Unless you are a truly hardcore MMA fan, you probably don't remember Dan Henderson's early UFC career. It was during the dark ages of the UFC, and Henderson, with two fights and limited MMA training, went out and won a four-man tournament at 205 pounds. You would probably assume that he was facing off against guys that were just as limited as him, but he actually went out and beat two legitimate mixed martial artists. Allan Goes, who did not have any signature wins, had two of the most high quality draws in the sport against Frank Shamrock and Kazushi Sakuraba. And then in the finals, Dan fought Carlos Newton, who although was undersized for that weight class, became a UFC Champion by beating Pat Miletich a few years later. Those were guys with years of training and fights, and Dan Henderson walked in and beat them.
I should also mention that this began the legend of "Decision" Dan Henderson (the nickname was fair early in his career, even though he had enough huge finishes to make it obsolete by the end). Henderson had 22 of 47 of his fights go to decision, but that number is toned down due to late career Dan Henderson, with seven of his final eight fights being finishes. More incredible is he had nine split decisions in his career. Almost 20% of his fights were split decisions. I don't know where to find the records for that, so I'll just assume that Henderson is the Babe Ruth of split decisions.
After that, he went to Rings where he took out a couple of nobodies, and then on February 26, 2000, he had maybe the most impressive night in MMA history. In the first round, he faced Gilbert Yvel, who was 20-3 at the time and basically knocking out everyone that he faced (when he wasn't getting DQ'd), but Decision Dan would not be denied. Then he took on the greatest heavyweight fighter before Fedor Emelianenko, Antonio Rodrigo Nogueira. a man that only lost once in his first 21 fights. Unfortunately for Nogueira, that one loss was to Dan Henderson by split decision. After that, he took on Babalu in the finals. Babalu, a man who won his first twelve professional fights before taking on Henderson where he experienced the unlucky number 13, as Henderson won by majority decision. Yvel, Big Nog, and Babalu: There is nobody who has beaten anything close to that caliber of competition in a single night.
With that, Henderson made the move to Pride. Since this is Dan Henderson, he lucked into an easy fight to start off his Pride career, taking on the most terrifying fighter in MMA history, The Axe Murderer, Wanderlei Silva. Pride was the premiere organization at the time, and Silva didn't lose in his first 17 fights, and when he lost in his 18th, it was controversial. Although Henderson took his first loss, you could make a pretty strong argument that he won the fight.
He followed up his first loss by beating Renzo Gracie. That's a good win, but not too special. What was special was that Henderson won by knockout. He learned to throw a right hand, and that would become incredibly important later in his career.
I'd like to take a brief aside to address something. During this whole time, Henderson was still working on representing the United States in Greco-Roman Wrestling, as he didn't give up wrestling until 2001, when he had already twelve professional fights over four years without yet focusing on fighting full time. Yes, he had probably the greatest night in MMA history without even being a full time mixed martial artist. Dan Henderson was so fucking cool.
He finally bedcame a full time MMA fighter and fought in Pride for the next six years. Over that six year span, he lost four times, but only once was it to someone in his actual weight class. Otherwise, he lost to both Nogueiras and Ricardo Arona (which just reminds me how tough Arona was back in the day).
The highlights were mostly centered around that big right hand as Henderson started showing the ability to knock dudes out. He also became the first (and only) Pride Welterweight Champion (welterweight was 183 in Pride) by beating Murilo Bustamante, who is one of those legendary tough guys from Brazil that had his prime about 5-10 years too early.
But the biggest highlight was his rematch against Wanderlei Silva. It was the final fight in the history of Pride, and it was for the middleweight title. Henderson lost their first fight by decision, but he wouldn't let the same thing happen again as he about knocked Silva's head off in the third round to get the knockout victory and be the only guy in a major organization to hold titles in multiple weight classes at the same time.
And after all of that, he finally went back to the UFC.
Since it's Dan Henderson, there was no easing him in. he started with not one but two title matches in the weight classes where he held the belts in Pride. It, uh, did not go well. First, he lost a sluggish decision against Quinton "Rampage" Jackson. Then he took on Anderson Silva, where he took Silva down and dominated him in the first round. But by the second round, he decided game plans were for nerds and decided to just stand and trade with Silva where he got knocked silly and then choked out.
I guess now is as good of time as any to address something with Dan Henderson. He doesn't give a shit when he gets in a fight. His first goal is to knock someone's head off. Sure, he's an Olympic level wrestler where he could easily smother someone on top, but he almost exclusively used those skills to keep things standing so he could try to knock someone's head off. He could have been more successful had he stuck to a smart gameplan, but there is no way he could have been as awesome.
He got back on track after that with wins over basically the worst person in mixed martial arts, Rousimar Palhares, and one of the best people, Rich Franklin. After that, he coached on The Ultimate Fighter, opposite Michael Bisping, to set up their fight at UFC 100. It definitely wasn't his best win, but it probably was his most memorable, as Henderson destroyed Bisping with a right hand, and then gave him a leaping forearm for funsies. It was brutal and awesome all at once.
At this point, Henderson was probably only a fight away from a title shot, so he did what nobody else in the world would do, and left the UFC to go to Strikeforce, because Dan Henderson doesn't give a shit about titles when he can get more money somewhere else.
Henderson's Strikeforce career didn't start off the best. He gave Jake Shields one of the worst beatings I've seen in the first round of a fight and then totally ran out of gas and lost a decision. After that, he beat Babalu again and then took out Rafael Calvacante. Although he finished both guys, it's not going to make his career highlights. Then, since it's Dan Henderson, he took on the greatest heavyweight in the history of MMA, Fedor Emelianenko and proceeded to knock him out in the first round. This would be his last fight in Strikeforce, and he picked a hell of a way to go out.
In fact, let's look back on how Henderson left every organization he was in.
Brazil Open - Won Tournament
UFC - Won Tournament
Rings - Won Greatest Tournament Ever
Pride - Won Middleweight Title from scariest fighter ever, giving him two belts in different weight classes.
UFC - Most memorable knockout of his career, proved America's domination over England.
Strikeforce - Knocked out the greatest heavyweight of all time.
And even though he lost the final fight of his career, he did it in the perfect way, losing a close decision, because had he won, the UFC would have thrown a ton of money at him to fight again, and Dan Henderson does not turn down tons of money. There is no way he could have left these organizations on a higher note. This man knows how to increase his value at the right time.
When Dan Henderson went back to the UFC, he was already 41 years old, and age can catch up to anybody, even someone as great as Dan Henderson. Although he had two memorable wins over Mauricio "Shogun" Rua, he went 1-6 in his other fights with three losses coming by knockout.
But as important as timing his right hand, he also knew how to time his wins, and he was able to knockout Hector Lombard right as Michael Bisping was busy winning the UFC title. Somehow, despite going 4-6 in his last run in the UFC, he was given a title shot, because he's Dan Henderson, and that was the most interesting fight available.
His final fight gave you everything you could have asked for in a Dan Henderson fight. He landed a couple of those right handed bombs that nearly took out Bisping and gave Dan the early advantage. And then, like so many other times, he ran out of steam and Bisping started winning the later rounds. He put on a good final round, but there was only one way for "Decision" Dan's career to end. Sometimes those decisions went his way, this time it didn't. It was probably his best fight since the first Shogun fight, which happened five years prior, but at 46 years old, Henderson was able to show why he is one of the greatest fighters in history.
With a 32-15 record, it's tough to make the argument that he was the best fighter ever, but there is nobody who had a more interesting career than Dan Henderson. The guy fought in three weight classes (technically four, since the Brazil Open was close to the Welterweight limit), and fought nearly every interesting person in all of those divisions. Wanderlei, Fedor, A. Silva, Shogun, Cormier, Big Nog, Little Nog, Bustamante, Vitor, Franklin, Arona, Machida, and Rampage all fought Henderson at least once. He fought for two decades, and the only legends he missed over that period were Couture, Liddell, Jon Jones, Cro Cop, and Sakuraba. That's only five guys across three different weight classes over 20 years that Henderson couldn't find time to fight.
Dan Henderson had more big matches than anyone in the history of mixed martial arts. He is the world's most interesting fighter, and unlike the Dos Equis guy, there will never be a replacement for Hendo.