Jeopardy! champion last Friday but lost the title on Monday night. Freeman wore a trans flag pin to quietly represent the community on the show.A financial analyst, Freeman took home $5,559 in cash winnings.Related: RuPaul was on Jeopardy last night & she won it all“I spent a lot of time learning about and reflecting on my gender identity in grad school, coming out as transgender and lesbian a few months before graduating,” Freeman told MLive.