Athletes Who Went Broke Immediately After Retiring

Many professional athletes struggle to adjust to life after sports, even after earning large sums of money. Poor financial decisions and lavish lifestyles often lead to financial hardship, with legal problems and the expenses of maintaining luxury properties quickly draining their savings. Without a continuing income, career earnings can disappear rapidly. This list showcases some famous athletes who faced significant financial difficulties after retirement.

Mike Tyson

Okay, so everyone knows Mike Tyson was a hugely successful boxer, raking in tons of money during his prime. But it’s pretty shocking to learn he filed for bankruptcy back in 2003. It wasn’t a lack of earnings, though – it was how he spent it. We’re talking serious money blown on things like jewelry and fancy cars. On top of that, he was saddled with massive legal bills and owed a ton in taxes. A big group of people he supported and some really bad investments just made things worse. Thankfully, he managed to turn things around, finding success later on through acting and making personal appearances. It’s a wild story, honestly.

Evander Holyfield

Evander Holyfield, once worth half a billion dollars, lost his fortune due to child support and unsuccessful investments. He lost his large Georgia home to foreclosure in 2012 and struggled with poor financial advice and expensive living. To pay off debts, he had to sell prized boxing items and championship belts. Today, Holyfield continues to work on sponsorships and partnerships to manage his remaining finances.

Allen Iverson

Despite earning over $150 million during his NBA career, Allen Iverson struggled financially after retiring. He generously supported a large circle of friends and family with lavish gifts, and his spending consistently outpaced his income towards the end of his playing days. He famously admitted to a judge that he couldn’t even afford a cheeseburger. Fortunately, a trust fund established through a shoe deal will eventually provide him with millions when he turns fifty-five.

Terrell Owens

Terrell Owens was a highly successful NFL wide receiver, earning around $80 million during his football career. However, he filed for bankruptcy soon after retiring because of poor investment choices and large child support obligations. Owens had a lavish lifestyle and relied on financial advisors who didn’t handle his money well. He realized that without a regular income, he couldn’t afford his expenses. Since then, he’s appeared on reality TV shows to earn money in new ways.

Scottie Pippen

Scottie Pippen faced significant financial difficulties throughout his career due to unwise investments and poor legal counsel. He notably took legal action against a law firm after they lost $20 million of his money during a private jet purchase. He also experienced losses with several real estate investments that didn’t perform as expected. Despite these setbacks, Pippen continued to appear in the media to help improve his financial situation. Even with these past troubles, he remains a hugely recognizable and celebrated figure in the world of sports.

Vince Young

Vince Young, once a highly-paid first-round NFL draft pick, surprisingly filed for bankruptcy within a few years. Reports suggest he spent a large portion of his earnings on lavish parties and meals for teammates and friends. Adding to his financial troubles, he was sued by a payday lender over a loan he took out during a player lockout. His financial advisors were also accused of mishandling his money and taking out loans without his permission. Since then, he’s been working with his college to secure stable employment and get his finances back on track.

Lawrence Taylor

Lawrence Taylor is widely regarded as one of the best defensive players ever in the NFL, but he had significant financial difficulties after leaving the sport. He declared bankruptcy to save his New Jersey home. These money problems stemmed from years of struggling with substance abuse and legal issues. Poor investments and unsuccessful businesses also depleted the money he’d earned during his career. He’s been working hard for many years to address these personal challenges and rebuild his life.

Sheryl Swoopes

Sheryl Swoopes was a groundbreaking player in the WNBA, but surprisingly struggled financially after her successful career. Even though she was a superstar, she filed for bankruptcy because of bad financial decisions and the relatively low salaries paid in the league. At one point, she owed over $700,000 and didn’t have many possessions. Her story brought attention to the significant difference in pay between male and female professional athletes. Ultimately, she became a coach so she could continue working in basketball.

Boris Becker

Boris Becker was a hugely successful tennis player who made a lot of money through winnings and sponsorships. However, he recently went bankrupt after a London court found he hadn’t paid a long-term debt. Costly divorce settlements and poor management of his investments contributed to his financial difficulties. He also got in trouble with the law for trying to conceal assets when he declared bankruptcy. Since then, Becker has worked as a sports commentator to help pay off his debts.

Dorothy Hamill

Dorothy Hamill, a beloved Olympic gold medalist in figure skating, experienced financial difficulties and filed for bankruptcy in 1996. This was largely due to a failed investment in an ice skating show company, and was compounded by personal issues she faced while at the height of her career. Fortunately, she was able to overcome these challenges and continued performing in skating shows.

Riddick Bowe

Riddick Bowe, a former heavyweight boxing champion, surprisingly earned over $15 million in one fight. However, he soon faced financial hardship and declared bankruptcy after retiring. This was due to poor money management, legal problems, and difficulty adjusting to life after boxing. Expensive court battles stemming from personal issues further depleted his funds. Since then, he’s been making public appearances to earn a living.

Curt Schilling

Curt Schilling made over $100 million during his career as a Major League Baseball pitcher. However, he lost almost all of it after investing in a video game company that failed. Schilling personally funded the project and faced criticism when the company went bankrupt, eventually having to sell items like his iconic bloody sock to pay off his debts. Today, he earns a living through work in media and political commentary.

Warren Sapp

Warren Sapp was a highly successful NFL player who made over $80 million during his career. However, he surprisingly filed for bankruptcy in 2012, owing millions to creditors and the government. Despite owning a large sneaker collection, he had very little money in the bank. High child support costs and back taxes contributed to his financial difficulties. Since then, Sapp has worked as a sports analyst for several networks.

Eddy Curry

Despite earning over $70 million during his NBA career, Eddy Curry quickly found himself in financial trouble. He struggled with expensive loans and the significant costs of supporting a large family. Curry also faced lawsuits from people he owed money to, totaling millions of dollars. Ultimately, his poor financial management led to him losing his mansion and other valuable possessions. Since then, he’s been working on improving himself and building a more stable life after basketball.

Christian Laettner

Christian Laettner, a celebrated college basketball player who later played professionally in the NBA, experienced financial difficulties despite his early success. He faced lawsuits from former teammates and partners due to unsuccessful real estate ventures, and accumulated significant debt during the economic recession. These public legal disputes damaged his reputation. Ultimately, Laettner shifted his focus to coaching and running basketball camps for young players to revitalize his career.

Dennis Rodman

As a film and pop culture buff, I always found Dennis Rodman fascinating – a true original! But it’s pretty shocking to learn that despite being such a huge name during his NBA days, he really struggled financially after retiring. I read that he had serious trouble paying child support and covering legal costs from all the controversies he was involved in. Apparently, his lawyer once said he was completely broke and couldn’t even afford everyday things. I guess his wild personality and lifestyle made it tough to land consistent endorsement deals once basketball was over. Thankfully, he’s bounced back a bit by doing appearances overseas and being on reality TV, but it’s a stark reminder that fame and fortune don’t always last.

Diego Maradona

Diego Maradona, a legendary soccer player, continued to face financial difficulties long after retiring. While playing for Napoli in Italy, he reportedly owed the government a large sum in unpaid taxes – tens of millions of dollars. During visits to Italy, authorities frequently confiscated his personal belongings, like watches and jewelry, as a result. Even with his continued fame and work as a coach, he struggled to maintain financial stability. Despite these challenges, Maradona remains a beloved icon in the world of soccer.

Sugar Ray Robinson

As a boxing fan, it always saddened me to learn about Sugar Ray Robinson’s financial struggles. Despite being one of the greatest fighters ever, and earning a lot of money during his prime, he ended up with very little. He wasn’t irresponsible, exactly – he loved investing in things like a nightclub and helping people back home, but those ventures just didn’t pan out. He was incredibly generous, giving away a lot of his earnings to friends and neighbors. It got to the point where he had to keep boxing in exhibitions just to make a living. It’s a tragic irony that a legend like him didn’t leave behind the fortune you’d expect.

John Arne Riise

John Arne Riise, a former Premier League soccer star, surprisingly declared bankruptcy during his playing career. This was due to disagreements with his old agent and unsuccessful investments back in Norway. Despite earning a good salary, he found himself with debts he couldn’t cover. He eventually sorted out his finances, but the experience was a major lesson. Today, Riise works as a soccer coach and appears in the media.

Paul Gascoigne

As a sports fan, I remember Paul Gascoigne as an unbelievably gifted footballer – truly one of the best of his era. But watching his life after retirement has been heartbreaking. It’s a real tragedy to see how he squandered a fortune earned through his incredible talent. He battled serious mental health issues and addiction, and those struggles led to financial ruin, multiple bankruptcy attempts, and even the threat of losing his home. He’s spent years bouncing between rehab and trying to get his finances back on track. Gazza remains a hugely popular figure in England, but it’s a story with a deeply sad undercurrent.

George Best

George Best was a hugely talented soccer player known for his extravagant lifestyle, filled with expensive cars and parties. He battled alcoholism for many years, which ultimately led to financial difficulties after he retired from playing. Though he often made light of his spending, he actually struggled with money and sadly died with little wealth despite being considered one of the greatest players of all time. He’s remembered for both his amazing ability on the field and his troubled personal life, serving as a warning to others.

Share your thoughts on these shocking financial downfalls in the comments.

2026-01-06 21:17