Parlaying and Praying: UFC Fight Night 149 ‘Overeem vs. Oleynik’

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UFC Fight Night 149 on Saturday marks the Ultimate Fighting Championship’s second card in Russia after nearly 26 years in business. What is truly remarkable is that the event is brought to us in partnership with M-1 Global. Who would have ever bet on that?

Yes, in conjunction with M-1 Global and Russian-Chinese investment fund Mubadala Investment Company, the UFC is headed to the Yubileyny Sports Complex in St. Petersburg. This comes a decade after the promotion failed to sign former M-1 star Fedor Emelianenko and then attempted to buy the company outright. Fast forward 10 years and the MMA landscape is a vastly different one, creating some unexpected bedfellows. Not everything is unfamiliar, though, as our headliner features well-known veteran heavyweights Alistair Overeem and Alexey Oleynik, as they top a card replete with talent from Russia and the Commonwealth of Independent States.

This event may prove a tricky one on which to bet. Almost a third of the 22 fighters on the card are making their Octagon debuts; most of the known quantities on the bill are stern favorites; and those who are not are in some iffy, volatile matchups. However, we need to take this opportunity to get right. After all, the only main card fight I predicted correctly at UFC 236 was Israel Adesanya’s win over Kelvin Gastelum, and that was the fight I cautioned bettors to avoid.

The only way to go is up, so let’s figure out how to make some blini and borscht off of the UFC Fight Night 149 soiree in St. Petersburg:

Straight Up Cash

Alistair Overeem (-240)

So many thoughts here. First of all, it naturally makes me queasy having a section called “Straight Up Cash” and featuring Overeem within it, especially a 38-year-old incarnation of the Dutchman. However, I will repeat a familiar refrain of mine: When it comes to this portion of the column, I always try to feature an event’s main event or co-feature, because frankly, that’s why people read articles like this and in practice, the most important, marquee bouts are those that people prefer to bet on and attract the lion’s share of betting tickets. UFC Fight Night 149 is a card without a classic, proper co-headliner, so here we are.

Overeem turns 39 next month, and he has been fighting professionally for 20 years. Even at his best, we know he’s fallible and prone to gaffes that often send him from the brink of victory into the torment of brutal defeat. With that being said, he’s in a fairly insulated position facing Oleynik, and given the style matchup, I don’t think that -240 is the worst number in the world. In fact, if not for Overeem’s age and durability history, he’d probably be -300 or above. Plus, Overeem has the benefit of having trained with “The Boa Constrictor” in the past and knowing what the Ukrainian-born Russian brings to the table.

The 41-year-old Oleynik may have some surprising pop in his hands when he can land, but 45 of his 57 wins have come with proper submission holds, notably his infamous Ezekiel choke. Oleynik is not a great takedown artist, typically standing flat-footed and then throwing a barrage of punches to rush into the clinch, where he can toss his opponents to the canvas and get to work. This seems like a pretty miserable strategy against Overeem, who should be able to liberally leg kick and combination punch from range, and when “The Boa Constrictor” rushes inside, he figures to be met with brutal knees. “Ubereem” has always been an incredibly underrated clinch grappler, on top of his potent striking ability in close.

In Oleynik, we’re talking about a fighter who had a world of problems in the standup with Daniel Omielanczuk and Curtis Blaydes, so he should prove easy fodder for Overeem without the serious threat of cracking the Dutchman’s chin. On top of that, Overeem by knockout is listed at -155, which is worth pairing with a straight-up bet on the former K-1 World Grand Prix winner.

Straight Up Pass

Alexander Yakovlev (-150)-Alex da Silva Coelho (+120)

There aren’t a ton of especially competitive betting lines on this card, so I can see how a bettor on either side of the fence could be enticed by these numbers. However, I see this fight as a bit of a mess for a couple of reasons and would rather save my dollars.

I’m happy to see Yakovlev returning to 155 pounds where he belongs, and perhaps he’ll even enjoy a boost fighting in his adopted backyard of St. Petersburg. However, we’re still talking about a fighter who went 1-4 in the Octagon as a welterweight, and while it’s worth noting that he faced pretty stout competition in Demian Maia and Kamaru Usman within the division, it’s important to realize that there is really nothing spectacular about Yakovlev’s game. In fact, his only two UFC wins came by quickly popping the mediocre George Sullivan and riding out a 15-minute division over a completely shot Gray Maynard. Russia’s favorite fighter-stroke-rapper is mildly well-rounded, but he is just a straightforward wrestler at heart, and outside of the faded Maynard, he has lost to every single notable fighter he has faced other than Paul Daley five and a half years ago.

On the flipside, we have Coelho, who has racked up a gaudy 20-1 record but has largely done so by feasting on underskilled opposition while fighting for Aspera Fighting Championship -- an organization promoted by his own gym, Astra Fight Team. The 23-year-old “Leko” is the far more dynamic commodity, having finished off all 20 of his pro victims, but despite his nasty low kicks and combination punching, he has shown some pretty flimsy takedown defense that could land him underneath Yakovlev for long periods of time.

Has Coelho shored up his takedown defense? Can he scramble or sweep to top position? Can he damage the plodding Russian on the feet? We have one unspectacular fighter with a wrestling advantage against a weak wrestler with vastly superior standup who has feasted largely on cans. If we go the full 15 minutes, who knows what the judges might see. I’m intrigued to see how it unfolds, but I’m not opening the billfold on this one.

A Prop-ular Bet

Islam Makhachev-Arman Tsarukyan Goes to Decision (-105)

After all the confusion surrounding Makhachev’s booking -- or non-booking, if you believe him -- against Francisco Trinaldo several months ago and his role in the infamous Khabib Nurmagomedov-Conor McGregor brawl at UFC 229, I’m excited to see the once-beaten Dagestan native back in action. Likewise, I’m enthusiastic about the UFC signing another once-beaten fighter in 22-year-old Armenian Arman Tsarukyan to get a better read on his potential. This is an intriguing pairing of prospects, but having said that, their styles may have a negating effect on one another, making this prop an interesting and worthwhile play to me.

Tsarukyan is a total package. He’s a hard-nosed wrestler by trade with strong chain wrestling, and he is especially clever at timing and baiting his opponents into falling into his power double-leg takedowns. More than that, he’s a good submission finisher and has polished his striking recently, showing nifty head movement to set up boxing combinations and some great kicking offense, as shown when he went took out Brazilian veteran Felipe Olivieri’s head. Apart from a 30-second knockout loss early in his career when he got caught cold, he has basically been large and in charge against all of his opponents, start to finish.

Similarly, the only misstep in Makhachev’s career -- Nurmagomedov-McGregor brawl involvement aside -- was when was similarly caught early by the mercurial Adriano Martins in under two minutes in a fight he would win nine times out of 10. The sticking point for me here is that while I favor Makhachev -- I think he is one of the most underrated talents on UFC roster -- he is a low-output fighter on the feet who prefers to work a mauling style on the floor to set up submission opportunities. He is not a lockdown control artist on the canvas but rather a diligent, consistent attacker, using constant takedowns and positional advancement to wear down foes and look for the finish. He is incredibly buttoned up on the feet; his 0.82 significant strikes absorbed per minute is the lowest rate in UFC history. While Tsarukyan is unlikely to be able to use his technical, developing standup to dominate the place and pace of the bout, Makhachev may also struggle to get consistent takedowns or secure dominant positions as easily as he has against other opponents.

Again, I like the more experienced Makhachev, and I think he’ll give the upstart Tsarukyan a necessary growth experience as a prospect. However, I think Makhachev may have to spend more time standing and blocking shots from the Armenia native, and his efforts on the ground may force him to play position over taking too many risks against a strong grappler. I’ll take the points to get to the pay window.

An Unprop-ular Bet

Shamil Abdurakhimov-Marcin Tybura Does Not Go to Decision (+130)

We’ve discussed this dynamic before: Since roughly 75 percent of UFC heavyweight fights don’t reach the scorecards and the division tends to be less talented than others, there’s a natural tendency to imagine that within a 15-minute window, in any pairing of heavyweights, someone is going to slip up, get clobbered on the feet, fall into a submission or simply gas out and get pounded on. With Abdurakhimov and Tybura, I think we’re in for a slough -- and one that will require the judges.

Both fighters share some similar traits despite different backgrounds. Abdurakhimov is primarily a striker with a deep sanshou background, and it was through his standup that he earned most of his early career wins. However, as time has gone on, he has relied more and more on his wrestling. While he has a clever lead left hook and often uses smart feints to set up his heavy right hands, he’s a low-output striker, landing only 2.44 significant strikes per minute during his UFC tenure. He isn’t much of a cardio specimen, and perhaps as a control mechanism, he often employs long, aimless clinches when he cannot buy easy takedowns. His last outing, a prosaic win over a faded Andrei Arlovski, is highly emblematic of his style.

Meanwhile, Tybura, a Brazilian jiu-jitsu black belt, has worked diligently to improve his striking during his Octagon tenure, as once he reached the UFC, it became apparent he could not simply get easy clinch takedowns and dominate opponents on the floor as easily as he did while rising through the European scene. While he went back to his heavy grappling ways in his last bout, a decision win over Stefan Struve, Tybura is now more than comfortable staying at range, flicking out jabs and kicks and only pressing the wrestling agenda when it’s clear he has an advantage.

The Russian does not throw much and Tybura, despite that surprising head kick knockout of Viktor Pesta almost three years ago, isn’t a one-hitter-quitter threat standing. Both fighters prefer to generate their takedowns off of catching their opponents kicks or working from the clinch. Both fighters have also felt the wrath of fatigue: Against Derrick Lewis, they were in firm control of the contest until they reached a cardiovascular breaking point and then got rushed and knocked out by “The Black Beast.” With both fighters having learned similar stylistic lessons through self-examination and failure, as well as the fact that a win would vault either man a considerable measure forward in the ever-needy heavyweight division, I expect conservative, risk-adverse strategies from them that will lead to a lot of standing, staring, clinching and, eventually, a decision.

An Accumulation Contemplation

Alistair Overeem (-240)
Marcin Tybura (-145)
Ivan Shtyrkov (-165)

Total Odds: (+284)

When it comes to Overeem, we’re looking for some anchors to our parlay, and as mentioned, his -240 number is better than a lot of what is being offered for other strong favorites like Makhachev (-325) or Antonina Shevchenko (-350) over Roxanne Modafferi. Yes, hinging a three-team parlay on an aging Overeem is always going to induce some stress and anxiety given his unsteady past, but the Oleynik matchup is still stylistically preferable. In terms of strong favorites with decent numbers, the only comparable fighter on the card is Michal Oleksiejczuk over Gadzhimurad Antigulov hovering around -220, but with Overeem-Oleynik, we’re dealing with more certain quantities.

I outlined above that Tybura is likely bound for the scorecards against Abdurakhimov, and I do think the bout will be tight and competitive. With that said, I still think the Pole is the righteous favorite. With Abdurakhimov being so shiftless on the feet and Tybura landing at a higher clip and accuracy in the standup, “Tybur” should manage to curry favor with the judges. Also, consider that Tybura completes 61 percent of his takedowns to a paltry 26 percent for the Russian, so if there is a protracted clinch battle, Tybura will likely wind up on top, in addition to the fact that he is a much better positional grappler. In this spot, I’m mighty tempted to replace Tybura with Keita Nakamura against Sultan Aliev at -105, as I think “K-Taro” is the best underdog on the card. However, I’m iffy on his inclusion because of the potential of Aliev holding him down and winning a close, lame decision.

For me, Shtrykov is a must-have in a three-team parlay for this card, where good lines on comfortable favorites are hard to come by. Despite his shiny 15-0-1 record, I don’t think the world of “The Ural Hulk” as a prospect. A lot of that record has been inflated and many of his biggest wins -- like those against Jeff Monson and Antonio Silva -- came under questionable circumstances that put the spotlight on some promotional shadiness from his Titov Promotions backers. With that being said, Shtyrkov is a physical horse now that he’s at 205 pounds, and while I don’t see him as a future title contender, his combination of savage power punching and underrated wrestling should be more than good enough to carry him to victory against Devin Clark, who despite having a quality jab and solid boxing fundamentals, is prone to eating heavy power shots and not recovering. Even if this one goes the full 15 minutes, it will be the Russian landing the damaging blows and generating the kind of round-winning offense to earn him the judges’ scorecards.