Year: 1999
Yeah, many athletes have done the whole cross-dressing bit but how many have appeared on the cover of a national magazine in drag? In 1999 after Mike Ditka and the Saints traded the house to draft Ricky, ESPN The Magazine shot this memorable wedding cover of the rookie and his coach. This marriage between the eccentric running back and menacing coach last just one season as Ditka was fired after the '99 season.