'Perfect opponent': Oliveira, Chandler's winding careers converge again at UFC 309

NEW YORK — As a pair of action fight veterans who have recently watched long-awaited opportunities evaporate due to forces beyond their control, it’s fitting that Michael Chandler and Charles Oliveira’s winding career paths will converge Saturday night.

In mid-2023, Chandler was preparing for a lucrative fight with UFC’s biggest draw, Conor McGregor, while Oliveira was entering camp for a rematch with its lightweight champion and pound-for-pound king, Islam Makhachev. But both fights fell through. Neither was rebooked. And by mid-2024, Chandler and Oliveira were left adrift amid the sea of lightweight contenders.

So, they agreed to commiserate together over as many as five rounds in a co-main event at UFC 309. Such prominent placement on a Jon Jones pay per view at Madison Square Garden is reason enough to sign up for this fight. But it still feels like, despite the truculence of both competitors, this isn’t as much the fight that they want, as the fight they can get.

“I’ve had my moments — moments of doubt, moments of wanting things to move forward, wanting to get to the next thing, wanting fights to be booked,” said Chandler, who will be competing for the first time in two years Saturday night. “But patience is a virtue, right? It is one of the most important attributes that we can have as human beings.”

Those are the words of a guy who spent the last 24 months awaiting a McGregor fight — not to mention the substantial windfall attached to it — that never materialized. Meanwhile, Oliveira went the opposite route after his big fight fell through, putting his No. 1 contendership on the line at UFC 300 against Arman Tsarukyan while Makhachev was sidelined with an injury.

Different approach, same outcome. Oliveira dropped a razor-thin split decision to Tsarukyan and left the Makhachev fight behind in the octagon. Sitting out, gambling a title shot — these are the risks you take in this business. But harsh consequences occur when those risks are realized.

Tsarukyan is now booked to fight Makhachev for the title in January. And with recent wins over UFC’s No. 3 and 4 lightweights — Justin Gaethje and Dustin Poirier — Oliveira’s out of contenders to challenge. Chandler, meanwhile, just needs a fight, lest he burn any more late-career runway. And so, here we are.

“I know [the Tsarukyan fight] was highly debatable. Some people think he won. I think I won the first and the third round,” Oliveira said. “But that’s in the past right now. The one thing I took away from it is I'm not going to wait. I'm not going to wait for the fight to come to me. I'm going to push forward, hunt, and get to that fight.”

Oliveira is a fighter’s fighter who halted an inconsistent early-career arc — the submission artist went 10-8 with a no-contest over his first seven years in UFC — when he switched camps in 2018, joining Rudimar Fedrigo’s Chute Boxe Academy in Sao Paulo, Brazil. He promptly ran off a 9-fight win streak, culminating in his knockout of Chandler to claim the vacant lightweight title in 2021.

Following a hair-raising first round in which both fighters survived near night-ending moments, Oliveira snatched the belt via TKO only 19 seconds into the second after rocking Chandler twice with lefts:

Oliveira somehow topping the theatrics of that moment on Saturday seems next to impossible. And it’s hard to say what another win over a lower-ranked fighter he’s already beaten would do for his lightweight contendership. He could sit out and convincingly argue he deserves to be next to fight for the title already. 

He was controversially stripped after missing weight by half a pound during an event at which numerous fighters — Chandler included — took issue with the accuracy of the scales. His loss that night to Makhachev was his first in nearly five years. He was already booked for a rematch but had to pull out late after suffering a cut while training. But Oliveira doesn’t care to play those games.

“Everybody comes here and says the same thing. They talk the talk. They say they have plans. I think we have to come here and do things,” Oliveira said. “My legacy, I think it was built with everything that I've done. The records, the bonuses, the finishes, the knockouts. It's the way I approach things, the way I fight, the way I behave.”

Chandler, at least, could improve his standing in the division with a victory over the former champion. But, at 38 and coming off losses in three of his last four, is he really positioned for a title reign? Or is his best outcome still a fight with McGregor at welterweight that could materialize late in 2025?

“The way that I see it is that this is the way that it was always supposed to be. That this opportunity, getting my hand raised on Saturday night, gets me to the number one contender spot and I fight for the title next," Chandler said. "And it just so happens that it's against the guy who shattered my dreams of becoming the lightweight champion.”

Now, you could accuse Chandler — currently UFC's No. 7 ranked lightweight — of getting a little ahead of himself here. No record or result guarantees anyone a title shot in this sport. Just ask Tom Aspinall. But Chandler’s core identity is to be that self-assured, shouting things into existence like he’s David Goggins on his 100th mile. Ahead of himself? How about taking things even further.

“And we’ve got other options. Max [Holloway] for the BMF belt, Islam for the title, the Connor fight,” Chandler said. “Colby [Covington] comes to mind at 170. I think that would be a fun one. I’m in a ridiculously awesome spot right now when I beat Charles Oliveira.”

Again, Chandler’s 38 and coming off losses in three of his last four. Now he’s talking about beating Oliveira Saturday, becoming the No. 1 lightweight contender, taking a side quest for a super fight with McGregor at 170, returning to 155 to win the belt from Makhachev or Tsarukyan, flirting with 170 again, defending at 155, running for congress, landing on the moon. It’s an awfully ambitious roadmap.

And yet, this is what Chandler’s done since entering UFC at 35 and declaring that he was “not here for a long time, here for a good time.” His first two years with the company were a speed-run of action fights against the who’s who of lightweight contenders. 

Knocking out Dan Hooker in his UFC debut; getting knocked out by Oliveira in a back-and-forth title bout; narrowly losing a barnburner to Gaethje that was widely considered the 2021 fight of the year; flattening Tony Ferguson with a front kick knockout; and getting submitted late in a wild, chaotic clash with Poirier.

But two years spent waiting for McGregor has faded the colours of those moments. And Chandler’s explosive, all-out style isn’t going to be an easy one to sustain into his 40’s. If he continued waiting for a McGregor fight that never materialized, he would have wasted the final high-earning years of his career. Much of the damage may already have been done.

“I have no regrets. I’m not mad at the sport. That's the way the sport goes,” Chandler said. “Ultimately, Charles is just another guy with two arms and two legs who's my size. I get to perform in front of the Madison Square Garden crowd, get to blow the roof off the place, steal the show. And reintroduce myself to the mixed martial arts world and the sporting world — show them who I am, why I fight, and who I fight for.”

Now, there is an awkward tension to this fight. Win or lose, Oliveira remains a top lightweight with losses to the current champion and No. 1 contender. Win or lose, Chandler remains a top lightweight with losses to multiple contenders currently ranked above him. The best possible result for both fighters appears to be a memorable, back-and-forth contest in which neither athlete sustains enough damage to preclude them from fighting again in the first half of 2025. 

That creates a paradox in which both fighters need to push the action but lack high-stakes incentive to truly lay it all on the line. Why would you want to leave a piece of yourself in the octagon during a five-round war in pursuit of an outcome that leaves you on the shelf for the better part of a year and only spins your wheels in the division?

But that’s how rational fighters think. This is Michael Chandler and Charles Oliveira. If you’ve watched their fights, you know that they aren’t always guided by logical decision-making. These two aren’t who they are because they fight with restraint and calculation. This is a two true outcome fight if there ever was one.

That’s why UFC made it; why everyone wants to see it; why no one’s batting an eye at it. In a week of debate over the meritocratic fallacy underlying UFC 309’s main event, no one’s considering how this fight isn’t particularly congruous within its division, either. It makes sense as a fun fight. And sometimes that’s all a fight has to be.

“I'm a guy who wants to lay all my chips on the table at times. I'm not afraid to lay all my chips on the table and bet on myself,” Chandler said. “And Charles will fight anybody. I realize the man I'm up against. I realize the danger he poses. … Charles Oliveira is the perfect opponent for me. It is the perfect time. You could not have scripted it any better.”