Dan Henderson has twice fought for UFC gold. | Photo: D. Mandel/Sherdog.com
1. Dan Henderson
One can argue that by advancing through a one-night tournament at UFC 17 on May 15, 1998, Henderson won all that was available to win at the time. Still, although he bested Allan Goes and Carlos Newton to capture the middleweight bracket that night, it was not the same as having UFC gold wrapped around his waist.
Henderson left the UFC after three straight wins and joined rival promotion Strikeforce, where he captured the light heavyweight strap with a third-round knockout of Rafael Cavalcante in March 2011. After knocking out the legendary Fedor Emelianenko in his next outing, Henderson entered the UFC fray once again as a top contender, and a classic five-round triumph against Mauricio Rua in his return did little to alter that notion.
This is where the story takes a cruel turn. Henderson was all set to challenge Jon Jones for the light heavyweight strap at UFC 151, but a knee injury forced him out of the bout. When Jones refused to take a short-notice matchup against the opportunistic Chael Sonnen, the entire event was canceled; and it also turned out to be Henderson’s last best chance at glory. While Sonnen was eventually granted his wish to face Jones, Henderson lost three straight fights after the title shot that never was, pushing him down the 205-pound pecking order. Now 43 years old and with five fights left on a recently signed UFC deal, Henderson has a long hill to climb to get back into contention.