Pete Rose

The IRS couldn't have cared less whether Pete Rose bet on baseball or not — it just wanted him to pay his damn bills. The disgraced ex-slugger failed to properly report income from autograph and memorabilia sales and gambling wins (horses this time). And even after Rose pleaded guilty to federal tax-evasion charges in 1990 and spent five months in prison, his troubles didn't stop there. In 2004 he was hit with a nearly $1 million lien for unpaid back taxes. Rose may have batted .303 in the majors, but when it comes to accounting, he strikes out every time.

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