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 7 head-to-head matchups with other famous people, but also losing 19 head-to-head matchups.
Most recently Harvey Milk lost a matchup to Lisa Marie Presley (#644) voted by someone from Canada.