Jesse Jackson is an American civil rights activist and politician who emerged as a key figure during the civil rights movement. He founded the Rainbow/PUSH organization and ran for the U.S. presidency in the 1980s.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 14 head-to-head matchups.
Most recently Jesse Jackson lost a matchup to Ang Lee (#2149) voted by someone from Canada.