good company "before AOL was put into it, then it was toxic." Once his stake was diluted, management came after him. He lost his job at the company he built. In 2012 he summed it up on CNN: "I lost my job here. I lost my fortune, most of it. Had a billion or two left. You can get by on that if you economize."

Mike Tyson made around $300 million in the ring. By 2003 he was bankrupt and about $23 million in debt. Mansions, Bengal tigers, an entourage on payroll. Then it was gone. Years later he was asked what happened. His answer is not what you'd expect: "Aside from me having a lot of fun, I allowed people to be involved with my life that really wasn't honest people." "And that was my fault. I should have paid more attention to my business." No bitterness. He says when he was making $30-40 million a fight, he couldn't get anything done. "I was a megalomaniac back then." Now he calls going broke "probably the best thing that ever happened to me." Watch 0:42. That's the part nobody expects from Mike Tyson.

In 2022, Sam Bankman-Fried was worth $26 billion. Three weeks after FTX collapsed, he joined the New York Times DealBook Summit and was asked about his money. "I've had a bad month." Then he said the quiet part: "I don't have any hidden funds here. Everything I have, I'm disclosing. I think I have one working credit card left. I think it might be $100,000 or something like that." "I'd put everything I had into FTX." FTX was valued at $32 billion at its peak. It filed for bankruptcy in November 2022, and billions in customer money were missing. A year later, a jury found him guilty on all 7 counts. He got 25 years. From $26 billion to one credit card in under a month.