Michael Bloomberg is an American businessman and politician who co-founded and served as CEO of Bloomberg L.P. He was the mayor of New York City for three terms and a candidate for the 2020 Democratic presidential nomination.
This is based on winning 13 head-to-head matchups with other famous people, but also losing 18 head-to-head matchups.
Most recently Michael Bloomberg lost a matchup to Anderson Cooper (#1132) voted by someone from Canada.