Slobodan Milošević was a Yugoslav and Serbian politician who served as President of Serbia and later the Federal Republic of Yugoslavia. Known for his role in the Yugoslav Wars, he was the first sitting head of state to be charged with war crimes.
This is based on winning 3 head-to-head matchups with other famous people, but also losing 15 head-to-head matchups.
Most recently Slobodan Milošević lost a matchup to Maggie Smith (#410) voted by someone from Germany.