Harvey Milk was an American politician and the first openly gay man elected to public office in California, serving as a member of the San Francisco Board of Supervisors. He became an icon and martyr for the LGBT community.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 18 head-to-head matchups.
Most recently Harvey Milk lost a matchup to Mohammad Reza Pahlavi (#2124) voted by someone from Qatar.