Winston Churchill was a British statesman and writer who served as Prime Minister during World War II and again in the early 1950s. He played a crucial role in leading Britain to victory and was awarded the Nobel Prize in Literature in 1953.
This is based on winning 54 head-to-head matchups with other famous people, but also losing 36 head-to-head matchups.
Most recently Winston Churchill lost a matchup to Evangeline Lilly (#535) voted by someone from United States.