Prime Picks: UFC Fight Night 176 ‘Overeem vs. Sakai’

Sign up for ESPN+ right here, and you can then stream the UFC live on your smart TV, computer, phone, tablet or streaming device via the ESPN app.

The Ultimate Fighting Championship on Saturday continues the marathon of events at the UFC Apex in Las Vegas with an intentionally shorter offering topped by an important heavyweight pairing. Almost all of the matchups at UFC Fight Night 176 are close on the books, with only two favorites posting odds above -175. These lines allow for some excellent opportunities to come out ahead, as you will discover in this edition of Prime Picks.

Alistair Overeem (-160)

Overeem finds himself in the unenviable position of taking on a rising prospect—one who is far younger at almost exactly 11 years—in the division, as he looks to hold the line and stay at the top echelon of the weight class. These types of matchups can bode poorly for the aging fighter, as the youthful contender looks to make his name on the back of an old lion. Even though Overeem has been on the losing end more than most, a win for Sakai would represent the biggest feather in his cap against by far his most dangerous opponent. While Sakai is a fundamentally sound fighter who does not fight like most heavyweights by wildly pursuing knockouts, we anticipate Overeem being too stiff of a test for him.

Overeem has struggled for most of his career against power strikers who can put him down with single shots, cracking the chin that has been battle-tested more than most. Fourteen defeats by knockout may serve as the prelude to the 15th at the hands of Sakai, but the Brazilian does not crack like the men who have put out “The Demolition Man” since joining the UFC roster. Instead, the Dana White's Contender Series graduate puts volume on his opponents until they wilt under pressure. This was on display against Chase Sherman and in his surprisingly quick stoppage against Marcin Tybura nearly a year ago.

A kickboxer who loves the clinch, Overeem may welcome Sakai punching his way into a close grappling position. From there, Overeem can deliver the lethal knees to the midsection that have felled many a man over the years. If there is a somewhat surprising development throughout the Dutchman’s career, it is that he maintains a sneaky takedown game that he can use to get on top and batter his opponents. Such a strategy allowed him to hand Sergei Pavlovich his first career defeat in 2018. The striking is still on point for Overeem, as evidenced by the manner in which he put down Walt Harris with a head kick and a plethora of follow-up punches in May.

Overeem is dangerous enough to end the fight at any time, but it is entirely possible that Sakai outlasts him by taking the later rounds. In Overeem’s 65-fight MMA career, he has only fought beyond the third round once, and he was on his way to likely taking a decision before Jairzinho Rozenstruik struck. Unless Overeem has finally hit his age cliff and we see a serious deterioration in his ability to put shin to chin, “The Demolition Man” appears to still have enough in the tank to stave off the streaking Sakai. Although Sakai has won all four of his bouts inside the Octagon, his decisions were mired in controversy, especially in his win over a 2019 version of Andrei Arlovski. If every scoring media member awarded the fight to Arlovski, Sakai might be out of his depth here. Should you expect that Overeem can not only win but secure a stoppage, that line is a palatable +130.

Ovince St. Preux (+110)

This bout was originally scheduled for UFC on ESPN 15 two weeks prior, and other than the psychological effect on a fighter over his bout being scratched on fight week, little appears to have changed. Therefore, the same reasoning behind the previous analysis applies in full. Although St. Preux is ever so slightly more of an underdog than before, the line will likely return to what it ended at before the fight was pulled.

It seems to be almost a foregone conclusion at this point that St. Preux will drop the first round badly, only to come out of his corner in the second frame to try to mount a comeback. On multiple occasions, he has done so by allowing his opponent to punch himself out while trying to secure a stoppage. The knockout-minded Alonzo Menifield will likely take the same approach, with none of his career wins coming later than 32 seconds into the second stanza. While it is entirely possible that Menifield busts up this play by smashing out “OSP,” we believe the former University of Tennessee linebacker can ride out the early storm and get his hand raised.

In Menifield’s most recent appearance, many flaws were exposed when his cardio waned after the opening round. Devin Clark rode through a busted eye and a lot of damage by keeping his volume high enough to stave off the advancing, then-unbeaten prospect. A wealth of takedown attempts—all but one was stuffed—contributed to Menifield’s fatigue level, and “OSP” could very easily follow that path to press his smaller opponent to the cage and try to trip him to the floor. Although Menifield sports knockout victories inside the Octagon over Vinicius Moreira Castro and Paul Craig, St. Preux’s chin has historically held up better than either of those light heavyweights.

Unless Menifield catches St. Preux early, it will likely be a long night for the Texan. Even though “OSP” takes damage often in his bouts, it is quite difficult to finish him with strikes alone. The only men to do so are Virgil Zwicker over a decade ago and Jimi Manuwa, who cut him down with a pair of blistering hooks in 2016. Although Menifield has the power to become the third, he may find that he has hit a wall and not know what to do when he hits his man with everything in his arsenal, only to find his opponent still standing. Menifield will be putting himself in prime position if he scores a victory over the former title challenger, as he likely fell upwards into this matchup against a fringe Top 15 light heavyweight after his loss to Clark. We expect that once Hurricane Menifield has run its course, a measured St. Preux can get the job done. If one is feeling especially bold, St. Preux by Submission is a decent +250. Perhaps “OSP” goes after his patented Von Preux choke if Menifield falls to his back and absently fishes for a guillotine choke.

Michel Pereira (-115)

For a wild, unpredictable attacker like Pereira, perhaps the best thing the promotion can do is match him against another fighter that poses a similar style. Zelim Imadaev will not likely take the fight down like Tristan Connelly managed to do, nor is he a crafty veteran like Diego Sanchez. Instead, the Russian with a 100 percent knockout rate across his wins—including a spinning elbow knockout and a stoppage in 13 seconds to earn a UFC contract—will almost certainly toe the line with “Demolidor.” This may be his undoing, as Danny Roberts already cracked Imadaev’s chin in November, and Pereira shut out Roberts’ lights in under two minutes in his promotional debut.

A very reasonable prop bet of the fight ending within 1.5 rounds is currently +130, with six of eight wins for Imadaev coming in that stretch compared to upwards of 15 for the Brazilian. Like two bulls, these two welterweight strikers will likely clash together until one of them falls. Although both men only sport a single knockout defeat on their record, this matchup has all the makings of giving one of them their second in dramatic fashion. If the over/under of specific rounds is a little daunting, a safer option is Fight Doesn’t Go to Decision at -180.

This bout is currently a pick-’em, with the comeback of Imadaev at -105. It would not be surprising if a slightly more composed Imadaev clips the high-flier after he leaps in the air or springs off the fence. The gas tank is likely going to be the biggest opponent for these two men, and the most dangerous round will unquestionably be the first. We expect that Imadaev’s aggression will play right into Pereira’s hands, feet, knees and elbows. If the fight gets out of the opening frame, an Imadaev pick might look wise, but Pereira hits hard enough that he will likely be able to force a stoppage early.

Kevin Natividad (+195)

As far as late replacements go, the promotion could do far worse than a heavy-handed striker like Natividad. “Quicksand” will step in for Ricky Simon, who was forced to bow out of the match against Brian Kelleher when a cornerman tested positive for COVID-19. An Arizona Combat Sports rep, Natividad last competed in July, when he starched Kyle Estrada in the second frame. Other than an unsuspecting nine-second bludgeoning at the hands of Glen Baker in his Legacy Fighting Alliance debut, much can be said about the 27-year-old prospect. His hard-charging style may give the fellow brawler fits in the early going and could allow him to spring the upset.

Kelleher can take a punch, and the New York native’s chin has held up for the most part despite his testing it frequently since his promotional debut in 2017. The only one to put him down with strikes was the bomb-chucking John Lineker, as the UFC ex-pat beat him to the punch and stuffed takedowns to set up a one-hitter-quitter left hook in the third round. Although Natividad might be a far cry from the sledgehammer that is Lineker, he has a similar style and loves to get in the pocket and trade. Backing up his slugger style are solid wrestling chops that can both defend against and fight for takedowns. Although he may not be able to ground Kelleher—only three have in the UFC to date—he can keep “Boom” honest and sprawl if he lands on him and forces a shot.

The Hawaiian’s aggression might play against him in his debut on short notice, as his cardio mixed in with his style may not be able to go 15 minutes at this point. Natividad might have to hope for an early stoppage, as Kelleher can hang in there to the bitter end. Exploiting Kelleher’s historically weaker submission defense may not be in Natividad’s wheelhouse, but a situation could certainly arise where he hurts Kelleher on the feet before the New Yorker shoots in and finds himself in submission danger. We expect that Natividad will prefer to get this done with his powerful boxing, and if he does not, he should be able to take the first round and push through the second to survive the last frame and get his hand raised. Kelleher, who holds several wins in the third round, could possibly surge in Round 3. It would be up to Natividad to either get the fight done before then or ride out the storm to earn the upset.