Sport: Baseball
Team(s): St. Louis Cardinals
Champion: 1967 World Series
Offense(s): Drug possession
Sentence: Five years. Served 10 months.

Following a bright career which included 11 All-Star game appearances, a 1967 MVP award, and a World Series in that same year, Orlando Cepeda went down a dark path after his retirement from the game. In 1975, Cepeda led a baseball clinic in Colombia and in that time, met a couple drug dealers who convinced the former MLB player to smuggle drugs into two boxes containing clothing back to Puerto Rico. After returning to PR, Cepeda waited nearly two weeks before requesting the boxes. After a brief snag in retrieving the items, the boxes were sent to Cepeda's car where he was arrested for drug possession.

While going through trial for drug possession, another individual came forth claiming that Cepeda pointed a gun at him and if that weren't enough, an ex-wife sought more money in child support and alimony. Cepeda was eventually sentenced to five years, but was freed after 10 months.