Raúl Castro served as the First Secretary of the Communist Party of Cuba from 2011 to 2021 and as President of Cuba from 2008 to 2018. He played a significant role in the Cuban Revolution and held various key military and political positions.
This is based on winning 3 head-to-head matchups with other famous people, but also losing 16 head-to-head matchups.
Most recently Raúl Castro lost a matchup to Viggo Mortensen (#1002) voted by someone from Canada.