The former two-time Olympian first entered the sport in 1997 where a 2-0 record eventually brought him to the UFC the following year. In a single night, Henderson put himself on the map when he bested Allan Goes and future champion Carlos Newton—clinching the UFC 17 tournament title in the process.
Next, Henderson entered a 32-man tournament—one of the largest in mixed martial arts history. Fighters like Gilbert Yvel, Renato Sobral, Alistair Overeem and Antonio Rodrigo Nogueira were part of the talent-laden field of combatants, though the rugged and raw Henderson reigned supreme overall.
The Team Quest product continued to cultivate his legend overseas when he entered Pride in 200, suffering his first career defeat at the hands of light heavyweight great Wanderlei Silva.
The loss didn't hold back the Temecula fighter for long—Henderson clinched victories over Renzo Gracie, Yuki Kondo and former UFC champ Murilo Bustamante along the way, inviting the Californian to take part in the organization's first and only 183-pound Grand Prix.
Henderson deftly defeated a field of eight and later used his success to earn a rematch with rival Wanderlei Silva, who Henderson exploited with his devastating left hook. He earned the emphatic knockout over the Brazilian heavy hitter.
As time passed, Henderson advanced in age, though his skills were unwavering.
After years spent competing among the elite of the middleweight class, the cut to the 185-pound division became more and more tedious.
It became largely evident in April of 2010 when a sluggish and fatigued "Hendo" dropped a lackluster decision to then-Strikeforce champion Jake Shields.
Afterward, the touted veteran abandoned the middleweight class and has since looked stellar. Henderson is currently riding a four-fight win streak that includes knockout victories over Renato Sobral, Rafael Feijao and Fedor Emelianenko—which was contested in a heavyweight tilt.
After claiming the Strikeforce 205-pound title, Henderson re-entered the Octagon last November where he took on fellow Pride legend Mauricio "Shogun" Rua. In a back-and-forth, rollicking battle, Henderson emerged victorious in what has been regarded as the greatest fight of all time.
Henderson has since hit his stride in the light heavyweight class and looks to be 10 times the fighter he was in his disappointing affair against Shields.
His knockout power is still evident—even in a higher weight class—and disparity in size doesn't seem to be an issue: Henderson's natural strength rivals most.
The light heavyweight class is a good fit for the would-be UFC Hall of Famer, who continues to make waves in the MMA world even at 41 years old.