10 Athletes Who Had It All, Then Lost It
Some sports legends have gone from the thrill of victory to the shock of financial ruin. Despite earning millions, these athletes lost their fortunes due to poor decisions, bad investments, or unexpected challenges. Their stories prove that financial literacy and smart money management are just as important as talent in professional sports.
Leon Spinks
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Winning the heavyweight title against Muhammad Ali should have set Leon Spinks up for life. Sadly, money slipped through his hands as fast as his boxing reflexes once were. Bad addiction decisions, low-paying jobs, and mounting medical bills left him broke. In his later years, he relied on Social Security and the generosity of fans to get by.
Roland “Rollie” Fingers
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Rollie Fingers had a signature with his iconic mustache, but that couldn’t keep his bank account full. His fortune vanished after failed investments in pistachio farms and Arabian horses. Despite making millions in baseball, he ended up bankrupt and struggling to recover financially after watching his business ventures completely fall apart.
Sheryl Swoopes
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WNBA superstar Sheryl Swoopes dominated the court but couldn’t control her finances. Bad investments and business failures drained her wealth and ultimately forced her to file for bankruptcy in 2004. She once was the face of women’s basketball and even earned lucrative endorsements, including the signature Nike Air Swoopes. Financial mismanagement left her scrambling to rebuild her life.
Johnny Unitas
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Every quarterback in the modern NFL owes something to Johnny Unitas, but football greatness didn’t protect him from financial ruin. A series of disastrous business ventures, including a failed circuit board company, left him in serious debt. Medical expenses made things worse, and by the end of his life, one of football’s greatest players had little left to show financially.
Bradley Wiggins
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Britain celebrated Sir Bradley Wiggins as a Tour de France hero without realizing his financial struggles after retirement would tell a different story. Tax disputes and legal troubles chipped away at his fortune and left him far from the comfortable life expected of an Olympic and cycling champion.
Dorothy Hamill
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America’s sweetheart on ice went from Olympic glory to unexpected financial struggles. Believing she was making a smart business move, Dorothy Hamill purchased the Ice Capades, but it quickly became a disaster. The company went bankrupt, and so did she. Her gold medal remained priceless, but her fortune was gone after one massive investment mistake and extravagant spending.
Boris Becker
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Wimbledon crowned Boris Becker a teenage tennis king at 17. That fete was dethroned spectacularly by bad financial decisions. A high-profile tax evasion case and a costly divorce led to his bankruptcy. Things got even worse by 2022 when he ended up behind bars for hiding assets. A UK judge terminated his bankruptcy case in 2024.
OJ Simpson
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Legal troubles and financial collapse defined OJ Simpson’s post-football life more than his NFL career ever did. His multimillion-dollar fortune disappeared through endless legal battles, including a civil suit that left him owing millions. His assets were seized, and after serving time for an unrelated robbery, he had lost everything.
Marion Jones
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Marion Jones sprinted to Olympic stardom, but her fall from grace came just as fast. After admitting to doping, she was stripped of her medals, lost endorsement deals, and even served time in prison. Financial ruin followed, forcing her to sell her home and start over from scratch.
Dennis Rodman
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Few NBA players lived a more outrageous lifestyle than Dennis Rodman, but the party eventually ended. Unpaid child support, legal fees, and reckless spending drained his fortune and left him in serious financial trouble. Despite making millions in basketball, his over-the-top lifestyle and poor money management turned him from a larger-than-life icon into someone struggling to stay afloat.
Lenny Dykstra
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Having been a fearless competitor on the field, Lenny Dykstra took the same aggressive approach to business—and failed miserably. He threw money into investments that collapsed, racked up debt, and eventually ended up in legal trouble for fraud. Bankruptcy forced him to give up everything, and a once-promising financial future turned into a cautionary tale of reckless decision-making.
Diego Maradona
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Diego Maradona’s talent made him a soccer god, but his ineptness in finance management never matched his legendary status. Extravagant spending, tax evasion, and bad financial choices left him owing millions. Italian authorities chased him for years over unpaid taxes, and by the time he passed away, his once-massive fortune had dwindled.
Darren McCarty
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Fighting was Darren McCarty’s specialty on the ice, but financial troubles delivered a knockout blow after retirement. Gambling debts, a costly divorce, and bad investments left him with nothing. Forced to auction off prized possessions, including his Stanley Cup rings, he had to rebuild from the ground up. Antoine Walker
Spending came easy for Antoine Walker, but keeping his fortune didn’t. Despite earning over $100 million in the NBA, he lost it all to reckless purchases, gambling, and an ugly separation. By 2010, he had to file for bankruptcy and start from scratch.
Andre Rison
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Andre Rison’s big contracts and endorsement deals made a rich man during his NFL career. However, excessive spending made sure that money didn’t last. He splurged on luxury items, racked up debt, and failed to pay child support, which led to bankruptcy. The flash and glamour of his playing days disappeared, and he learned the hard way that millions don’t last forever.
Allen Iverson
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Allen Iverson was once the face of the NBA, with a killer crossover and a $200 million fortune to match. But bad financial decisions, a costly divorce, and a lavish lifestyle drained his wealth fast. Despite massive endorsement deals, including a lifetime contract with Reebok, he found himself struggling to pay bills. At one point, he reportedly couldn’t afford a cheeseburger. Thankfully, a trust fund from Reebok helped keep him afloat, but his financial downfall was a hard lesson in excess.
Kerry Wood
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Blazing fastballs and record-breaking strikeouts should have secured a legendary career, but injuries had other plans. Kerry Wood’s rookie season hinted at Hall of Fame greatness, especially after his unforgettable 20-strikeout game. But arm troubles turned dominance into disappointment, forcing him into a bullpen role before an early retirement. While he didn’t lose everything, the fortune and fame he once seemed destined for never fully materialized. His story became a reminder that raw talent isn’t always enough to outrun lousy luck.
Vince Young
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Vince Young’s NFL career peaked with a thrilling Rookie of the Year win and a memorable run to the playoffs. But after fame, things quickly unraveled. Poor financial decisions, including lavish spending and failed investments, drained his fortune. By 2014, he filed for bankruptcy, struggling with debts and unemployment. The former superstar still grapples with financial hardship as of 2025.
Latrell Sprewell
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Latrell Sprewell was once an NBA star, known for his scoring ability and fiery passion on the court. But after turning down a $21 million contract extension, things spiraled. Financial mismanagement, along with a series of personal issues, led to bankruptcy. The lavish lifestyle he once enjoyed faded, and by 2015, Latrell was struggling with debts, a sharp contrast to his high-flying career.