Bernard Lawrence Madoff was an American financial criminal known for orchestrating the largest Ponzi scheme in history, worth an estimated $65 billion. Madoff also served as the chairman of the Nasdaq stock exchange.
This is based on winning 4 head-to-head matchups with other famous people, but also losing 18 head-to-head matchups.
Most recently Bernie Madoff lost a matchup to Keith Moon (#667) voted by someone from Canada.