Ben Askren
Olympic Result: 7th place, 2008
It’s crazy to think that, at one time, Ben Askren wouldn’t have featured on this list, because UFC President (and now CEO) Dana White simply didn’t seem to want him in the promotion.
That all changed with the infamous “trade” between ONE Championship and the UFC, which saw flyweight great Demetrious Johnson swapped for Askren. In hindsight, ONE got the better of the deal, getting more mileage out of Johnson, while Askren, already encountering hip problems, would win a single fight (over Robbie Lawler) before losing to Jorge Masvidal and Demian Maia, then calling it a career.
At the other end of his martial arts journey, Askren was a two-time NCAA Division I champ who would earn himself a spot on the U.S. Olympic team. He won the U.S. National Championship in 2007 to do so, and repped the U.S. at the 2008 Summer Olympics, winning his opening round match. He then lost to Ivan Fundora, finishing 7th overall.
A one point in his wrestling career, Askren boasted an 87-match winning streak. He started his MMA career 19-0 outside of a single no contest that left Luis Santos unable to continue. He’d retire with a 19-2, 1NC record.