Millions earned, millions lost. In the high-stakes world of professional sports, even the most prominent stars can see fortunes slip through their fingers. These athletes once reigned at the top, but their lavish lifestyles, bad investments, and costly mistakes ruined their riches. Here’s a look at those who soared and then fell—spectacularly.
Mike Tyson
Despite being one of the greatest boxers in history, Mike Tyson’s extravagant lifestyle caught up with him. He earned over $300 million during his career but filed for bankruptcy in 2003. Lavish spending, statutory issues, and bad fiscal planning drained his assets. Today, Tyson has recovered somewhat through business ventures and entertainment appearances.
Evander Holyfield
Evander Holyfield, a boxing legend with countless victories, saw his $250 million fortune dwindle due to costly monetary choices. Maintaining his 109-room mansion and meeting child support obligations drained his net worth. By 2012, the mansion was sold in foreclosure, leaving Holyfield grappling with significant debt and fiscal challenges.
Antoine Walker
Two years after retiring from the NBA, Antoine Walker filed for bankruptcy in 2010. Known for lavish spending, such as buying multiple luxury cars and indulging in high-stakes gambling, he blew through his $108 million career earnings. His real estate investments, which collapsed during the 2008 recession, worsened his financial troubles. Now, Walker focuses on educating athletes about managing wealth.
Vince Young
Once a star quarterback for the Tennessee Titans, Vince Young saw his $34 million revenue disappear quickly. Known for splurging $5,000 weekly at the Cheesecake Factory and buying out a 120-seat flight to fly solo, he filed for bankruptcy in 2014. Financial missteps and extravagant choices left him struggling with debt.
Allen Iverson
A costly lifestyle and divorce took a heavy toll on Allen Iverson’s fortune, which had surpassed $200 million during his NBA career. In 2012, a judge ordered his bank account seized after he failed to pay $860,000 owed to a jeweler. Fortunately, a Reebok trust fund of $32 million awaits him in 2030 when he turns 55.
Lenny Dykstra
The end of Lenny Dykstra’s baseball career marked the beginning of a significant decline in his life. His once-thriving car wash empire collapsed under poor management, and involvement in unethical activities led to severe consequences. Accusations of unlawful behavior stripped away his net worth and tarnished his reputation. What was once a life of success and accolades ended in financial ruin.
Sheryl Swoopes
Often called the “female Michael Jordan,” Sheryl Swoopes dominated the WNBA but struggled financially after her professional journey ended. Earning $50 million through basketball and endorsements, including a Nike deal, didn’t prevent her from filing for bankruptcy in 2004. Ineffective money management and failed business ventures left the Hall of Famer facing severe monetary challenges after her incredible on-court success.
Curt Schilling
A former MLB World Series champion, Curt Schilling watched his financial empire collapse after his video game company, 38 Studios, failed in 2012. He poured millions into the business, only to lose over $50 million when it all fell apart. Schilling later admitted that nearly all his net worth vanished due to the venture.
Warren Sapp
NFL legend Warren Sapp filed for bankruptcy in 2012 despite earning over $80 million throughout his career. Overspending, ongoing child support obligations, and poor investment decisions gradually drained his finances. Sapp’s bankruptcy case revealed that he had lost nearly all his assets, including his Super Bowl ring and property.
Terrell Owens
Terrell Owens faced severe economic difficulties during his post-NFL years after earning over $80 million. By 2012, misguided money management, child support, and failed investments overwhelmed him with debt. Owens later admitted in interviews that placing trust in the wrong people and mismanaging his earnings were critical factors in his downfall.
Michael Vick
During his prime, Michael Vick ranked among the NFL’s highest-paid players, securing a $130 million contract. However, his involvement in a dogfighting scandal caused severe financial and personal consequences. Following his time away, Vick made an impressive return with the Philadelphia Eagles, focusing on rebuilding his finances and reputation.
Scottie Pippen
A celebrated NBA player, Scottie Pippen, saw much of his $120 million earnings evaporate due to bad economic decisions. In one devastating instance, he lost $20 million in a failed investment deal. Bad advice and risky ventures hindered his financial recovery, leaving him struggling to secure what remained of his hard-earned wealth.
Dorothy Hamill
Olympic gold medalist Dorothy Hamill captured the hearts of millions with her graceful skating. Earning substantial income from her skating career didn’t prevent Hamill from filing for bankruptcy in 1996, driven by unsuccessful holdings and the monetary strain of running the Ice Capades. Her ability to rebuild her life despite such challenges inspires countless people.
Darren McCarty
Former Detroit Red Wings star Darren McCarty won four Stanley Cups but lost millions due to gambling, unwise investments, and divorce. By 2006, McCarty filed for bankruptcy, squandering the riches he earned in his NHL career. He later admitted that his off-ice issues significantly contributed to his financial collapse.
Andre Rison
Andre Rison, a former NFL wide receiver, amassed around $20 million during his professional journey but struggled to hold onto his fortune. With over $1 million in unpaid child support, Rison’s financial situation grew even worse, fueled by his penchant for expensive cars and homes. By 2007, he filed for bankruptcy, losing much of his wealth to poor decisions and ongoing disputes.
15 Athletes Who Squandered Their Fortunes