Lee Kuan Yew was the first Prime Minister of Singapore, serving from 1959 to 1990. He is widely regarded as the founding father of modern Singapore, transforming it into a highly developed country.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 31 head-to-head matchups.
Most recently Lee Kuan Yew lost a matchup to Gary Coleman (#1219) voted by someone from United States.