This Is the Way It Ends for Dan Henderson | FIGHTLAND

Artwork by Spencer Afonso

Dan Henderson had just put Wanderlei Silva into a deep sleep with a left hook to end Pride 33, and after he started speaking during the post-fight interview, the man holding the mic whispered for him to take out his mouthpiece. Pride was in a tailspin—that night in February 2007 ended up being the Japanese promotion's second-to-last event, and the evening's many upsets became a metaphor. Amidst that insanity, Henderson had done something big: by beating Silva, he became the only fighter to simultaneously hold two belts in a major MMA promotion, a distinction that still holds true today.

"I got no teeth," he told the interviewer. He smiled. Then he took the plastic out from his mouth and finished the interview with a big void across his upper gums, a memento his Team Quest teammate Randy Couture gave him during a sparring session. Along with a nose flattened by the wrestling mats that also crushed the cartilage in his ears, the cave entry in his mouth was a reminder of the price his body had paid to get him to where he was.

This Saturday at UFC 204, after a lifetime in combative sports and nearly 20 years in MMA and so much damage both absorbed and rendered, 46-year-old Dan Henderson—the oldest fighter in the UFC—offers his pugilistic swansong in a middleweight title fight against Michael Bisping at an ungodly local hour in Manchester, England. Win or lose, Henderson swears this is it. "I think I'm content with whatever happens," Henderson told ESPN. "Obviously, the only outcome in my head is that I'm going to win—but I'm ready for it to be over. I'm kind of looking forward to the different chapter I'm going to start after this fight."

The first pages of Henderson's MMA journey were written during the sport's cable-blackout prehistory, following a path that feels familiar even if it's his alone. After a decorated Greco-Roman wrestling career highlighted by Olympic appearances in 1992 and 1996, he won a single-night Brazilian no-holds-barred tournament in 1997 and the UFC 17 middleweight tournament in 1998. He took up with Couture and Olympic silver medalist Matt Lindland, and spent the next seven years jetting from his home in Temecula, California, to Japan. Over the span of 18 fights in Pride, he bounced around weight classes; despite his unimposing size, he twice fought former Pride and UFC heavyweight titleholder Antonio Rodgrio Nogueira.

In time, Henderson morphed from Olympic grappler to knockout artist with a right hand from hell, sort of like Chuck Liddell's better-groomed cousin. After taking the Pride welterweight title—the promotion's rough equivalent to the Unified Rules of MMA's 185-pound weight class—from Murilo Bustamante in 2005 and Silva's 205-pound title in 2007, he returned to the UFC when the promotion absorbed its rival. Henderson came up short in title unification bouts against "Rampage" Jackson and Anderson Silva, and the wins from his second run in the UFC were forgettable—except, of course, when he found Michael Bisping circling toward his right hand at UFC 100.

Contract negotiations spurred him to Strikeforce, and Henderson had a remarkable 2011: he knocked out Rafael Cavalcante to claim the light heavyweight title, TKO'd the great Fedor Emelianenko in the first round of their heavyweight bout, and returned to the UFC once again with a unanimous decision over Mauricio "Shogun" Rua in one of the most brutal things any of us will ever witness. It was as inspiring a run as any fighter over the age of 40 has ever had full of the kind of feats that makes a two-division champion grow into a Paul Bunyan figure, albeit the kind who'd sooner be pushing a grill down the street instead of chopping trees.

The uncomfortable truth, however, is that the back half of Henderson's career was fueled by synthetic testosterone. The testosterone replacement therapy era—when athletic commissions gave their blessings to fighters who used performance-enhancing hormones so as long as they had doctors' notes—looks less and less defensible the further it sinks into the past, and Henderson has the dubious distinction of being a pioneer of TRT in MMA, having started the treatment in 2007 for a low-testosterone diagnosis. When commissions suddenly outlawed exogenous testosterone, Henderson became the last fighter to compete with a TRT exemption, knocking out "Shogun" in a 2014 rematch. To his credit, Henderson never failed a test for performance-enhancing drugs prior to his testosterone replacement therapy (unlike Vitor Belfort, for example) and spoke openly and matter-of-factly about his use (also unlike Belfort), claiming that he tested himself to make sure he was always hovering around a normal range. (That's cold comfort for Bisping, who's arguably suffered more from the scourge of TRT than any other fighter.)

Whether it was the lack of helpful hormones, the age, or the mileage from the Rua fight and the others that preceded it, Henderson declined. He injured his knee and lost out on a light heavyweight title match with Jon Jones, which set in motion the events that would send UFC 151 up in smoke, and he's has gone 3-6 since that 2012 tipping point. He suffered the first knockout losses of his career to Belfort, and he looked helpless en route to getting choked out by now-champion Daniel Cormier in his last match at 205 pounds. The scariest part was that whenever a reporter broached the idea of retirement, Henderson acted like he never imagined the day coming.

But it's a funny thing how one win can wipe a memory clean, especially when it looks as cool as Henderson did when he elbowed Hector Lombard into unconsciousness at UFC 199 back in June. This time, Henderson told the crowd afterward "that could have been the last one of my career." Then his erstwhile nemesis Bisping won the middleweight title a few hours later, and goddamn if that didn’t sound like the makings of a better ending: the oldest fighter in the UFC gets the chance to recreate the past and exit stage left wearing the belt he could never quite reach before. Next thing you know, they're staring each other down, Bisping's talking his shit, and Henderson's mumbling his retort.

The Henderson-Bisping rematch has rightfully pissed off a lot of 185-pounders, Ronaldo "Jacare" Souza and Chris Weidman among them, who've earned their elevation in the rankings by winning with greater frequency. And yeah, this fight is a cash grab that wasn't booked for merit: it's part revenge opportunity for Bisping, who makes his first title defense in a totally winnable rematch over the guy who embarrassed him seven years ago, and part lifetime achievement award for Henderson. But there's every reason to believe that Henderson is serious about retiring in a way that almost every other MMA fighter is not because he hasn’t flirted with the idea until now, and at 46 years old, he can't physically keep putting his body through a meat grinder anymore. He's always been a walking callous of a man, but look at this week's staredown with Bisping, and he looks like he's beginning to turn to stone. We've all seen the price his body has paid, and it seems like he's finally noticed it, too.

Looking back at Dan Henderson's fighting legacy, it's strange that the coda arrives like this: fighting at about 5 a.m. local time in England, against an old foe for an accolade that's always eluded him. But if he keeps his word, this is really the way it ends. If it ends the way he wants, he'll be smiling once again, and he'll have time to put in his dentures. 

Check out these related stories:

The Tactical Guide to Bisping vs. Henderson II

The UFC Is Bracing for the Fallout of UFC 204 With an Unofficial Middleweight Tournament

Bisping Opens as Sizeable Favorite Over Henderson