Silvio Berlusconi was an Italian media tycoon and politician who served as Prime Minister of Italy across multiple terms. He founded and led the center-right party Forza Italia and was a prominent media magnate owning Mediaset and AC Milan.
This is based on winning 23 head-to-head matchups with other famous people, but also losing 68 head-to-head matchups.
Most recently Silvio Berlusconi lost a matchup to Sylvester Stallone (#85) voted by someone from Canada.