Mike Tyson

Mike Tyson, once one of the highest-paid athletes, faced severe financial troubles despite earning millions. His lavish lifestyle, including extravagant spending on mansions, cars, and exotic pets, quickly drained his fortune.
Legal issues further compounded his financial woes, including a costly divorce and a prison sentence. By 2003, Tyson declared bankruptcy, with reported debts of $23 million. Poor financial management and trust in the wrong advisors also contributed to his downfall.
Allen Iverson

Allen Iverson, a former NBA star, faced significant financial troubles despite earning over $200 million during his career. Known for his extravagant lifestyle, he spent lavishly on jewelry, cars, and a large entourage. Poor financial management and lack of savings exacerbated his situation.
Legal issues, including a costly divorce and multiple lawsuits, further strained his finances. By 2012, Iverson was reported to be nearly broke. However, a trust fund established by Reebok, accessible in 2030, offers a potential financial lifeline.
Vince Young

Despite earning an estimated $35 million during his career as an NFL quarterback, Vince Young struggled to stay afloat financially. His lavish spending on luxury items, including cars, parties, and a massive entourage, quickly depleted his earnings. Poor financial management and ill-advised investments worsened his situation.
Legal issues, including lawsuits from creditors and disputes over unpaid loans, compounded his financial woes. By 2014, Young declared bankruptcy, listing assets between $500,000 and $1 million against debts ranging from $1 million to $10 million.
Antoine Walker

Despite a lucrative NBA career, Antoine Walker's financial journey took a dramatic downturn due to lavish spending and poor financial decisions. Known for his extravagant lifestyle, he spent heavily on luxury cars, jewelry, real estate, and gambling. Poor financial management, coupled with bad investments, rapidly depleted his fortune.
Legal issues, including lawsuits from creditors and financial institutions, exacerbated his situation. By 2010, Walker declared bankruptcy, citing debts of over $12.7 million.
Evander Holyfield

Evander Holyfield, a former heavyweight boxing champion, earned an estimated $230 million over his 26-year career. However, Holyfield faced severe financial troubles.
Between the lavish spending on his $20 million mansion to poor investments in a record label and restaurants, Holyfield was forced to declare bankruptcy in 2008. This led to the sale of his home, which only went for $7.5 million.
Charles Barkley

Charles Barkley, a former NBA star, faced money problems mainly due to his gambling habits. He admitted to losing around $10 million from gambling, which significantly impacted his finances.
Alongside his extensive spending on luxury items, these habits strained his wealth. The financial issues also affected his public image, leading to scrutiny and criticism. Despite his substantial earnings from his NBA career and later as a broadcaster, the financial mismanagement posed challenges.
Dorothy Hamill

Dorothy Hamill, the former Olympic figure skating champion, faced significant financial problems due to a combination of poor business ventures and lavish spending. She invested heavily in Ice Capades, a touring ice show, which ultimately failed, leading to substantial losses.
Additionally, her high living expenses further strained her finances. By 1996, the financial strain culminated in her filing for bankruptcy. This not only affected her personal wealth but also her public image and career opportunities.
Bernie Kosar

Bernie Kosar, a former NFL quarterback, faced financial turmoil despite a successful football career. His money issues stemmed from a series of bad investments, including ventures in real estate and businesses that failed to thrive.
Additionally, Kosar's high spending on family and friends, combined with costly divorces, further strained his finances. By 2009, he filed for bankruptcy, citing debts that overwhelmed his assets. This financial instability not only affected his personal wealth but also tarnished his post-football career, limiting his opportunities for endorsements and business ventures.
Johnny Unitas

Despite his legendary status in the NFL, Johnny Unitas still struggled with money. His issues arose from failed business ventures, including a series of unsuccessful restaurant investments and a failed circuit board manufacturing company. Additionally, Unitas had substantial medical expenses stemming from injuries sustained during his football career.
By the time of his death in 2002, he had accrued significant debt, which overshadowed his legacy and strained his family financially.
Bjorn Borg

Bjorn Borg, a tennis legend, encountered significant financial difficulties despite his on-court success. His money issues began with a series of failed business ventures, including a clothing line that did not meet market expectations and other investments that floundered.
By the early 1990s, he faced bankruptcy, which not only affected his personal wealth but also dimmed his post-tennis career prospects. The financial strain led to the liquidation of his assets and a tarnished legacy.
