Garry Kasparov is a renowned Russian chess grandmaster, recognized for his record reign as World Chess Champion from 1985 to 2000. Known for his strategic prowess and success in numerous international tournaments, he later transitioned into writing and political activism.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 14 head-to-head matchups.
Most recently Garry Kasparov lost a matchup to Kate Moss (#405) voted by someone from Canada.