It’s easy to think that a multimillion-dollar sports career means financial security forever. But for some of the most famous names in athletics, fortune faded fast thanks to overspending, risky investments, and money mismanagement.
From championship parades to bankruptcy filings, these 15 athletes are proof that even the biggest paychecks can’t protect you from financial free fall. Whether it was trusting the wrong people or living far beyond their means, their fortunes disappeared in spectacular fashion.
15. Mike Tyson
At his peak, Tyson earned hundreds of millions — and burned through it just as quickly. Lavish mansions, exotic pets, and costly divorces drained his bank account, leading to a high-profile bankruptcy in the early 2000s.
14. Lenny Dykstra
Known as “Nails” during his gritty MLB career, Dykstra’s post-baseball business ventures ended in disaster. Bankruptcy, jail time, and a string of scandals left his finances in worse shape than his teeth.
13. Marion Jones
Once America’s track and field sweetheart, Jones’ career imploded after a doping scandal and prison time. Legal bills and poor money moves left her reputation — and her bank account — in ruins.
12. Curt Schilling
A World Series hero on the mound, Schilling poured his fortune into a video game company that collapsed. The failed gamble brought lawsuits, debt, and a harsh lesson in high-stakes business.
11. Vince Young
The former NFL QB signed massive contracts, but extravagant spending — including famously dropping thousands at Cheesecake Factory — quickly caught up to him. Bankruptcy followed.
10. Dorothy Hamill
The Olympic skating icon’s graceful spins didn’t protect her from financial collapse. A failed business and money mismanagement pushed her into bankruptcy in the ’90s.
9. Antoine Walker
Walker earned over $100 million in the NBA, but bad real estate bets, an oversized entourage, and unchecked spending left him broke just a few years after retiring.
8. Evander Holyfield
Even with career earnings most fighters only dream of, Holyfield’s lavish lifestyle — and his 109-room mansion — eventually proved unsustainable. Foreclosure and debt followed.
7. John Daly
A fan favorite for his larger-than-life personality, Daly’s financial life was just as extreme. He reportedly lost tens of millions to gambling, wiping out much of his tour earnings.
6. Allen Iverson
One of the most electrifying players in NBA history, Iverson’s lavish lifestyle and poor planning nearly left him penniless — until a trust fund set up during his career kept him afloat.
5. Mark Brunell
The steady NFL quarterback made big investments in real estate and franchises, but the 2008 market crash sank them all. Bankruptcy soon followed.
4. Dennis Rodman
Rodman’s colorful persona extended to his spending habits. With back taxes, child support, and nonstop partying, his finances eventually crumbled.
3. Sheryl Swoopes
A pioneer of the WNBA, Swoopes was a superstar on the court but faced money trouble off it. Business missteps and debt led to a bankruptcy filing.
2. Diego Maradona
A global soccer legend, Maradona battled massive tax bills and reckless spending for much of his life, adding financial chaos to his already dramatic career.
1. Scottie Pippen
Despite six NBA titles and tens of millions in earnings, Pippen fell prey to bad investments and shady financial advice. Court fights over lost money became an unexpected chapter in his Hall of Fame story.
