Sport: Baseball
Team(s): Detroit Tigers
Champion: 1968 World Series
Offense(s): Drug trafficking, embezzlement, and racketeering; conspiracy, theft, money laundering and mail fraud
Sentence: 23 years but served two after reaching plea bargain; 12 years, however, only served 6 years.

Denny McLain had a memorable 1968 campaign. After going 31–6 with a 1.96 ERA, McLain led the Tigers to a World Series title and became the first American League pitcher to win the MVP and the Cy Young Award in the same season. After his career took a turn for the worse, thanks to an astronomical weight increase, McLain started a betting ring backed by the Mafia.

After getting hit with drug trafficking, embezzlement, and racketeering charges, the pitcher was sentenced to 23 years in prison in 1985. After only two years, McLain was a free man again after what is being referred to as procedural violations. Then, the government re-indicted McLain and found him guilty. He was supposed to serve a 12-year sentence, but once again, he was let out early.