Henry Kissinger was an influential American diplomat and political scientist. He served as the U.S. Secretary of State and National Security Advisor and was known for pioneering détente with the Soviet Union and opening relations with China.
This is based on winning 3 head-to-head matchups with other famous people, but also losing 15 head-to-head matchups.
Most recently Henry Kissinger lost a matchup to Dick Cheney (#316) voted by someone from Canada.