Kyrex

T-Pain rented his Bugatti to DJ Khaled for $3,000. It ended up in a music video where it looked like someone else's car. That was the end of the friendship. The song was Ace Hood's "Bugatti." The Bugatti in the video was T-Pain's. He waited for someone to say so. Nobody did. "It was just like, yep, cool car." So he said it himself. "That's my car. DJ Khaled paid me three grand to use my car." Khaled called him. "That's what you're doing?" T-Pain said they made it look like the car was theirs. Khaled told him to watch the video again. "Okay, you didn't say it. But okay." Then the ask. "Take it back. Take the post down." "I kind of still stand by what I said." The post didn't come down. One more problem. The photo he posted to call them out showed Khaled's own artist, Ace Hood. "You just used my artist in the smear campaign." "I don't know what you're talking about." His summary, years later: "This is why me and Khaled, to this day, don't f*** with each other."

Dave Portnoy sold Barstool Sports for over half a billion dollars. Then he bought it back for $1. Shannon Sharpe can't get past it. "How the hell do you sell a company for over a half a bill and then buy it back for a buck?" "It's one of the great trades of all time." Better than the Louisiana Purchase, he says. The buyer was a gambling company. Gambling needs licenses. Portnoy is not a guy state regulators love. "I'm a controversial guy." Barstool was losing money. Penn wanted out. So, $1. Why not $100 million? "I wouldn't pay 100 million for it." Barstool without him, he says, doesn't work. "I would have paid $100." Shannon reads the history back to him. $15 million for 51%. $163 million for 36%. $388 million for 100%. Then $1 for all of it. He says he'll never sell again. There's a catch in the deal: if he does, Penn gets half. "Now, if you want to write me a check for a billion..." "I never say never."

Dr. Cheyenne Bryant told Shannon Sharpe she will never sign a prenup. Then she described the one she'd want him to sign. Shannon asks where she stands. "I'm not signing a prenup." "Why?" "Well, why would I?" Shannon has a story for that. He used to ask his broke friends if they had one. "So when you leave, you keep all your nothing." His rule is simple. What he had before her, she doesn't get. She has a different plan. First clause: if he cheats. "This is the amount that will be paid out. And it's not going to be pennies." Why so big? "So that my heartbreak don't also feel broken in my pockets." Second clause: everything else gets written down. $20 million in property? Then the paper says exactly how much of it is hers. "It's going to be lined out clear on what I'm agreeing to." When splitting comes up: "No, no, no, no, no. I'm not splitting." And the one prenup she'd walk away from: "There will be no prenup that says if we divorce, you get nothing. We don't marry."

Bobby Brown once decided to spend $1 million in a single day. He pulled it off. Three watches, two cars and a house. Shannon Sharpe reads it off his card and stops. "Hold on. It says you spent a million dollars in one day." "In one day." "What the hell you buy?" "I bought three watches, two cars, and a house." "You didn't want to space it out?" "I wanted to spend a million dollars in one day. I mean, just for the hell of it." Shannon asks if he thought it would work like Brewster's Millions. Spend one, get ten. "I wish that was the case." Does he see it now? "Yeah, I do. I do." He told his wife the story. She laughed. "We got to work then." His advice today is the opposite of that day. Save. Invest. Buy land, because "they're not making anymore." Does he ever look back at all of it? "If I could switch that around, I'd be the cheapest mother on the planet."

Aaron Carter said he made over $200 million before he turned 18. At 18, he found out he owed millions in taxes his parents never paid. Years later, on national TV, he said: "I'm good, but I'm not great." He was a teen idol before he was a teenager. His parents ran his money. By law, 15% was supposed to go into an account for him. What he says he got at 18: about $2 million. And a tax bill. 2013. He files for bankruptcy. More than $3.5 million in debt. $1.3 million of it from taxes on what he earned at 16. 2019. The Doctors. He's 31, in recovery, and the headlines are about him again. "I'm good, but I'm not great." "And I never will be great, when it comes to my recovery." He reads the comments out loud. Strangers asking if he's overdosed yet. "What did I ever do to deserve that?" He talks about rehab. His family didn't come. "Nick didn't come, my mom didn't come, nobody came." His brother tweeted that he was there if Aaron needed help. They lived 3 hours apart. "Come see your brother." He knew how it would look. "I don't care."

Annie Knight was earning $60,000 a year in marketing and couldn't see how she'd ever afford a house. Five years later, she says she has made $6 million. Her dad found out when a Daily Mail reporter knocked on his door at 6 a.m. His first question was about the money. It started in lockdown. "It was boring. I was earning about $60,000 Australian dollars a year." She wanted a house one day. "How am I going to do that with this money?" So she opened an OnlyFans on the side. A couple of grand a month, saved for a deposit. Two years in, her employer found out. She was fired. She took it as a sign. Early 2022, she went full-time. Then she went viral. Her mom saw it in a Channel 7 article on Facebook. Her dad got the reporter at the door. Then he called her. "Is it true you're earning this amount of money per month?" "Yeah." "Fair enough. I'd probably do it, too." 13 years at a private Catholic girls' school. A marketing degree. A $60,000 salary. Now, in her words: "I'm financially free."

Fat Joe says he wired his accountant the money for his taxes. The accountant never paid. Fat Joe went to prison and came out "dead broke." He'd done everything wrong as a kid in the Bronx. Robbed people. Sold drugs. Then he went legit. And trusted the wrong guy. "An accountant f*cked me and didn't pay my taxes while I was sending them wire transfers." His lawyer showed the feds the wires. It didn't matter. "You as the leader of your household is responsible for whoever you hire." June 2013. A judge in Newark gives him 4 months. More than $3.3 million in income with no tax returns filed. $718,038 owed. "They took all my money, millions of dollars from me, and left me dead broke." Rich friends lined up with offers. A million here, a duffel bag of cash there. He said no to all of it. "I never borrowed money from nobody." So he took every show that paid. Yugoslavia. Africa. China. Poland. "Wherever you name that had a dollar attached to the bottom of the table, I was out there." In court, he said it differently. "It was my responsibility."

Michael Irvin got a $1 million signing check from the Dallas Cowboys. He didn't cash it. He left it on the table so everyone who walked in could see it. He came from Fort Lauderdale. He calls it Brokeville. "I was young, too, man. I was crazy." First, the house. He picked it for one reason: an 8-foot gate. "All I knew is I don't want nobody to see me in the pool." Then the check. "That million dollar check. I left that right there on the table." His financial people kept calling. Every day it sat there, he was losing money. "I'm winning. What you talking about?" Why leave it out? Because of where he came from. "I was getting $20 a weekend and mom took the first 15." $5 a weekend. Then $1 million on the table. And a big family waiting on it. Mom. Brothers. Sisters. Shannon Sharpe puts it plainly: "There ain't a whole lot left over." It took Irvin that whole first contract to learn the lesson. "Making money is one thing. How you let it go is as important."

Björn Borg won Wimbledon five years in a row. In 2006 he put all five trophies up for auction. July 1978. He has just beaten Jimmy Connors in the final. He's 22. How good was it? "I think probably was maybe one of my best matches I ever played." "Because it was the most important match for me in my life." "I had a lot of pressure." A year later he becomes the first player to earn over $1 million in prize money in a single season. At 26 he walks away from tennis. He launches a fashion brand with a friend. Luggage, sportswear, aftershave. In 1989 it goes bankrupt. 1997. Eleven creditors want more than $1 million. Friends help him avoid bankruptcy. 2006. He tells the auction house he's selling for "financial security." Years later, another version: "It wasn't a money thing, not at all." Then the phone calls start. John McEnroe, the man he beat in the 1980 final, calls him again and again. Borg buys the trophies back. His line about all of it: "The most disappointing thing was that people abused me."

T-Pain bought a $1.7 million Bugatti. Then his accountants called. They might have to sell his house. He had told them to send the money for the car. "When I bought that Bugatti, that was the last bit of my money and I had no idea." The call came after. "Hey, so we may have to sell your house." "What are you talking about? I have a Bugatti." That money was supposed to finish paying off the house. "My house is paid for." "Uh, yeah, not anymore." Was anyone watching the money? "I never knew what the hell was going on with my finances." People were stealing from him. He didn't care. "I should still have enough." Then his granddad pitched a business. Pants with the boxers already sagging out. He put in $150,000. "I didn't have it, but I gave it to him." The pants never got made. Years later, Balenciaga sold the same idea. Today, if $4 leaves one of his accounts, his phone alerts him. Back then, $1.7 million left without him noticing. "I had so much money that it was just like, why would I care?"

Martin Shkreli paid $2 million for the only copy of a Wu-Tang Clan album. On camera, he joked the Feds might end up owning it. They did. Late 2015. His Midtown apartment. A VICE reporter, a bottle of wine, a chess game. A few months earlier he raised the price of an HIV drug from $13.50 a pill to $750. Is he evil? "I think I'm the opposite of evil." His view of the business is simple. Companies have owners. "Their owners demand that they extract as much profit as possible." "That's the way the world works." Then the album. Two CDs in an embossed case in his living room. Will anyone ever hear it? "I could see myself in a place where I break it." Snap it in half. Bury the pieces. "I just bought it a few months ago, and I was arrested a month ago." 2017. A jury convicts him of securities fraud. 7 years. The government seizes the album to pay what he owes. He bought it so nobody else could have it. "Who knows, maybe the Feds will own it soon."

Vince Young's mother told him he'd end up dead, crippled or in jail. He ended up with a $58 million NFL contract. Then bankruptcy. Houston. Middle school. A big fight after spring break. The police pick him out of the crowd and put him in handcuffs. His mom comes to get him. In the car, she's screaming. "You're going to end up dead, crippled or in jail." He looked around and saw she was right. Friends shot. Friends in and out of prison. "I didn't want to fall into that bunch. Be that stat." At home there was fighting. So he climbed out his bedroom window and sat in a tree. What did he think about up there? "Why is our family fighting all the time?" He knew the answer. "It was because we was broke." 2006. The Titans draft him third. $58 million, about $26 million guaranteed. 2012. He's out of the league. His lawyer: "Vince needs a job." 2014. Bankruptcy. The boy in the tree knew what broke does to a family. The man with $26 million guaranteed ended up there anyway. "It always goes back to not having income."

Michael Vick signed the biggest contract in NFL history. $130 million. From a federal prison cell, he handed $8 million to a financial adviser who turned out to be a med school graduate. 2007. Dogfighting. 23 months in federal prison. He says the hardest part wasn't the cell. "The toughest part was being in there and filing bankruptcy." He couldn't believe it. "I just gave eight million dollars to this guy over here. I'm not filing bankruptcy." He filed anyway. $16 million in assets. Over $20 million in debts. The Falcons wanted their signing bonus back. "I respect them for that." He had admitted in court he never balanced a checkbook or reconciled a bank statement. Inside, he made a promise. "I'm gonna make full restitution to everybody." He played again. And by 2017 he had paid back $17.4 million of the $17.6 million he owed. His reason was simple. If he paid everyone back, maybe the $8 million would come back too. "A lot of money came up missing." He paid back every creditor. Nobody paid him back. "Where's the rest of it?"

$80 million in the NFL. Two years after his last game, Terrell Owens told Dr. Phil he couldn't afford his child support. May 2012. Three of the four mothers of his kids are in the studio. One of them says they never needed a judge. "I never took Terrell to court ever." He says he kept raising her payments himself. "6,000 to 8 to 10 to 12 on my own." Then she found out another mother was getting $20,000. She hired a lawyer. "So I had to start paying her 20." Dr. Phil cuts to it. Can you afford all this? "Not at this moment in time, no I can't." She says he spent the money on fighting her in court instead. His answer to all three: "The only time any of you really have picked up the phone is because of money." The cars? The houses? "Well I did, and those were investment properties." "You're not going to see me popping bottles in the club." At his peak he paid about $45,000 a month. $80 million earned. Not enough for four kids. "It wasn't a plan."

Burt Reynolds was once the biggest box office star in Hollywood. At 79, his proof that he wasn't broke was a red tie. 2015. His Florida home. A TV crew asks him to set the record straight. "I'm not bankrupt. If I was bankrupt, I wouldn't have my red tie on." At his peak he made $10 million a year. Then came the restaurants. Po' Folks. Daisy's Diner. Both failed. $20 million gone, and he had signed for it personally. 1996. Chapter 11. His second wife, Loni Anderson? He says she maxed out a $45,000 credit card in half an hour. "She liked to spend money. Mine." "I really couldn't afford her." He turned down Han Solo, James Bond and Pretty Woman. Which one does he regret most? "All of those. I wish I had done them all." His advice: "Watch out who your friends are." In the '80s he was worth an estimated $200 million. When he died in 2018, about $500,000. Would he marry again? "No, ma'am." "Check, please."

Boris Becker won Wimbledon at 17 and made about $50 million on court. On the day he was sentenced, he wore a tie in Wimbledon's purple and green. April 29, 2022. London. "To make a matter even more dramatic, it was the birthday of my wife." Flowers in the morning. Then court. "There was a 50/50 chance I got a suspended sentence." His lawyers told him: "Get ready. You might have to go inside." He had been declared bankrupt in 2017. After that, he moved hundreds of thousands of pounds to other accounts, including his ex-wife's. The rent on his Wimbledon house was £22,000 a month. The sentence: 30 months. That night he became prisoner A2923EV. "Those numbers I'll never forget." Wandsworth didn't care who he was. "I was one of many." How did it start? Wimbledon at 17. Again at 18. "Everybody wanted a piece of me." At 17 he won Wimbledon unseeded. At 54 he was a number. "I'm a human being. I make mistakes."

Gary Coleman made about $18 million as a child star. When his trust was opened at 18, his parents' share was $770,000. His was $220,000. 1978. Diff'rent Strokes. He's 10, with failing kidneys. His parents set up the trust. Then they put themselves on the payroll of his production company. 1989. He's 21. His mother asks a court to take control of his $6 million fortune. She says he can't handle his affairs. His answer: "Obviously stems from her frustration at not being able to control my life." That same year he sues his parents and his business manager. $3.8 million. They deny all of it. 1993. A judge awards him $1.28 million. Taxes, lawyers and dialysis take most of it. That year, on TV: "If someone had told me... I would've got out." 1999. He files for bankruptcy. He takes a job as a security guard. He never speaks to his parents again. May 2010. He dies at 42. His mother tells People: "We loved Gary very much." They managed his money for 18 years. They hadn't heard his voice in over 10. "I'm sick of all of you people."

Jack Whittaker won $315M on Christmas 2002. He gave his 17-year-old granddaughter $2,000 a week and 4 cars. He was already a millionaire. His construction business was worth $17M. In the video below, he is asked whether 4 cars made sense for a teenager. "To a young kid cars mean a lot, and I'm very proud that she had four cars." Her name was Brandi. He calls her the shining star of his life. "She was very responsible with her money." Her boyfriend, Jesse Tribble, starts showing up in new clothes. His father notices. "I know firsthand she bought things for Jesse." Soon they are both on drugs. "Papa, all I care about is drugs." Jack checks her into 3 treatment programs. None of them work. September 2003. Jesse is found dead of an overdose in an empty house Jack owns. His father: "I blame her for my son's death." December 2004. Brandi disappears. On December 20, she is found dead behind a junked van. The cause of death is listed as unknown. "I really had my arms around her and protected her before I won the lottery." He could buy her 4 cars. He couldn't get her through 3 treatment programs. His wife said she wished she had torn the ticket up. "I wish that we had torn the ticket up too." Then he says this about himself. "I don't like Jack Whittaker."

Archie Karas turned $50 into $40M in Las Vegas. It took him almost 3 years. Losing it took 3 weeks. December 1992. He has just lost his whole bankroll at poker. He gets in his car with $50 in his wallet and drives to Vegas. First, pool. One man keeps raising the stakes. $40,000 a game. Karas walks away with $1.2M. Then poker. He beats Chip Reese. Only Johnny Chan beats him in a first round, for $900,000. Then dice, because dice are faster. "I ended up winning every $5,000 chip at Binion's Horseshoe." By 1995 he is up more than $40M. "Money means nothing to me." Then the 3 weeks. Craps: $11M. Back to Chip Reese: $2M. Baccarat: $17M. Total: $30M. He goes home to Greece, comes back, and bets $300,000 a roll until it is gone. Years later, he is asked how much he won in total. "I lost the money back anyway." "I consider myself the king of gamblers." Asked what he was most proud of in his life: "Not much, to tell you the truth." He died in 2024, at 73. $50 to $40M took almost 3 years. $40M back to nothing took 3 weeks.