26. Mike Tyson
Mike Tyson, the erstwhile heavyweight champ known for his $30 million fight earnings, found himself over $27 million in debt, per a 2003 report. Owing IRS, facing divorce, and child support payments led to his bankruptcy filing, highlighting a struggle starting from 1998.

Attempting a financial comeback, Tyson ventured into acting, initiated a podcast, and explored investments. His journey towards reclaiming his fortune illustrates resilience beyond the boxing ring, showcasing a different side of the legendary fighter.
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