Sport: Football
Team: Dallas Cowboys
Hateful lowlight: Playoff record: 1-3

As the face of the Cowboys, Tony Romo is already in an unsympathetic position, but he's not doing himself any favors with that douchey backwards hat look and inability to win playoff games. Romo is the type of guy we should root for; he rose from relative obscurity and a D-II program to become one of the NFL's marquee players. However, his 6-year/$108M contract, affinity for John Mayer's ex-girlfriends, and propensity toward fourth quarter interceptions make him the most hated Cowboy since Butch Cassidy.