Chelsea Manning is an American activist and whistleblower known for disclosing classified documents to WikiLeaks. A former Army intelligence analyst, she was convicted in 2013 and had her sentence commuted in 2017 by President Obama.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 24 head-to-head matchups.
Most recently Chelsea Manning lost a matchup to Nelly (#417) voted by someone from Canada.