Watch Jeb Bush’s Saddest Campaign Moments

Jeb Bush’s campaign has fallen short of expectations.

At one time the Republican front-runner with substantial money behind his campaign’s super PAC, the former Florida Governor was the man to beat. Then, billionaire Donald Trump emerged as a more serious contender than his veteran team had anticipated.

Bush never quit figured out how to deal with him, and finished well behind him Saturday in South Carolina. It was the latest example of Bush winding up with disappointing results despite earnest efforts.

TIME’s Philip Elliot narrates a string of clips that highlight Bush’s fall. There is evidence of his awkwardness on the campaign trail, which may have cost him dearly after a promising start. No amount of his presidential lineage can overcome a political moment that rewards outsiders and punishes experience.