Donald Rumsfeld was an American politician and diplomat who served as Secretary of Defense under Presidents Gerald Ford and George W. Bush. He played a central role in the U.S. invasions of Afghanistan and Iraq.
This is based on winning 3 head-to-head matchups with other famous people, but also losing 17 head-to-head matchups.
Most recently Donald Rumsfeld lost a matchup to Monica Bellucci (#648) voted by someone from Canada.