High Roller Files

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.

Shaq once turned down Howard Schultz and his own Starbucks stores with one sentence. Schultz wanted him to open Starbucks locations in Black neighborhoods. Shaq grew up on sweet tea and hot chocolate. He had never seen anyone in his family drink coffee. So he looked Schultz in the face and told him it wouldn't work. In the video below he explains exactly what he said, and who took the deal right after him. "On every corner, in every city, in every country, I see a Starbucks."

Donald Trump once mailed John McEnroe a letter offering $1 million to play Serena or Venus Williams. McEnroe said no. He was calling a match when the envelope showed up. "Dear John, I want to offer you $1 million to play either Serena or Venus." Serena and Venus had been saying they could beat a lot of guys. Somehow McEnroe became the one everybody asked. He was the number one player in the world. He wasn't going to sit there and say he couldn't beat them. So why turn down $1 million? In the video below he explains exactly why. Then he asks a question about the NBA that nobody else gets asked. "Somehow it's me, the old fart."

Vince Young signed an NFL deal worth up to $58 million. Less than 8 years later he filed for bankruptcy, and a lender was coming for his Rose Bowl rings. $25.7 million of that rookie deal was guaranteed. The lender said he took out a high-interest $1.9 million loan. Vince says the money never hit any of his accounts. They got a judgment against him anyway. Rose Bowl rings, trophies, cars, the house, all on the table. "You never took a dime from the person... but you suing me. It was painful." Filing for bankruptcy was embarrassing, he says, mostly because of "me being who I am." His uncle was part of the team around him back then. "It's my dad's brother, so I definitely thought that he had my back a little bit more." Asked if he'd do anything differently with the money, he says no. If his mom needs $1,000, she gets $1,000, and he goes to work to put it back in the account. What he learned: "Definitely don't sign a power of attorney." "Sign your own checks."

Bob Costas got his father's entire estate in an envelope at the wake: $6,000 in $100 bills, collected from a bookie. His dad didn't bet at casinos or the track. He bet on ballgames. The mortgage literally rode on the outcome. Bob liked watching the games with him. When the Christmas money was going down the drain and his mom and sister fled, he stayed. "At his best, if he was flush with cash, he was very, very generous." May 15, 1970. Bob is 18. A cop knocks, looks past him and tells his mother to sit down. Heart attack, walking through JFK Airport. Sunday at the wake, a gambling buddy named Steve Collins hands Bob a thick envelope. "Your father was up when he died. Give this to your mother." A bookie will never pay a dead man. So Steve went to the bookie and said "John sent me to collect." $6,000. All in $100 bills. "That was my father's entire estate." Bob went on to call the Olympics for NBC. His father never saw or heard any of it. "I'll never know."

Terrell Owens made north of $50 million in the NFL. Then he saw the true state of his finances. 8 years in San Francisco. Then a new contract with the Eagles. It was around 2004, 2005. He was switching agents. "I did not have the financial security that I thought I had." How big was the gap between what he thought he had and what he really had? "I think it was a considerable difference." He puts it on himself first: "Not being smart enough, responsible enough to be on top of my financial situation." He also trusted the people around him. They looked his brothers and sisters in the eyes, and he felt they had his best interests at heart. A lot of people say he's broke. "I have money. If you want to look at me and say I'm broke and famous, that's cool." "I wouldn't say I'm broke. Maybe in a financial bind."

Henry Winkler's father took his bar mitzvah money and never paid it back. Henry now jokes his kids will inherit $350. He was 13. The family lived above its means. His father kept a summer home an hour outside New York City. Henry put the cash and the bonds in the bank. Then his father came to him. "I need your bar mitzvah money." "Will you pay me back?" His father said he didn't have to. "After everything I've given you." "It was my gift for my 13th birthday." Decades of success later, the Fonz still calls money "the bane of my existence." "Money makes me crazy. You always think you're going to run out." "There is no connective tissue between the reality and what I live in my head." His kids were told there will be no inheritance. Henry says he has no idea where that came from. "I believe that there will be at least $350 left. And then you guys can just divide that amongst yourselves."

Matthew McConaughey was offered $14.5 million for one rom-com. He said no. He was the go-to rom-com guy. Easy movies, fun movies, good money, high demand. The catch: nobody would even consider him for a serious role. "If I can't do what I want to do, I'm going to stop doing what I've been doing." So he called his agent. No more rom-coms. The first 6 months, nothing came in but rom-coms. Some big offers. One came in at $14.5 million. "I said no." Then nothing. No offers at all. Nobody mentioned his name for another 14, 15 months. There were moments he thought he'd have to find another career. "I didn't want out. I just wanted in in a different way." About 20 months in, the calls came back. The Lincoln Lawyer. Killer Joe. Magic Mike. True Detective. Dallas Buyers Club. Dallas Buyers Club won him the Oscar. The $14.5 million he turned down was the price of the ticket.

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."

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."

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.

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.