Dan Henderson: 5 Defining Moments

Generations from now, combat sports aficionados will talk about a handful of MMA legends. Dan Henderson will be one of them.

Still the only fighter to simultaneously hold major mixed martial arts championships in two divisions, Henderson has carved out a legacy that will stand the test of time. The 45-year-old Downey, California, native will look to add to his lengthy list of historic exploits at UFC 204 on Saturday, when he challenges Michael Bisping for the Ultimate Fighting Championship middleweight crown. There, Henderson will attempt to become the first mixed martial artist in history to win titles in Pride Fighting Championships, Strikeforce and the UFC. Even if he were to fail in his bid, “Hendo” can rest easy at night. Victories over a litany of contemporaries, MMA stars and fellow all-time greats -- Bisping, Mauricio Rua (twice), Fedor Emelianenko, Rich Franklin, Wanderlei Silva, Vitor Belfort, Murilo Bustamante (twice), Renato Sobral and Antonio Rodrigo Nogueira -- leave him a with a resume few can match.

In a career with plenty of defining moments, here are five that stand out:

1. Double Take

No one inspired fear and wonder within Pride Fighting Championships quite like Silva. Though he grew more susceptible to knockouts as the years passed and the miles accumulated on his body, there was a time when “The Axe Murderer” was virtually unbeatable; and despite a head kick knockout loss to Mirko Filipovic in the 2006 Pride open weight grand prix semifinals a few months prior, Silva was still a dominant force when he put his 205-pound title on the line against Henderson at Pride 33 on Feb. 24, 2007. However, “Hendo” flattened the Brazilian in the third round, leaving some to wonder whether or not Silva’s career might be over. Silva faded late in the fight -- it was later revealed that he entered the ring battling an illness -- and tried unsuccessfully to connect with one of the clubbing right hands for which he had become known. Henderson countered with a crushing left hook, as Silva fell to his back, his arms extended at his side. He did not have the wherewithal to stop the devastating right hammerfist that came next and finished the job. Henderson broke into an immediate celebration, the knockout making him the first fighter in history to hold major MMA titles in two weight classes at the same time.

2. Nuclear Strike

The weapon that made Henderson famous was his ridiculously powerful right hand, and no one knows the sting of that punch any better than Bisping. Neither man cared for the other as they entered their matchup at UFC 100 on July 11, 2009. They had served as opposing coaches on Season 9 of “The Ultimate Fighter,” and Henderson vowed then to knock out the bombastic Englishman. It took longer than perhaps he anticipated, but Henderson’s right hand made its way to Bisping’s face in the second round. “The Count” backed away from the advancing Henderson but made the inexcusable mistake of circling towards the Californian’s power hand. Henderson stepped in an unloaded with a rolling overhand right and sent an unconscious Bisping crashing to the canvas stiff as a board. The H-Bomb had detonated, but Henderson was not finished. He left his feet and dropped a diving right hand on the defenseless Brit, an unsettling and lasting reminder of the bad blood that had developed between the two.

3. War of Attrition

In an epic encounter between two former Pride Fighting Championships cornerstones, Henderson emerged victorious. Backed by his vicious right hand and indomitable will, Henderson captured a narrow unanimous decision from Rua in the UFC 139 headliner on Nov. 19, 2011 at the HP Pavilion in San Jose, California. The Team Quest co-founder was the dominant force in rounds one through three, as he wobbled Rua numerous times with his thudding right hand. They exchanged violently throughout the grueling 25-minute battle. Rua seemed to teeter on the brink of defeat more than once, including in the third round, where Henderson blasted the Brazilian with right hands, followed him to the canvas and swarmed with hammerfists. Somehow, “Shogun” survived, but when he rose to his feet, he was a battered and bloodied mess, his white shorts stained pink. The tide turned in Rua’s favor in the fourth round, as he stunned Henderson, struck for multiple takedowns and mounted the former Olympian. With Henderson clearly on fumes, Rua capitalized across the final five minutes, as he scored with an early takedown and kept Henderson pinned to the mat. He mounted the former two-division Pride champion five times in the fifth round, only to fall short on the scorecards in one of the most unforgettable fights in MMA history. “That guy can take an [expletive] punch. I hit him hard,” Henderson said. “I thought I could finish him in the first two or three rounds. He finished the fight strong, but I thought I had the first three rounds easily. I should have had him finished, but the gas tank was running a little low at that point. It very well could be [the toughest fight of my career]. It started out strong for me, but he hung in there with great heart, like a champion should.”

4. Tournament Tested, UFC Approved

Henderson has been the last man standing in a number of tournaments throughout his career, from the 1997 Brazil Open lightweight tournament and the 1999 Rings King of Kings tournament to the 2005 Pride Fighting Championships welterweight grand prix. It seems somehow fitting then that Henderson introduced himself to Ultimate Fighting Championship fans in just such a setting. He was 27 years old when he threw his name in the middleweight tournament at UFC 17 on May 15, 1998 in Mobile, Alabama. Henderson was joined in the four-man draw by Brazilian jiu-jitsu black belt Allan Goes, Bob Gilstrap and future UFC welterweight champion Carlos Newton. He moved ahead in the tournament with a 15-minute unanimous decision over Goes in the semifinals; Newton advanced by submitting Gilstrap with a triangle choke in 54 seconds. They locked horns in the final, where Henderson outlasted Newton and walked away with a split verdict over the Canadian grappler. No one could have known that he was on his way to fashioning a hall-of-fame resume that would span two decades.

5. An Unexpected Wrinkle

Henderson authored one of the most memorable knockouts of his unrivaled career at UFC 199 on June 14, 2016, as he cut down Hector Lombard with a head kick and a slashing backward elbow in the second round of their featured middleweight clash. Henderson flipped the switch on the Cuban judoka 1:27 into round two. Both men were confronted by adversity in the first round. Henderson staggered the onetime Bellator MMA champion with his fabled right hand, only to have the American Top Team rep fire back with a short left and follow with a takedown. Later in the round, Lombard leveled “Hendo” with a clean left hook; a finish seemed near and inevitable. Henderson withstood the blows, however, and pushed the fight into the middle stanza. There, he connected with the head kick, followed with the elbow and landed two more blows on the already unconscious Lombard before referee Herb Dean could arrive on the scene. It was the 16th knockout victory of Henderson’s 46-fight career but the first associated with a kick.