Prime Picks: UFC 299 ‘O’Malley vs. Vera 2’

The Ultimate Fighting Championship goes all out in Miami for what might be on paper the best pure MMA card of the year regardless of promotion. Of the 14 bouts on the monster lineup, eight could easily serve as the headliner of any UFC show. Underdogs are poised to spring some mighty but foreseeable upsets across the lineup, and plenty of money can be made. Join the UFC 299 edition of Prime Picks as we expect one heavyweight will show there are levels to this game, balk at the favored two in the marquee matches and go bowling for options on the undercard.

STRAIGHT-UP CASH

Curtis Blaydes (-105)

When looking at the lineup of favorites on UFC 299—Sean O'Malley, Benoit St. Denis, Kevin Holland, Jack Della Maddalena and Petr Yan—who sounds most like a lock? If your answer is any of those names, your confidence is much higher than most. Instead, we dip to the preliminary headliner, with a heavyweight match that could headline any UFC Fight Night event. To the surprise of some, Blaydes is not even the odds-on favorite, as the two are technically in a pick’em, although his foe, Jailton Almeida, is above him at -115. This grappler-on-grappler violence should be a rude awakening for the Brazilian, who will likely find out very quickly he cannot ragdoll Blaydes as he has other opponents in the past.

In his 17-fight UFC tenure, the number of men to land takedowns on Blaydes is exactly two: Alexander Volkov and Cody East. The former occurred during a division-leading 14-takedown effort against Volkov, while the latter came early in Blaydes’ career in a bout that he won by smashing East’s face off with ground-and-pound. There is no blueprint for success when grappling against Blaydes, and Almeida will certainly try to forge new territory. While the totals are limited, few big men have even bothered trying, knowing they will hit the 6-foot-4 stone wall in the junior college national champ at Harper College. At heavyweight, that is more than enough to shut anyone else down.

Questions about the Brazilian’s cardio were partially answered when he went five rounds with Derrick Lewis, but it is hardly draining when the lumbering “Black Beast” only lands on you 20 times in 25 minutes. B.J. Penn famously possessed soul-crushing energy reserves where he could destroy the likes of Kenny Florian or Diego Sanchez and procure late stoppages. However, when the tables were turned against him, a la Georges St. Pierre in their rematch, the lightweight great suddenly ran out of gas. When Almeida is on cruise control, hanging on and smacking his foes or searching for submissions, he can do that all day. On the other hand, what happens when Blaydes stuffs his first, second and third takedowns? Blaydes hits substantially harder, and Almeida is not known for his prowess on the feet. This is his party to ruin unless we see something never before displayed against him.

STRAIGHT-UP PASS

Benoit St. Denis (-215)

Much can change in a year or less. In July 2023, St. Denis was a substantial underdog to Ismael Bonfim at some card at the UFC Apex, while Dustin Poirier closed as the betting favorite against Justin Gaethje in the headliner of UFC 291. Poirier succumbed to a head kick, and St. Denis has rattled off three stoppages, which leads the latter into his favored status in this five-round non-title co-headliner. Much like how Gaethje had to defend his place high on the rankings in his encounter against Rafael Fiziev, Poirier is tangling with the Frenchman. For reference, Poirier (+170) has not been this high in terms of plus money when not fighting for a title or in main events since his match with Conor McGregor in 2014. There are much better options than the moneyline on “God of War” on this lineup.

Poirier was very close to taking the “Dog Will Hunt” portion of this event, and that segment was also nearly transformed into “dogs” plural to add Poirier and at least one other name to the list. Instead, we keep our four betting categories to the standard pay-per-view form. St. Denis has developed his striking by leaps and bounds lately, with three of his four career knockouts coming in the last two years. It is still wild, open and porous but powerful, and he leaves plenty of opportunities to be countered. Poirier can and will take advantage of any of these moments, and Poirier’s excellence as a grappler cannot be dismissed. “The Diamond” may have been submitted twice in the last five years, but they were performed by the UFC’s all-time submission leader Charles Oliveira and the dominant Khabib Nurmagomedov. St. Denis might be a star on the rise, but this looks like a “too much, too soon” pairing to leap from Matt Frevola to here.

DOG WILL HUNT

Marlon Vera (+225)

For starters, Vera already holds a non-controversial victory over champion O’Malley. His strategy for victory was replicated by Pedro Munhoz, who exclusively threw and landed leg kicks that were having an impact until O’Malley lanced the Brazilian’s eyeball with an outstretched finger. Since that meeting, O’Malley has not tasted defeat, although most considered his split decision win over Petr Yan a “Robbery of the Year” frontrunner in 2022. For reference, on fight day, every single scoring media member handed in cards for Yan, amounting to 26 scores in his favor to zero for O’Malley; the lone dissenting media member changed his score days later after watching it again, which is not how these scores are registered or tabulated. Vera is a huge underdog and that should not be the case in the cage, no matter how much better O’Malley has become in the last three-plus years.

“Chito” remains in his athletic prime in this rematch, and he is just as durable and heavy-handed as ever. His overall skill set may not have changed since the first fight, but he has found ways of putting power behind strikes that may not have been there as much before. In addition to dropping Rob Font and Dominick Cruz a combined six times, Vera was able to keep it close despite Sandhagen more than doubling him up on significant strike totals because of his sheer firepower. Vera still starts relatively slowly, and he cannot help but find himself in a slugfest, where he is outstruck in raw numbers but hits that much harder. A Vera that gets into a reckless brawl may get popped by O’Malley, but O’Malley prefers to snipe rather than trade leather. The iron-chinned live dog in “Chito” can push the pace, chop down the lead legs and keep O’Malley honest with his surprisingly accurate big shots to pick up another win.

AN ACCUMULATION CONTEMPLATION:

Katlyn Cerminara-Maycee Barber Lasts Over 2.5 Rounds (-410)

Mateusz Gamrot (-455)

Robelis Despaigne-Josh Parisian Lasts Under 1.5 Rounds (-260)

TOTAL ODDS: +110

Not many moneylines merit parlay consideration due to the serious risks of the matchups, and several of the favorites in the -200 range face opponents with clear and reasonable paths to victory. Chalk may win out, but who would be surprised if Vera chopped down O’Malley again or Poirier snagged St. Denis in a sneaky brabo choke? Instead, we go to a relative given: Cerminara goes to a decision. In the entire UFC run for the woman formerly known as Chookagian, only two fights have ended inside the distance. Valentina Shevchenko and Jessica Andrade put her away with strikes, and Barber will try as hard as she can to do the same. She will have to get inside to do so, as the taller, longer Cerminara stays at the end of her jab and front kick to kickbox her way to victory. With Cerminara’s underrated ground game and distant striking approach, the two will likely be in the cage for an extended time.

The sole pick we confidently make is former two-division KSW king Gamrot against 39-year-old ex-UFC champ Rafael dos Anjos. While a decent enough striker, he rarely lets it be a liability; dos Anjos’ success or failure largely depends on his wrestling. It might be a bit of an oversimplification to say that when he maintains the takedown and control advantage, he wins, but when he does not, he loses, but it is not far off from the truth. For example, foes like Kamaru Usman, Colby Covington, Michael Chiesa and even his last test of Vicente Luque had their way with him on the mat. On the other hand, Bryan Barberena, Renato Carneiro and Paul Felder could not get him off of them, whether on the ground or in a clinch, and he prevailed. Gamrot, on paper, has the superior skill set in this area, both in terms of getting the fight down and with his anti-wrestling, making him a good option in a parlay with his overall line a bit heavy for a single play.

Despaigne needed 19 seconds to wipe out three adversaries in his last three fights. The taekwondo specialist maintains a reach that surpasses Jon Jones and Stefan Struve, and he has used it well so far in his burgeoning MMA career. It remains to be seen how Despaigne will fare against an opponent with a pulse, as his first four foes combined for a record of 1-0. Luckily for Despaigne, he draws a fellow striker in Parisian, who is not afraid of throwing hands even if it is to his detriment. If Parisian absorbs shots he does not like, he is capable of closing distance and securing takedowns. Finagling the massive Cuban to the mat would be an undertaking while removing his best weapons. One way or another, this fight will end by stoppage, and it will not likely take long for it to happen.