UFC 299 roundtable: Does Sean O’Malley move on to superfights if he gets past Marlon Vera?

UFC 299 is headlined by Sean O’Malley defending his bantamweight title for the first time. And maybe the last?

It’s not far-fetched to see a world where O’Malley defeats rival Marlon Vera and then immediately follows in Conor McGregor’s footsteps, eschewing his divisional responsibilities to pursue “champ-champ” status or cross over to boxing. Some of the biggest names looking to get a piece of “Sugar” aren’t in his division — or MMA at all, for that matter.

With one of the most stacked pay-per-views of the year just days away, MMA Fighting’s Alexander K. Lee, Mike Heck, and Jed Meshew ponder O’Malley’s future and which fighters have the most to gain with an impressive performance in Miami this Saturday.

1. Will Sean O’Malley look beyond the UFC bantamweight roster for his next challenge?

Lee: I’ll admit, my eyes rolled along with pretty much everyone else’s when Sean O’Malley started drumming up some nonsense about fighting Gervonta Davis. He had just won the UFC bantamweight title and the last thing anyone wanted to hear is him hunting for a fight with a boxing champion.

But this recent Ryan Garcia drama? I’m kinda here for it.

ICYMI, “King Ryan” recently boasted on The MMA Hour that he “will destroy” O’Malley in a UFC fight. That’s right, he didn’t call for O’Malley to step into the ring with him, he essentially did the “six months of sprawl training” meme but in real life and stated that with three or four months to prepare, he could take O’Malley out in his MMA debut. Unhinged, but I’m intrigued.

If there’s any truth to this — and Garcia claims that he already sent out feelers to Dana White, make of that what you wil l— then how can the UFC resist throwing together such a wacky crossover fight? It’s been more than 13 years since James Toney embarrassed himself against Randy Couture. Isn’t it time to give another boxer the chance to follow in his footsteps?

I sincerely doubt that Garcia can present a realistic challenge to O’Malley in MMA, but I’d pay good money to see how he reacts to O’Malley throwing a spinning kick at his noggin. Make it happen, people.

UFC 2024 Seasonal Press Conference — Sean O’Malley

Heck: My eyes are still rolling when it comes to the Ryan Garcia idea, but that doesn’t mean it can’t happen. It won’t, because I think the stars would align for a different fight that I wouldn’t be wholly interested in because of the work that needs to be done by both guys in their own divisions. That being said, if the UFC is going to Spain, they’d be hard pressed to find a bigger fight to fill a stadium than putting Ilia Topuria in there with O’Malley.

I know, I know, I can see it now, “Mike, you’re staunchly against the champ vs. champ stuff without cleaning out a division,” and you would be correct. But the UFC certainly doesn’t think like that, and by tapping into this huge market, the UFC sees dollar signs everywhere. Personally, I hate it. Topuria has a lot of people to fight — a rematch with Alexander Volkanovski, Movsar Evloev, Brian Ortega, Yair Rodriguez, the list goes on — and so does O’Malley. You only get one chance to make a first impression, and I think Topuria wants to make the biggest impression he can in his home country. O’Malley is saying the right things lately, but if Joe Rogan hands off that live microphone after a highlight-reel O’Malley win, I can see the callout for Topuria and a shot a second belt.

Meshew: If you had asked me this question four months ago, I’d have said there is no chance that O’Malley fights Merab Dvalishvili. (Mike) Heck, if you had asked me it a few weeks ago, I’d have said the same. But then a funny thing happened in February: Dvalishvili got over.

By beating Henry Cejudo at UFC 298 (and then having an hour-long post-fight interview), Dvalishvili did the impossible and cemented himself as not only the most deserving next title challenger, but somehow the one with the most support. Fans have rallied behind Dvalishvili such that even O’Malley himself — who previously said he wanted Ilia Topuria next — has come out and said Merab is next. It’s an improbable turn of events, but a welcome one as the bulk of the MMA fan base is finally realizing that champ-champ fights should be special and not the norm, and O’Malley comes to terms with the idea that he’s not the next Conor McGregor.

Of course, this entire question hinges on the idea that O’Malley actually beats Chito Vera on Saturday, and I have to tell you, I have serious doubts about that happening. Fortunately, even if Chito wins, the outcome remains the same: Dvalishvili is next in line and Georgia will continue to have a stellar 2024.

2. Outside of the headliner, what main card fighter has the most to gain?

Meshew: There might be more obvious answers available, but give me Song Yadong, because of all the other fights on this main card, Song is the only person fighting a former undisputed UFC champion.

Still only 26 years old, Song is an incredibly exciting Chinese fighter competing in one of the sport’s best weight classes. That’s a promotional unicorn right there. And while he does have a loss to Cory Sandhagen on the résumé, losses mean less in MMA these days. If Song comes in and gets a win over Petr Yan on Saturday, that gets him a top-five ranking in the UFC and immediately puts him in the title conversation. At minimum, a win gets him a title eliminator, and if he’s lucky, maybe he somehow sneaks into a backup fighter role for the next bantamweight title fight. Crazier things have happened.

On the other side of things, a loss is truly catastrophic for Yan. Three years ago people thought Yan would be the guy to actually have a long reign at bantamweight. Then the Aljamain Sterling fiasco happened and now Yan has lost four of five. One illegal knee ruined his career, and if Yan loses Saturday, it may well end it. The history of MMA fighters who have lost four in a row and then rebounded to have any level of success is exceedingly small, and none of them have gone on to claim (or reclaim) gold. Yan has everything to lose this weekend.

Lee: If we’re talking about fighters who can boost their stock the most, then we’re talking about the hottest fighter in the UFC’s lightweight division: Benoit Saint Denis.

It’s crazy to think that Saint Denis has been fighting professionally for just five years and that his first UFC fight — a short-notice welterweight booking against Elizeu Zaleski dos Santos — was most notable for the amount of punishment that the Frenchman took before somehow surviving to the cards. Few could have guessed that he’d go on a hellacious win streak that could be capped off by a win over one of the most respected warriors of his generation.

All the respect in the world for Poirier taking this fight, because he’s giving Saint Denis the opportunity to make a name off of him. Poirier might see this as a winnable fight, and why shouldn’t he, but he has to know that he’s stepping into the octagon with a rising contender who has trucked his past five opponents and has all the makings of a future champion. Once upon a time, Poirier was a white-hot prospect destined for UFC glory; now, it’s his job to slow Saint Denis’ ascent.

Saint Denis won’t get a title shot if he smokes Poirier, but it will put him on the short list and unquestionably move him into a different echelon at 155 pounds. Don’t be surprised if we look back on this fight as the moment that Saint Denis cemented himself as belonging among the very best in the division.

Heck: I respect both answers tremendously, gentlemen, but the correct answer is Michael Page, who faces Kevin Holland in his first octagon appearance. Many have wondered how “MVP” would fare in the UFC, and Holland is the perfect first test.

While the UFC completely bungled announcing the signing of Page, it has made a huge effort to make things right since with some excellent promos. The timing could not be better for this debut, especially since the UFC has made the U.K. a spot they travel to at least once a year. And with a U.K. fighter holding the welterweight title in Leon Edwards, there’s no doubt those Tuesday matchmaking meetings have featured many conversations about building to a fight between Edwards and Page if he’s able to knock off Holland, which will be no easy feat.

And even though this shouldn’t be the case, Belal Muhammad should be heading into UFC 299 fight week being the biggest Kevin Holland fan on the planet, and we all know why. If “MVP” runs over Holland, Dana White and the decision makers will certainly consider having Page jump the line.

3. Can the Curtis Blaydes vs. Jailton Almeida winner sneak into a title shot?

Heck: If the question was just about Jailton Almeida, than the answer is unequivocally yes. As I’ve said many times on multiple shows, if Almeida makes quick work of Curtis Blaydes, I can see the UFC booking Tom Aspinall’s first interim title defense against Almeida in the main event of UFC 301. That card is going to need a main event that can draw the eyeballs of the fan base as a whole, and while I think Alexandre Pantoja is the freaking man, the UFC loves them some heavyweight headliners. That fight is intriguing as hell.

Now, for Blaydes, I’m not so sure. Aspinall could want that fight because their first meeting ended in such a weird way, but the UFC hasn’t seemed to be in the “give Curtis Blaydes a title shot” business, no matter what he does. If Blaydes wins, I think Ciryl Gane would get the shot at Aspinall.

And no matter what happens, neither will be fighting Jon Jones.

Meshew: If by “title shot” you mean “interim title (but we all view it as the true belt because Jones is a scared little ninny who don’t want that Aspinall smoke) shot,” then yes. Absolutely.

As Mike noted, in a dream scenario for the UFC, Almeida finishes Curtis Blaydes and then boom, Aspinall vs. Almeida for the interim strap can headline UFC 301 and the return to Brazil. If Blaydes wins, that’s a less appealing location, but the fight itself is still excellent as these two have unfinished business, what with Aspinall blowing out his knee four seconds into their fight. Now Blaydes and Aspinall could run it back for gold. Whether that fight would go to Brazil, I’m not sure about, but it seems very clear that the winner of this matchup will be the next guy to fight the true heavyweight champion, Aspinall.

UFC Fight Night: Almeida v Lewis — Jailton Almeida

Lee: My only qualm with this question is the word “sneak,” because Almeida shouldn’t be sneaking into anything. With his dominant grappling, he should be at the forefront of the conversation!

No, his five-round smothering of Derrick Lewis wasn’t exactly the statement he needed to make to prove he’s the heavyweight division’s No. 1 contender, but just a glance at his overall body of work should be enough to remind people that he’s a destroyer of worlds when the fight hits the mat. That singular skill makes him a threat to whoever holds the title when he comes knocking on that door, be it Aspinall or Jones.

The good news for Almeida stans such as myself is that the matchmakers did the right thing and re-booked this matchup with Blaydes. A win over Blaydes will answer a lot of questions, no matter how he gets it done, and once the drama at the top of the division is resolved, the timing should be perfect for Almeida to slide into his well-earned championship opportunity.

4. What’s the most intriguing storyline from the rest of a stacked preliminary card?

Lee: This story is definitely flying under the radar, so if I have to be the one point a neon arrow in its direction, I’m happy to do it.

Is this the last fight for Joanne Wood?

The former Joanne Calderwood — really, known to the masses as just “JoJo” — recently hinted that her preliminary opening bout against Maryna Moroz could be her “last one.” If that’s the case, the fight marks the end of a 12-year career that saw the soft-spoken Scotswoman emerge as a contender in both Invicta FC and the UFC and nearly challenge Valentina Shevchenko for a flyweight title, a booking that was spoiled by a Shevchenko injury and then lost when Wood dropped a short-notice, stay-busy fight to Jennifer Maia.

Though she never captured a belt, Wood helped to build the women’s 115- and 125-pound divisions in the UFC and consistently threw her name in the hat with the best, including Alexa Grasso, Lauren Murphy, and Jessica Andrade. Kudos to the matchmakers for setting up this rematch with Moroz, giving Wood the chance to avenge an upset loss early in her UFC career.

The UFC Hall of Fame is unlikely to come calling for Wood in the future, which makes it all the more important that we appreciate her contributions to a business that is all too quick to forget. We appreciate you, JoJo.

Heck: The first thing that popped into my head was Maycee Barber’s opportunity to prove she’s a top-five talent at 125 pounds against perennial litmus test Katlyn Cerminara (formerly Chookagian), but you know how much I like to see a viral regional sensation with freakish size and attributes come in and try to perform under the bright lights. So my pick is Josh Parisian welcoming Robelis Despaigne to the UFC.

Despaigne is a 6-foot-7 massive heavyweight who just melts people — 4-0, four first-round finishes, and his last three fights have lasted a combined 19 seconds. This dude is a monster, but he’s getting his first real veteran test, and if Parisian can come in with a granite chin and grapples like he’s never grappled before, it could get interesting. Still, the UFC matchmakers typically have an eye for these kinds of things, so I can certainly see “The Big Boy” getting a huge rise in stock on Saturday.

Meshew: It has to be Mateusz Gamrot and the totally muddled lightweight title picture.

As things stand right this second, Islam Makhachev has no obvious contender for his lightweight belt. The widely held belief is that Makhachev will defend his title in June at the Saudi Arabia card, but who the (Mike) Heck will it be against? Everyone thought it would be Justin Gaethje — he and Max Holloway are about to beat the souls out of each other at UFC 300. Charles Oliveira was the other obvious choice — he’s fighting Arman Tsarukyan at UFC 300. The chances of any of those guys coming out of 300 healthy enough to turn around and fight in June feels really slim.

OK, but he has to fight someone. What’s Dustin Poirier doing? Oh, that’s right, he and Saint Denis are going to bash each other’s brains in at Saturday’s co-main event. It’s unlikely either of them is making a quick turnaround. Michael Chandler is still out there desperately hoping for Conor McGregor’s grace, so he’s gone. That leaves Gamrot as the only viable option. He was the backup fighter for UFC 294, and as much as we all respect Rafael dos Anjos, his best days are behind him. Gamrot should come out of Saturday with a good name on the résumé, good health, and the inside track towards getting the title fight he deserved to get at UFC 294.*

*I tried to tell you all that it was stupid to run back Makhachev vs. Volkanovski on 10 days notice, but everyone called me a hater. Then it turns out Volk was in no shape to make a legitimate effort at winning; instead, he got run over and then got lit up by Ilia Topuria a few months. All the while, Gamrot — who is a fun fighter! — was right there and prepared to step in. The lesson, as always, is I’m always right.