Glen Beck - he's not the biggest loser, but he will lose his media empire, because he jumped the shark (Fonzie reference) with the cheeto dust on his face skit; and that's saying something for a guy who promised ground breaking revelations he never delivered. I don't hate him - I liked the detailed chalk diagrams showing the in and out rotation of non-profits to federal positions to businesses showing how all these various high players were related and interacting.
Romney - he lost in 2012, and he didn't seem big on being politically resurrected, so he really didn't lose anything
Paul Ryan - still speaker of the house, still influential unless loses his position in 2017 - you just get alienation between him and President Trump in 2017 if Ryan continues to follow party leaders versus the party base.
The Bushes - they lost and lost BIG this election, from Jeb being the presumptive nominee to essentially everyone they endorsed losing; Cruz lost points when he hired a Bush relative and several of Bush's staffers on his team.