Back in Time Today
Sports stars often reach dizzying heights of fame and fortune, becoming heroes to millions. But the spotlight can fade quickly, leaving some athletes facing financial ruin, legal troubles, or personal demons.
These 17 sports legends once had it all – money, fame, and success – before watching their empires crumble in dramatic fashion.
1. Mike Tyson: Boxing’s Youngest Champion Knocked Out by Debt
The fearsome ‘Iron Mike’ became the youngest heavyweight champion in history at just 20 years old. His lightning-fast knockouts and intimidating presence earned him over $300 million during his career. Unfortunately, Tyson’s spending habits were as explosive as his punches. Exotic pets (including infamous tigers), mansions, and a massive entourage drained his fortune. Legal troubles and a prison sentence further damaged his finances. By 2003, Tyson declared bankruptcy, owing $23 million in debt. Though he’s rebuilt some stability through acting, cannabis ventures, and exhibition fights, his journey represents one of boxing’s most dramatic financial collapses.
2. Allen Iverson: NBA Star Who Crossed Over into Financial Trouble
Basketball’s most electrifying guard earned over $200 million during his NBA career. Known for his crossover dribble and fearless playing style despite his 6-foot frame, ‘The Answer’ was cultural royalty in the early 2000s. Maintaining a 50-person entourage and lavish spending habits, Iverson burned through cash at an alarming rate. Reports claim he would travel with dozens of suitcases, buying new clothes rather than doing laundry. By 2012, an infamous photo showed him begging outside a mall—though later debunked, it symbolized his fall. Thankfully, a Reebok trust fund worth $32 million becomes accessible when he turns 55, providing a financial safety net.
3. Antoine Walker: From NBA Millions to Bankruptcy in Record Time
The Boston Celtics star and three-time All-Star earned approximately $108 million during his NBA career. Walker’s signature ‘shimmy’ celebration became iconic as he helped lead the Miami Heat to a championship in 2006. His downfall came from supporting 70 friends and family members, maintaining multiple luxury homes, and gambling losses. The real estate market crash of 2008 delivered the knockout blow to his already fragile finances. Walker filed for bankruptcy in 2010, listing assets of $4.3 million against debts of $12.7 million. He has since rebuilt his life as a financial advisor and ESPN analyst, using his painful experience to educate young athletes about money management.
4. Evander Holyfield: The Real Deal’s Fortune Takes a Real Hit
The only four-time heavyweight champion earned over $230 million during his legendary boxing career. Holyfield’s courage in the ring was unmatched, famously continuing to fight Mike Tyson even after having part of his ear bitten off. Child support for his 11 children from multiple relationships created massive financial strain. His 54,000-square-foot Georgia mansion with 109 rooms symbolized his excessive spending before being foreclosed on and sold for just $7.5 million. By 2008, Holyfield was broke despite his enormous career earnings. He was even forced to sell his Olympic bronze medal and championship belts at auction. His cautionary tale highlights how quickly athletic fortunes can disappear without proper financial guidance.
5. Lenny Dykstra: Baseball Star’s Post-Career Crash and Burn
The scrappy centerfielder nicknamed ‘Nails’ helped the New York Mets win the 1986 World Series. After baseball, Dykstra initially found success as a businessman, creating a luxury car wash chain and a magazine for professional athletes. His empire collapsed during the 2008 financial crisis. Dykstra’s attempt to flip Wayne Gretzky’s $17.5 million mansion backfired spectacularly, leading to bankruptcy in 2009 with just $50,000 in assets against $31 million in debts. Legal troubles followed, including grand theft auto charges and financial fraud. Dykstra served prison time and was even homeless briefly, living in his car. His dramatic fall represents one of baseball’s most shocking post-career implosions.
6. Johnny Unitas: Football Legend’s Late-Life Financial Fumble
The Baltimore Colts quarterback revolutionized the passing game and won three NFL championships. His crew cut and black high-top cleats symbolized football’s golden age as he set records that stood for decades. Unlike many athletes who squandered fortunes on luxuries, Unitas lost his money through failed business ventures. His bowling alley chain and restaurant investments drained his savings, while a Florida real estate development project delivered the final blow. The football icon declared bankruptcy in 1991 at age 58. Adding insult to injury, Unitas later sold his NFL championship rings and memorabilia to survive financially. His story reminds us that even careful investment, without proper guidance, can lead to financial disaster.
7. JaMarcus Russell: The NFL’s Most Expensive Draft Bust
Selected first overall in the 2007 NFL Draft, Russell signed a rookie contract worth $68 million with $32 million guaranteed. His cannon arm and physical tools made him seem like a can’t-miss quarterback prospect for the Oakland Raiders. Weight issues, work ethic concerns, and poor performance led to his release after just three seasons. Russell completed only 52.1% of his passes and won only seven games as a starter, making him one of football’s most notorious draft busts. Financial troubles followed his NFL exit. In 2011, his Oakland mansion faced foreclosure proceedings. Russell attempted multiple NFL comebacks but never played another professional snap. He earned approximately $39 million for just 31 games—about $1.2 million per appearance.
8. Terrell Owens: Hall of Fame Talent, Hall of Shame Finances
The flamboyant wide receiver amassed over 15,000 receiving yards and 153 touchdowns during his 15-year NFL career. Despite Hall of Fame statistics, T.O.’s confrontational personality and touchdown celebrations often overshadowed his on-field brilliance. Child support for his four children reportedly cost him $44,600 monthly, creating massive financial strain. Bad investments and excessive spending drained his estimated $80 million career earnings at an alarming rate. By 2012, Owens admitted he was broke during an appearance on Dr. Phil. He later missed child support payments and faced foreclosure on multiple properties. Though he’s partially recovered through entrepreneurial ventures, his financial collapse serves as a warning about the dangers of poor money management.
9. Kenny Anderson: NBA Point Guard Who Lost His Direction
The New Jersey Nets selected Anderson second overall in the 1991 NBA Draft after his standout career at Georgia Tech. His smooth ball-handling and court vision earned him an All-Star selection and approximately $63 million over 14 NBA seasons. Supporting seven children from five different women created enormous financial pressure. Anderson’s lavish spending included owning eight luxury cars simultaneously, including two Mercedes and two Range Rovers. By 2005, he filed for bankruptcy despite his substantial career earnings. Anderson has since rebuilt his life as a basketball coach and motivational speaker. He survived a 2019 stroke and now emphasizes financial education for young athletes, turning his painful experience into valuable lessons for others.
10. Scottie Pippen: Jordan’s Sidekick Shortchanged Himself
The six-time NBA champion and Hall of Famer formed half of basketball’s most famous duo alongside Michael Jordan. Ironically, Pippen’s financial troubles stem partly from being underpaid during his prime years with the Chicago Bulls. Pippen signed a seven-year, $18 million contract extension in 1991 that became one of sports’ most notorious underpayments. While this wasn’t his only financial misstep, it set the stage for later troubles. Poor investments followed, including a $4 million private jet that required an additional $1 million in repairs before it could fly. Pippen also lost millions in bad real estate deals and through a financial advisor who mismanaged his money, proving that even basketball IQ doesn’t guarantee financial wisdom.
11. Dorothy Hamill: Olympic Gold Medalist’s Financial Thin Ice
America’s sweetheart captured Olympic gold in figure skating at the 1976 Innsbruck Games. Her signature ‘Hamill camel’ spin and wedge haircut became national sensations, leading to lucrative endorsement deals and professional skating opportunities. Hamill’s financial troubles began when she purchased the financially troubled Ice Capades franchise in the early 1990s. The touring ice show had been declining in popularity for years, and her investment quickly turned disastrous. She filed for bankruptcy in 1996, listing $1.3 million in assets against approximately $1.6 million in debts. Unlike many athletes who lost fortunes to lavish spending, Hamill’s financial downfall came from an ambitious business venture and poor investment timing. She has since rebuilt her finances through skating shows, books, and speaking engagements.
12. Vince Young: Texas Legend’s Fortune Fumbled Away
The electrifying quarterback led the University of Texas to a national championship before being selected third overall in the 2006 NFL Draft. Young signed a rookie contract worth $58 million, including $26 million guaranteed with the Tennessee Titans. His spending habits quickly became legendary for all the wrong reasons. Young reportedly spent $5,000 weekly at The Cheesecake Factory and once purchased nearly every seat on a Southwest Airlines flight for privacy. By 2012, he was broke despite earning approximately $34 million in NFL salary alone. Young filed for bankruptcy in 2014, listing assets between $500,000-$1 million against debts between $1-10 million. His financial collapse was so complete that he even had to auction off his college football awards.
13. Michael Vick: Quarterback’s Career and Fortune Gone to the Dogs
The first overall pick in the 2001 NFL Draft revolutionized the quarterback position with his dual-threat abilities. Vick signed contracts worth over $130 million during his career, including a $100 million deal with the Philadelphia Eagles in 2011. His empire collapsed in 2007 when he was convicted for his involvement in a dogfighting operation. The scandal cost him nearly two years in federal prison and approximately $142 million in lost salary, endorsements, and legal fees. Vick filed for bankruptcy in 2008 with $16 million in assets against $20 million in debts. Unlike many on this list, he engineered a remarkable comeback, returning to the NFL and repaying his creditors. His story represents both a cautionary tale and an example of financial redemption.
14. Dennis Rodman: Rebounding King Who Couldn’t Rebound Financially
The eccentric defensive specialist won five NBA championships with the Detroit Pistons and Chicago Bulls. Known for his rainbow-colored hair, body piercings, and unmatched rebounding ability, Rodman earned approximately $27 million during his NBA career. His flamboyant lifestyle, including lavish parties and excessive drinking, drained his finances rapidly. Child support obligations created additional financial pressure, with Rodman reportedly owing over $800,000 in back payments at one point. By 2012, Rodman’s attorneys claimed he was broke and unable to pay child support. His financial struggles have continued despite occasional income from reality TV appearances and his unusual friendship with North Korean leader Kim Jong Un. The rebounding machine’s inability to secure his financial future remains one of basketball’s most colorful cautionary tales.
15. Boris Becker: Tennis Champion Served with Bankruptcy
The German tennis prodigy became Wimbledon’s youngest champion at just 17 years old in 1985. Becker’s powerful serve and diving volleys earned him six Grand Slam titles and approximately $25 million in prize money during his career. His financial troubles stemmed from a costly divorce, failed businesses, and tax issues in multiple countries. A particularly expensive paternity scandal resulted from a brief encounter in a London restaurant broom closet, costing him millions in support payments. Becker was declared bankrupt in 2017 over an unpaid loan of more than £3 million. In 2022, his situation worsened when he received a 2.5-year prison sentence for hiding assets during bankruptcy proceedings. The tennis legend’s fall represents one of the most dramatic financial collapses in sports history.
16. Mark Brunell: NFL Quarterback Sacked by Bad Investments
The left-handed quarterback enjoyed a 19-year NFL career, earning three Pro Bowl selections and a Super Bowl ring as Drew Brees’ backup. Brunell earned approximately $50 million during his playing days, primarily with the Jacksonville Jaguars. His financial downfall came through failed business ventures rather than lavish spending. Brunell invested heavily in nine Whataburger franchise locations and various real estate developments that collapsed during the 2008 financial crisis. He filed for bankruptcy in 2010, listing $5.5 million in assets against $24.7 million in debts. Brunell has since rebuilt his life as a high school football coach and sports broadcaster. His story highlights how even seemingly safe investments can lead to financial ruin without proper diversification and expert guidance.
17. Jose Canseco: Baseball’s Bad Boy Strikes Out Financially
The muscular outfielder became MLB’s first 40-40 player (40 home runs and 40 stolen bases in a single season) in 1988. Canseco earned approximately $45 million during his 17-year baseball career, winning two World Series championships. His financial troubles began with his 1999 divorce from Jessica Canseco, which reportedly cost him millions. Poor investments, including a failed sports complex in California, further drained his baseball fortune. Canseco filed for bankruptcy in 2012, listing less than $21,000 in assets against nearly $1.7 million in debts. His post-baseball career has included celebrity boxing matches and controversial tell-all books about steroid use in baseball. The slugger who once seemed larger than life has struggled to maintain financial stability since leaving the game.