Thaksin Shinawatra, a prominent Thai businessman and politician, served as the 23rd Prime Minister of Thailand from 2001 to 2006. He founded Advanced Info Service and the telecommunications conglomerate Shin Corporation, becoming one of Thailand's richest people.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 25 head-to-head matchups.
Most recently Thaksin Shinawatra lost a matchup to Eddie Redmayne (#564) voted by someone from United States.