Pete Rose

Pete Rose has encountered the IRS on multiple occasions for failure to pay all his taxes.

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Good ol' Charlie Hustle! Or should we pity Charlie Hustle, the everyman singles hitter who holds the record for career hits but was banned from Major League Baseball and denied a sure shot at the Hall of Fame? It turns out that not only did Rose bet on sports (denying he bet on baseball while managing the Reds, despite bookie sheets, phone records, and accusatory statements from friends and associates), but he also failed to report the winnings to the IRS. In 1990, that coupled with failure to report earnings for personal appearances, autographs and the like, landed him five months in jail, a $50,000 fine and 1,000 hours of community service [source: LA Times].

Then, in 2003, it looked like a doubleheader, with Rose back in the IRS dugout due to another failure to pay. But this time the charge remained civil instead of going criminal, and Rose managed to pay the $154,000 lien against him without, for example, selling his million-dollar Los Angeles condo.

The moral of the story: Don't play hardball with the taxman.