Lawrence Taylor (Bankrupt in 2009): Many high-priced NFL stars would be happy to spend a few bucks for an edge on their competition. But buying hookers for the opposing teams in an effort to “tire them out?” That’s something only LT would do. During his heyday, the Giants linebacker recorded a league-leading 20.5 sacks and became one of just two defensive players to win the NFL Most Valuable Player award. But by his own admission, he was spending thousands daily on drugs and partying. Business decisions also hurt his finances, notably the 1993 venture in All-Pro Products which went public but then folded in less than a year. Then in 1997, Taylor pleaded guilty to file false income taxes at the end of his football career. Off the gridiron, the troubles only got worse as spotty analyst work dried up and legal troubles including statutory rape charges took their toll.
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