Kellyanne Conway is an American political consultant and pollster who served as Senior Counselor to President Donald Trump from 2017 to 2020. She was the first woman to manage a successful U.S. presidential campaign.
This is based on winning 6 head-to-head matchups with other famous people, but also losing 9 head-to-head matchups.
Most recently Kellyanne Conway lost a matchup to Brittany Murphy (#876) voted by someone from Canada.