At the time, Shields was on the last fight of his deal with the promotion and he was facing a true legend of the sport, who was making his return to action after one of the biggest knockouts in mixed martial arts history when Henderson flatlined Michael Bisping at UFC 100.
While Henderson had just inked a new multi-fight contract with Strikeforce, Shields was on the last bout of his current deal and he wasn’t going to re-sign right away. Instead, the veteran submission specialist decided to bet on himself as a massive underdog against Henderson.
“I didn’t re-sign with Strikeforce so I was going in as a free agent so I wanted to put extra pressure [on myself] cause I wanted to go to the UFC at that time,” Shields revealed when speaking to MMA Fighting on the 10th anniversary of their fight. “So it was a ton of pressure to win but it gave me the mindset to go in there and win no matter what.
“Henderson was coming off that knockout over [Michael] Bisping and he had the falling out with the UFC so it was a perfect opportunity. He was one of the biggest names in the sport and it was a perfect opportunity for me to go out there and get the win. I was a huge underdog but I always liked that. I went out there and it was a great fight.”
Shields had been competing at 185 pounds for less than a year, although he already had wins picked up two wins in the division including a submission victory over Robbie Lawler.
Some sports books had Shields listed as a 5-to-1 underdog to Henderson and the odds makers were nearly proven right during the opening round.
During an early exchange, Henderson connected flush with his signature right hand nicknamed the ‘H-bomb’ — the same punch that nearly decapitated fighters like Bisping and Wanderlei Silva. Shields dropped to the mat and it appeared his middleweight title reign was going to be rather short.
“The first round was really tough,” Shields said. “Going in there thinking don’t get hit with that overhand right and then I got hit with it right away. I don’t really remember getting hit. I remember looking up and there was Henderson and I was like ‘oh crap’ and that was right after he did that to Bisping. I didn’t want that to be me.
“I was on the ground, trying to get up, trying to catch singles, just trying to get my head cleared up. It’s kind of tough to keep fighting while you’re getting your head cleared.”
Things went from bad to worse when Henderson continued to bombard Shields with punches and before he knew it, he was back on the ground again.
“I ended up getting dropped a second time in that round. But I was really determined,” Shields said. “I just had to tough through and get my head back about me.
“I definitely can take a shot. That’s not what you want to get known for but I’m definitely capable of it.”
By the end of the opening round, Shields had started to get his feet back under him and he was able to recover even more during a one-minute rest period. As he met Henderson in the center of the cage for the second round, Shields knew this was probably a make or break moment for him to begin his comeback.
“I think by the end of the first round, I started to level out a little bit,” Shields explained. “I was still losing but I was doing better and I was starting to get my wits back. I wouldn’t say I was 100 percent [after the round] but I was able to come back in and take over and dominate the fight.”
From that moment on, Shields completely took over the fight.
Despite Henderson’s pedigree as a two time Olympic wrestler, Shields was consistently able to drag him back to the mat and control the action with his superior grappling skills. As Shields kept coming forward and looking for the takedown, Henderson struggled to defend himself and his gas tank started to drain.
“I would say maybe after the third round [Henderson was beaten],” Shields said. “Because the second round, I took him down easily but the momentum hadn’t completely shifted. The third round, when I took him down again that second time, I think I was kind of in his head. By the fourth and fifth round, it became domination.
“It was great to take him out, single leg after single leg against a wrestler. It wasn’t like I got lucky with one shot. I was able to take him down just about every round and when he got up, I was able to take him down again. It was nice to get the takedown repeatedly.”
In the end, Shields won a unanimous decision in what was certainly considered a massive upset at the time. The victory also gave Shields the bargaining power he needed to leverage himself into a deal with the UFC, which is the promotion he would call home six months later.
“When you’re a free agent in a fight, it’s a risky move because if you get knocked out, you’re not worth near as much,” Shields said. “It was super, super important to win that fight so it was great.”
After the fight was finished, Shields was being interviewed inside the cage but he was soon interrupted by Jason “Mayhem” Miller, who was in attendance that night. Miller was asking for a rematch after Shields had defeated him for the vacant Strikeforce title but this wasn’t a planned altercation set up by the promotion.
Miller’s confrontation led to a reaction from Shields’ teammates including Gilbert Melendez as well as Nick and Nate Diaz, who were inside the cage alongside him. A huge brawl broke out in the center of the cage with Melendez and the Diaz brothers going after Miller as security rushed into break up the melee.
The post-fight brawl got even more attention because the Strikeforce show was airing live on CBS, which also resulted in play-by-play commentator Gus Johnson remarking “sometimes these things happen in MMA.”
10 years ago today.— caposa (@Grabaka_Hitman) April 17, 2020
"Sometimes these things happen in MMA." pic.twitter.com/kfNUYQ5KK9
As much attention that’s been paid to the post-fight brawl over the last 10 years, Shields argues that it really didn’t take away from his victory that night. In fact, he compares that brawl to a similar situation that happened more recently when Khabib Nurmagomedov defeated Conor McGregor and then leapt over the cage to go after the Irishman’s teammates.
It was a bleak moment at the time but it didn’t erase Nurmagomedov’s dominant victory over the biggest draw in the history of the sport.
“Honestly, I don’t think it’s as bad as everyone makes it out to be,” Shields said. “Everyone still remembers the Dan Henderson fight. It’s kind of like the Khabib-Conor fight. Afterwards, the MMA media was like ‘oh he just tainted his career’ and all that but then you go talk to the actual fans and they loved it. So there’s a little bit of a disconnect between the MMA media and the actual fans.
“Everyone I talked to on the streets was like ‘that was the coolest thing I’ve ever seen, that dude Khabib was so bad!’ so I think the actual fans love these brawls but the media doesn’t, which is weird to me. It does overshadow it, but I don’t think it makes people forget the fight. Just like the Khabib-Conor thing. We talk about the brawl but everyone 100 percent remembers Khabib beating Conor. It just makes people talk about it more.”
When it comes to his feelings about Miller now, Shields says there’s no bad blood at this point, although the rivalry between his team and “Mayhem” definitely continued to simmer for a couple of years after that initial encounter.
“No, I don’t at all,” Shields answered when asked if he holds anything against Miller for that altercation. “I haven’t talked to Jason, but I have nothing against him. I know for a couple of years after we didn’t get along but at this point, I have no ill will towards him.
“I think he’s unfortunately not been doing the best mentally and I hope he is doing better and gets himself together. I know he’s been in jail a lot so I hope he gets himself together. I hope he’s OK.”
Ten years removed from that night, Shields still can’t believe that much time has passed but he always remembers his win over Henderson as one of the most important moments of his entire career.
“It’s definitely top three or four,” Shields said. “I’ve had a lot of big wins so it’s hard to pick one but there’s been a bunch of good ones. But that was definitely up there with my favorites.”
At 41, Shields is now back on the west coast while also splitting his time training in New York out of the Renzo Gracie academy in Manhattan. He hasn’t fought since 2018, although Shields makes it clear that he hasn’t retired yet.
For now, he’s just happy teaching and practicing Brazilian jiu-jitsu, booking the occasional grappling match and waiting for the next best opportunity to come along.
“Life’s been good,” Shields said. “I’ve been doing some jiu-jitsu. I haven’t officially retired from fighting but I haven’t fought in a while. If a fight really interested me and it got offered, maybe if it was somebody a little bit older, not one of these 20-year-old guys.
“But lately I’ve just been focusing on jiu-jitsu. Grappling matches are fun. The stress of fighting is gone. I don’t have to cut weight for jiu-jitsu but it’s a fun way to stay competitive.”