Big Wins, Bigger Losses

Ever looked at your bank app after a weekend out and thought, “Where did it all go?” Now imagine that—only with millions at stake. That’s what happened to some of the world’s most talented athletes. Lavish cars, bad deals, and hangers-on drained their accounts faster than their highlight reels went viral. It’s oddly relatable, just on a much grander scale. So, let’s take a look at 20 athletes who turned record-breaking victories into financial wipeouts.

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1. Mike Tyson

Mike Tyson once earned over $400 million through boxing purses and endorsements, but his fortune quickly vanished through reckless spending, legal troubles, and poor financial choices. Extravagant mansions and even pet Bengal tigers drained his wealth, forcing him to declare bankruptcy in 2003.

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2. Vince Young

Once hailed as one of the NFL’s brightest stars, Vince Young saw his fortune disappear faster than his fame. Despite earning over $25 million, lavish spending, poor investments, and failed ventures left him financially ruined, leading to his 2014 bankruptcy with debts exceeding $1 million.

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3. Diego Maradona

The tale of Diego Maradona serves as a sobering reminder that athletic genius doesn't guarantee financial wisdom. That’s because with Argentina's 1986 World Cup victory, he evaporated millions through reckless spending and a crushing $37 million Italian tax burden.

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4. John Daly

Known for his larger-than-life persona on and off the golf course, John Daly’s wealth vanished through self-destructive habits. He earned millions during his career, yet lost nearly $50 million to gambling, faced multiple expensive divorces, and accumulated alcohol-related debts that led to bankruptcy.

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5. Dennis Rodman

Dennis Rodman’s journey from NBA glory to financial ruin was spectacular in scale. His $27 million career earnings dwindled through heavy gambling, costly divorces, and disastrous money management. The final blow came when financial advisor Peggy Ann Fulford embezzled his funds, purchasing luxury goods under his name and leaving him broke.

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6. Sheryl Swoopes

Sheryl Swoopes, the first player ever signed to the WNBA and a three-time MVP, achieved iconic status with her own Nike shoe, the Air Swoopes. Yet poor financial decisions eroded her fortune, leading her to file for bankruptcy in 2004.

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7. O.J. Simpson

Once celebrated as both an NFL legend and Hollywood celebrity, O.J. Simpson’s riches couldn’t withstand his turbulent personal life. Massive legal expenses and a $33.5 million civil judgment consumed his earnings, slashing his net worth from $10.8 million in 1992 to roughly $3 million by 2024.

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8. Leon Spinks

What began as boxing's ultimate Cinderella story—Spinks dethroning Muhammad Ali for the heavyweight crown after just eight pro fights—crumbled into a stark lesson in fortune's fragility. The champion's wealth evaporated, leaving him to sweep YMCA floors in Nebraska and, at his lowest, without a home.

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9. Dorothy Hamill

Dorothy Hamill twirled her way into America’s heart with Olympic gold in 1976 and sparked a national craze with her famous “wedge” haircut. But the ice got slippery off the rink—her skating ventures melted her fortune, forcing the beloved star to file for bankruptcy in 1996.

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10. Lawrence Taylor

Few athletes lived as boldly as Lawrence Taylor, the New York Giants’ fearless linebacker and two-time Super Bowl champion. His millions vanished through wild spending and disastrous ventures, turning his post-football life—including a short Hollywood career—into a cautionary tale that ended in bankruptcy.

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11. Darren McCarty

Darren McCarty’s story proves even champions can lose big off the ice. The four-time Stanley Cup winner with the Detroit Red Wings saw his fortune collapse under gambling debts, costly divorces, and failed ventures, leading him to file for bankruptcy in 2006 with more than $6 million owed.

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12. Travis Henry

While Travis Henry was building an eight-season NFL career and banking $11 million as a running back, he was simultaneously crafting a rather different legacy. His professional path ended in a substance abuse suspension, while his personal choices led to jail, resulting in over $170,000 in annual support payments.

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13. John Arne Riise

At the height of his career, John Arne Riise was conquering Europe with Liverpool’s 2005 Champions League win, yet trouble brewed off the pitch. His business ventures spiraled into chaos, and by 2007, the Norwegian star—still earning top-tier wages—was forced to declare bankruptcy.

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14. Lenny Dykstra

Bankruptcy hit Lenny Dykstra hard in 2009 after his high-flying real estate empire came crashing down. Once a World Series champion with the 1986 New York Mets and nicknamed “Nails” for his toughness, Dykstra’s ventures—including car washes—crumbled under debt, wiping out the millions he’d earned.

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15. Johnny Unitas

From gridiron god to business blooper, Johnny Unitas proved that even 18 seasons of NFL brilliance and three MVP awards couldn't quarterback a successful enterprise. That’s because his post-football business ventures spiraled into a spectacular 1991 bankruptcy featuring a whopping $3.2 million debt to creditors.

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16. Allen Iverson

Allen Iverson hit financial rock bottom in 2012 after filing for bankruptcy over a $900,000 jewelry debt. Known for his lavish habits—like buying a car after losing one—he now lives off an $800,000 annual Reebok deal and awaits a $32 million trust payout in 2030.

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17. Deuce McAllister

Once a hometown hero in New Orleans, Deuce McAllister powered his way into franchise history as the Saints’ all-time leading rusher. Yet his post-football ventures proved disastrous—his Nissan dealership’s collapse in 2009 forced him into personal bankruptcy, erasing much of his hard-earned NFL wealth.

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18. Mark Brunell

While Mark Brunell's NFL journey sparkled with three Pro Bowl selections and a famous Super Bowl ring with the Saints, his financial playbook proved far less successful. The star quarterback's $50 million in career earnings evaporated through misguided real estate and restaurant ventures.

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19. Warren Sapp

In a masterclass of how not to manage millions, NFL legend Warren Sapp turned his business playbook into a fumble of epic proportions. The Hall of Fame defender's failed ventures, coupled with mounting alimony and child support debts, took his $59 million fortune straight into bankruptcy court by 2012.

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20. Evander Holyfield

Evander Holyfield’s financial downfall became as legendary as his boxing career. The former heavyweight champion earned over $200 million in the ring, but lavish spending, poor investments, and massive financial obligations—including mansion foreclosure—drained his fortune.

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