Rajiv Gandhi was the 6th Prime Minister of India from 1984 to 1989. He was the youngest to hold the office, taking over after the assassination of his mother, Indira Gandhi. Awarded the Bharat Ratna posthumously, he was a significant figure in the Indian National Congress.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 23 head-to-head matchups.
Most recently Rajiv Gandhi lost a matchup to Kaley Cuoco (#904) voted by someone from Germany.