#7: Warren Sapp
The tale of this former defensive powerhouse, who once donned the jerseys of the Tampa Bay Buccaneers and Oakland Raiders, took an unexpected twist in 2012 when he found himself navigating the choppy waters of bankruptcy. As per Tampa Bay Times reports, what prompted this financial reckoning was a loan gone sour, tied to a failed endeavor aimed at constructing affordable housing in St. Lucie County. The weight of his debts at the time reached a staggering $6.7 million.
It’s a financial paradox that becomes all the more perplexing when you consider that during the pinnacle of his career, he inked three NFL contracts worth a cumulative $76 million. On top of that, he enjoyed a substantial annuity and pension amounting to approximately $1 million, boasted assets valued at $6.4 million, and pocketed earnings from lucrative endorsement deals, reality show appearances, speaking engagements, and even a book deal.