Jacqueline Kennedy Onassis was the First Lady of the United States from 1961-1963. Known for her dedication to preserving historic landmarks and her unique fashion sense, she became an international icon. She later had a successful career as a book editor.
This is based on winning 6 head-to-head matchups with other famous people, but also losing 11 head-to-head matchups.
Most recently Jacqueline Kennedy Onassis lost a matchup to Robert F. Kennedy (#22) voted by someone from Finland.