Chris Weidman doubtful Dan Henderson retires if he wins middleweight title at UFC 204

The rematch between Dan Henderson and UFC middleweight champion Michael Bisping set for UFC 204 is one of those strange match-ups that pops up ever so often in this sport, a fight created less on merit and more to appease the will of the fans.

Henderson, at the age of 45, is one of the true legends of the game, and although nearly five years have passed since he last won back-to-back fights, his brutal finish over Hector Lombard at UFC 199 was convincing enough to allow him to step in as the No. 12 ranked middleweight and challenge for the title in his swan song before exiting into retirement.

Not surprisingly, the decision to allow Henderson to jump the line drew criticism from many within the UFC's middleweight division, most vocally top contender Ronaldo "Jacare" Souza. And while former UFC champion Chris Weidman shares Souza's disappointment, he also understands and can somewhat appreciate the uniqueness of the situation.

"I think it's kind of stupid, but I also don't like complaining about something that's already done," Weidman said Monday on The MMA Hour. "It is what it is, and because it's a done deal, you focus on the facts, and it's a cool thing for Dan Henderson. He's 46 years old and he gets the chance to retire with winning the belt. So you've got to be happy for him. I can't complain too much.

"I was complaining when it mattered, because I just didn't think he deserved the shot at all, and to set the precedent for the future of the sport, that is not good. It kind of takes away from working your way to fight for the title. I can go through his stats and his losses he's had recently, and I just don't think he deserves it. I don't think he could argue that he deserves it, but he's getting it, and so all the best to him."

In a roundabout way, Weidman is the one who started the middleweight division down the curious path it is now traversing when he pulled out of his rematch against Luke Rockhold due to injury just two weeks before UFC 199. With Weidman out, Bisping stepped in on short notice and stunned Rockhold, capturing the title with a memorable first-round knockout.

The unlikely victory gave Bisping a chance to finally call the shots, which then led to the rematch against Henderson at UFC 204, as Bisping has long wanted to avenge his infamous UFC 100 knockout loss to Henderson.

The two old rivals are now scheduled to face off Oct. 8 on Bisping's home turf in Manchester, England. Henderson reiterated his vow Monday on The MMA Hour that he is planning to retire after the bout, win or lose -- although Weidman wonders whether that plan will hold true if Henderson seizes the title.

"That would a gracious way to end his career," Weidman said. "He's one of my favorite fighters of all-time, even though I crushed his last couple of years and the fights that he's lost just because I don't think he deserves the shot at the belt, but he really has accomplished so much in this sport over the years, and for him to end up being a champion and retire that way would be amazing. But I still don't 100-percent believe it's going to happen that way.

"If he does win, which I think there's a good chance he does, I just think, you have to realize when you become champion, you have more opportunities. Your next fight will be for pay-per-view points and that's when you make the real money, so for him to retire on top and knowing that he could make millions of dollars in his next fight, it would be hard to see actually play out. I could see him, even if he thinks he's going to lose or whatever, whether his body hurts or not, I can't see him turning a million to a couple million dollar payday."

Ultimately Weidman has his eyes on facing the winner, even if he'll likely fight once before at UFC 205 in New York City before getting another shot at the belt. And while he won't flat-out pick Henderson to win, Weidman does see a scenario where "Hendo" is able to write a storybook ending to his 20-year MMA career.

"I think he has a great shot. I wouldn't say he's favored to win, but I'd say he has the same shot he had of knocking out Bisping as he did the first time. I don't think much has changed," Weidman said.

"It doesn't matter. Bisping will run from me as much as he possibly can, and Dan Henderson could retire. I really don't want to wish bad on anybody, like I hope this guy gets killed or beat. I really don't care either way. Either way, I've just got to keep winning and I'll have that strap back and have these big fights."