Bill Russell was an American basketball player and coach, best known for playing center for the Boston Celtics. He won 11 NBA championships. Russell is considered one of the greatest basketball players of all time.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 22 head-to-head matchups.
Most recently Bill Russell lost a matchup to Justine Henin (#2101) voted by someone from Germany.