No. 8: Denny McLain

The last Major League pitcher to win 30 or more games in a season, Dennis "Denny" McLain went 31-6 in 1968 for the World Series-winning Detroit Tigers, earning him the American League Cy Young and Most Valuable Player awards – the first pitcher to do so in the same season.

But associations with gamblers and criminals eventually shortened McLain's career. After being suspended for much of the 1970 season, McLain never regained his form, and in 1972, played his last game in the majors at age 28.

During the 1980s, McLain would spend more than two years behind bars on charges of embezzlement, racketeering and cocaine possession.

After getting out of prison, McLain reportedly played the organ at a Michigan bar where former boxer Leon Spinks worked as a bartender.

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