Denny McLain
Baseball Player
3-time All-Star and 1968 World Series Champion pitcher for the Detroit Tigers who became involved in organized crime, leading to bankruptcy, multiple arrests, and jailtime.
He played shortstop and pitcher at Mt. Carmel High School in Chicago, Illinois.
After serving out a half-season suspension when his gambling came to light, he never regained his dominance, and retired to focus on gambling full-time.
He married Sharyn Boudreau, the daughter of former MLB star Lou Boudreau.
With his tragic and entirely predictable downfall, he joined the ranks of Pete Rose and the Chicago Black Sox as cautionary tales of wealth and arrogance in professional baseball.