15 Athletes Who Made a Fortune—Then Lost It All
A shocking look at superstar athletes who made millions—only to lose it all through bad investments, lavish spending, and financial mismanagement.
- Alyana Aguja
- 5 min read
Most of them become stars and millionaires overnight, earning millions from contracts, endorsements, and championships—only to see it all vanish. From lavish expenditures on luxury lifestyles to failed investments and run-ins with the law, these money meltdowns are a cautionary tale for anyone who inherits a sudden windfall. Some are able to rebuild their lives, while others are stuck in the vicious cycle of financial collapse, illustrating that it’s easy to make money—but easy doesn’t always make it stay.
1. Mike Tyson (Boxing)
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At one time, the world’s heavyweight champion, Mike Tyson, accumulated over $400 million in the ring. However, careless spending, legal issues, and an extravagant lifestyle—with pet tigers as part of the package—had him bankrupted by 2003. He then regained ground with acting, public speaking, and a successful podcast.
2. Allen Iverson (Basketball)
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The electrifying NBA player made approximately $200 million in contracts and endorsements but had trouble with bad financial choices and lavish spending. He was famously said to have only $1,000 in his bank account, even though he used to be rich. Luckily, a trust fund from his Reebok contract guarantees he’ll receive a $32 million payment when he’s 55.
3. Evander Holyfield (Boxing)
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The ex-heavyweight champion earned more than $250 million but lost it on unsuccessful business deals, payments of child support to 11 children, and an enormous 54,000-square-foot mansion. His house was eventually repossessed, and he was forced to sell memorabilia to settle debts. Holyfield subsequently earned a living in promotional appearances and mentorship schemes.
4. Antoine Walker (Basketball)
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Though he made $108 million during his NBA career, Walker filed for bankruptcy two years after retiring. Excessive spending, poor investments, and gambling losses depleted his wealth. He later became a proponent of financial literacy, cautioning young players about the misuse of money.
5. Lenny Dykstra (Baseball)
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The one-time MLB All-Star earned millions on and off the field but lost it all in a string of bad investments and legal issues. He declared bankruptcy in 2009, stating he had just $50,000 in assets but was more than $30 million in debt. Dykstra also spent time in prison for fraud and money laundering.
6. Boris Becker (Tennis)
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The German tennis great won six Grand Slam championships and made over $50 million, but bad money choices resulted in bankruptcy in 2017. Bankrupting himself through failed business deals and an expensive divorce made him lose his wealth. In 2022, he was even imprisoned for concealing assets in his bankruptcy case.
7. Vince Young (Football)
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Once a star NFL quarterback, Young earned $35 million in salary alone but blew it on high-end cars, parties, and even purchasing an entire flight’s worth of seats. His poor money management and bad investments saw him become bankrupt by 2014. He has since been employed as a coach and analyst to reform his life.
8. Darren McCarty (Hockey)
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The four-time Stanley Cup winner with the Detroit Red Wings made millions but spent all on booze, gambling, and poor business ventures. He filed for bankruptcy in 2006 and then struggled with addiction. After getting sober, he stabilized himself in sports media and public speaking.
9. Sheryl Swoopes (Basketball)
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The WNBA legend earned millions as the first-ever female basketball player to have a signature Nike shoe but went bankrupt in 2004. She had poor financial choices, such as investing her money in the wrong people. She later resurrected her career as a coach and mentor.
10. Jose Canseco (Baseball)
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A baseball legend with a reputation for home runs and a scandalous career, Canseco earned more than $45 million but lost it through poor investments, lawsuits, and extravagance. His financial woes compelled him to work on reality TV, boxing bouts, and even selling his championship ring. He is still a social media icon and author of books.
11. Terrell Owens (Football)
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Although he earned approximately $80 million during his NFL career, Owens lost his wealth due to lavish expenditures, poor financial advisors, and child support payments. He eventually turned to reality TV and semi-pro football to earn a living. Owens then began a podcast and speaking engagements to survive.
12. Dennis Rodman (Basketball)
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The flamboyant basketball player made over $27 million but wasted it on partying, business failures, and legal troubles. His child support obligations at one time totaled more than $800,000, resulting in financial ruin. Rodman now earns a living from appearances, endorsements, and his unusual diplomatic connections with North Korea.
13. John Daly (Golf)
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A two-time major champion, Daly earned millions but lost more than $50 million to gambling alone. His heavy living, which included heavy drinking and partying, only made his financial situation worse. He eventually resorted to selling merchandise, music albums, and endorsements to keep himself afloat.
14. Marion Jones (Track and Field)
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Formerly the planet’s fastest woman, Jones amassed millions of endorsement dollars before her career unraveled when she fell into a doping scandal. Sentenced to jail time for lying under oath, she faced serious financial difficulties and was forced to sell off her medals and possessions. Later, she secured stability by playing professional basketball and talking about redemption.
15. Scottie Pippen (Basketball)
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Though he earned more than $100 million during his time in the NBA, Pippen lost most of it due to poor investments, such as a $4 million private jet that never flew. He was also victimized by poor management by advisors. Although not quite destitute, he returned to media and business pursuits in order to continue amassing his wealth.