UFC 244: Masvidal vs. Diaz - Predictions and Picks

Jorge Masvidal faces Nate Diaz in the much-anticipated main event of UFC 244
Jorge Masvidal faces Nate Diaz in the much-anticipated main event of UFC 244

This weekend sees the UFC return to New York City with UFC 244, and in the main event – assuming it goes ahead, more on that later – we should see a new UFC champion crowned, of sorts at least. Main eventing this show are Welterweights Nate Diaz and Jorge Masvidal, and the bad boys will face off with a brand new title on the line – the UFC’s ‘BMF’ title, and you don’t need me to explain that acronym.

Overall the card is a genuinely great one, too, with recent main event fighters like Kelvin Gastelum, Darren Till, Stephen Thompson, Derrick Lewis and Kevin Lee all competing. In fact, it’s probably the best UFC show this year since August’s UFC 241.

Here are the predicted outcomes for UFC 244: Masvidal vs. Diaz.


#1 Jorge Masvidal vs. Nate Diaz

Can Jorge Masvidal uncork another wild KO like this one when he faces Nate Diaz?
Can Jorge Masvidal uncork another wild KO like this one when he faces Nate Diaz?

Okay, so this preview comes with a caveat; I’m assuming the issues surrounding a supposed positive PED test for Nate Diaz will vanish this week at some point. Diaz is renowned for being a clean fighter (outside of his open use of marijuana, hardly a performance enhancer) and the likelihood of him actually having a “prohibited selective androgen receptor” in his system seems pretty low. As of writing, it appears that USADA have yet to suspend Diaz, so I’m hoping the fight will be on.

Ignoring the current controversy then, this is a tremendous fight between two of the baddest men in the sport when it comes to their attitudes and demeanours. Both men back down from absolutely nobody, and while there isn’t a natural rivalry here like there was between Masvidal and Ben Askren or Diaz and Conor McGregor – in fact, they seem to have a healthy respect for one another – you can bet your life they’ll go nose-to-nose when it comes to weigh-in time.

Jorge Masvidal is a curious fighter in general. ‘Gamebred’ started life as a legitimate street fighter, even starring in similar viral videos as the late Kimbo Slice, and then started fighting professionally back in 2003. It took him the best part of a decade to make it to the top of the sport in StrikeForce, and even when he came into the UFC in 2013, it never really felt like he’d break into the elite level.

Why was this? A couple of reasons, really. Firstly, Masvidal’s build makes him a fighter who doesn’t necessarily fit perfectly into either the Lightweight or Welterweight divisions. At Lightweight he was cutting a tremendous amount which often left him depleted, and while he’s been successful at 170lbs recently, he’s also had some trouble there, quite often due to his lack of size.

The other issue Masvidal has historically had has come from his inconsistent nature. ‘Gamebred’ doesn’t really have a weakness in his game in terms of his skills – he’s best as a boxer but he’s got a highly underrated ground game and is a decent wrestler too – but he’s been known to basically take rounds off, which resulted in his losses to the likes of Al Iaquinta and Benson Henderson, and he’s also far too willing at times to meet his opponents in their own wheelhouse – as he did against Stephen Thompson and Demian Maia.

Most recently though, he’s been running through his opponents in violent fashion. Darren Till knocked him down early on, only for Masvidal to work out his range and knock the British fighter out with a violent combination, and against Askren, he read the game perfectly and timed a flying knee to knock out the wrestler as he dived for a takedown in the opening seconds of the fight.

As for Diaz, everyone knows all about his game at this point, hardly a surprise given the Stockton bad boy has now been in the UFC since 2007 and has had 24 fights in the promotion. Essentially, he’s a double-edged sword for opponents; his boxing is second to none in the Welterweight division and he’s one of the most dangerous grapplers in the division when it comes to submissions too, but outside of that, he can be beaten by fighters who aren’t willing to play his game.

That usually means either wrestling him, using takedowns and heavy top control to hold him on his back and beat him up using ground-and-pound, or using a range kickboxing game based around low kicks to pick him apart from the outside. That’s obviously risky due to Diaz’s long 76” reach, but the likes of Josh Thomson, Rafael Dos Anjos and to a lesser extent Conor McGregor pulled it off.

Essentially, if you’re willing to play Diaz’s game – or he can force you to, as he did with Anthony Pettis in August – then you’re likely to lose. If you’re willing to fight smart and have the skills to do so, he’s extremely beatable. Hence this fight; Diaz basically has the profile and the drawing ability to pick his own opponents, so it’s telling that he’d choose someone like Masvidal rather than angle for a fight with Kamaru Usman or Colby Covington.

It’s a bit of a tricky fight to pick because of Masvidal’s own excellent boxing skills, but he’s also at a reach disadvantage (2”), he’s got the kind of personality to engage Diaz in his own wheelhouse – as I mentioned earlier, a regular mistake ‘Gamebred’ makes – and I’d also suggest Diaz has an advantage in terms of cardio, too.

If Masvidal approaches this calmly and chooses to kick at Diaz’s leg and mix in some takedowns, I feel like he could win, but I can’t see that happening and instead I figure we’ll get a Diaz fight – a brawl with Diaz sneakily using the cleaner boxing technique to wear ‘Gamebred’ down over five rounds. A late stoppage is possible but Masvidal is super-tough so I’ll go with Diaz by decision.

The Pick: Diaz via unanimous decision

#2 Darren Till vs. Kelvin Gastelum

Will Darren Till's move to 185lbs benefit him?
Will Darren Till's move to 185lbs benefit him?

Considering Darren Till – probably the UK’s most popular fighter these days with the loss of Dan Hardy and Michael Bisping – was proclaiming 2019 as ‘The year of the Gorilla’, it’s hardly been plain sailing for the Liverpool native. Till came up short in his attempt to dethrone Tyron Woodley for the UFC Welterweight title last year, but was hoping to rebound when he fought Jorge Masvidal in London in March – only to be violently knocked out in the second round.

That knockout was evidently enough to inspire him to finally make the move to 185lbs, after struggling to hit 170lbs for some time now – missing weight on two occasions in the UFC alone. If Till was expecting to have an easy assignment for his first fight in a new weight class though, well, he was painfully mistaken.

2019 hasn’t been plain sailing for Gastelum either, but it hasn’t all been bad. Sure, he missed out on a UFC Middleweight title shot back in February when Robert Whittaker was sidelined with injury, and he then lost to Israel Adesanya in his attempt to win the Interim title, but that was also the best fight of 2019 thus far and Gastelum also put Adesanya under more pressure than anyone else has been able to do thus far, actually knocking him down and hurting him on a couple of occasions.

For me this largely comes down to how well Till’s body adjusts to 185lbs. He’s certainly got the frame to be a formidable Middleweight – he’s 6’0” and has a long, 74.5” reach – and while we haven’t really seen him face a powerful wrestler yet outside of Woodley, who knocked him down rather than taking him down, his takedown defense has looked solid thus far and he’s also a tremendous pressure-striker.

Till isn’t really a similar fighter to Adesanya; the Last Stylebender has an even longer reach and prefers to attack from range, but there are some parallels when it comes to this fight with Gastelum I think. In that Adesanya fight, Kelvin Gastelum had success when he was able to get inside the taller man’s reach and land quick combinations, and he’ll need to do the same in order to get at Till I think.

Till’s style is based almost purely around pressure. His best performances have seen him use his footwork to corral his opponent against the fence where he tends to hit them with powerful combinations usually ending with his nasty left hand. He’s also adept at clinch striking, particularly with his elbows.

In his win against Stephen Thompson he also showed some skills in going head-to-head with an expert point-fighter and doing well, even if a lot of fans felt ‘Wonderboy’ deserved the decision. Against Gastelum then, it feels like his key to victory is pretty simple – he needs to avoid Gastelum’s takedown, walk him down and trap him against the fence before hitting him with heavy leather.

The problem with that? Gastelum is surprisingly quick at 185lbs and hits remarkably hard, and as we’ve seen in his last couple of fights, Till’s chin perhaps isn’t the sturdiest. Gastelum’s meanwhile appeared to be made of granite or titanium or something equally solid when you consider the punishment he survived against Adesanya.

Can Till win this fight? If he can trap Gastelum against the fence and really hurt him then perhaps, but I just don’t see him being able to do that for three straight rounds without eating something nasty from the TUF 17 winner. Till should have a bright future at 185lbs, but I don’t think this will be a good start for him.

The Pick: Gastelum via second round knockout

#3 Stephen Thompson vs. Vicente Luque

Can Stephen Thompson pick apart Vicente Luque?
Can Stephen Thompson pick apart Vicente Luque?

Prior to 2019 it was largely rare for the UFC to match a fighter coming off a loss with a fighter coming off a win, particularly if the latter was on a long winning streak. That’s not the case anymore, and this fight is the perfect example of that. Thompson was last seen in a violent KO loss to Anthony Pettis, while Luque is riding a six-fight win streak and is 10-2 in the UFC overall.

That doesn’t really matter, though. Basically, this is the big step up that Luque needs to see if he can really lock horns with the elite at 170lbs. For me, it’s a scarily tricky fight for the Brazilian. The shine that was once on ‘Wonderboy’ is now gone thanks to his losses to Tyron Woodley, Darren Till and Pettis, but he’s still a pinpoint accurate striker who easily picked apart Jorge Masvidal when they fought and has given problems to everyone he’s faced.

I’m giving Luque a chance here though for a number of reasons. Firstly, while Thompson has proven tricky to take down during his UFC career, Woodley showed that if you can get him down, he doesn’t exactly have a lot from his back. Luque obviously isn’t close to being as good a wrestler as Woodley, but he’s certainly excellent from the top, particularly with his chokes.

Secondly, Thompson has plenty of knockouts on his ledger, but they’ve tended to come against plodding strikers like Johny Hendricks and Jake Ellenberger, men who didn’t really understand the threat that ‘Wonderboy’ posed. He’s not necessarily a concussive striker, which means someone with the power of Luque will always be in the fight to an extent.

And not only does Luque have power, he’s also one of the most ruthless finishers in MMA today; of his 10 UFC wins, just one has gone the distance – and that fight with Mike Perry could’ve ended on numerous occasion had Perry been less tough. If he puts Thompson down as Till or Woodley did, then this fight is most likely going to be closed out very quickly.

That’s a big if, though, and personally – unless Thompson has really lost a step following that Pettis KO – I can’t see it. Luque is definitely a great striker but he’s also not the fastest fighter in the 170lbs division and I just don’t think he has the striking nuances to land cleanly on a guy like Thompson. Of the other fighters that did, Woodley is scarily quick, Till was surprisingly adept at a point-fighting style and Pettis is Pettis – one of the most unpredictable and explosive men in the sport.

Luque meanwhile is much closer to someone like Masvidal, Patrick Cote or even Robert Whittaker; much more straightforward in his attacks, even in his takedowns, and I think that plays into Thompson’s hands here. This one may garner boos as Luque’s usual aggressive style is tamed, but at the end of the day I see ‘Wonderboy’ with his hand raised.

The Pick: Thompson via unanimous decision

#4 Derrick Lewis vs. Blagoy Ivanov

Derrick Lewis hits as hard as any other fighter in the UFC
Derrick Lewis hits as hard as any other fighter in the UFC

You could say this for most Heavyweight fights, but this one is likely to go one of two ways: either one of these two behemoths will land a huge shot and finish the fight off early, or they’ll both gas and we’ll be presented with a sloppy brawl that’ll be fun to watch, or a horribly slow-paced slopfest that everyone can’t wait for the ending of.

Thus far, Ivanov’s fights have fallen largely into the latter category. He was largely picked apart by Junior Dos Santos in his UFC debut although he had his moments when he was able to draw ‘JDS’ into a brawl, and while he’s since beaten Ben Rothwell and Tai Tuivasa, both fights were slow-paced with Ivanov just about doing enough to win.

Lewis, on the other hand, has had a wild mix of basically everything in his time in the UFC. He’s an odd fighter in that he looks absolutely terrible at times, and yet he has such incredible power in his punches that he’s literally only ever one moment away from finding a knockout shot.

Take his fight with Alexander Volkov, for instance; Lewis was being destroyed for basically 15 minutes straight until he uncorked a ludicrous right hand and finished the Russian soon after. That wasn’t even an outlier, either; he was losing badly to Travis Browne and Shamil Abdurakhimov too before somehow finding the big shot to pull off the win.

Ivanov definitely has ways to win this fight; Lewis is not a good fighter from his back at all and the Bulgarian can definitely wrestle even if he hasn’t really shown it in his UFC career thus far. He’s also powerful enough to hurt Lewis standing, and can probably out-do him in the clinch, too. Having said that, Lewis has made a career of beating guys like this in strange ways, and even though he hasn’t been winning recently, it’s still tricky to pick against him.

I’m going to go with a typical Lewis fight here then. Ivanov will probably have a lot of success early, appear to be beating Lewis up with body shots in particular and maybe even get a couple of takedowns, but in the end ‘The Black Beast’ will land a huge shot and seal the deal soon after. Who knows what kind of fun we could be in for during the post-fight interview? It’s been a while, after all!

The Pick: Lewis via third round knockout

#5 Corey Anderson vs. Johnny Walker

Johnny Walker has rocketed to fame thanks to his explosive style
Johnny Walker has rocketed to fame thanks to his explosive style

Dominick Reyes might appear to be next in line for Jon Jones, but if you ask most fans who the fighter they want to see face the champion next is, Johnny Walker might be the first name that comes to mind. Sure, the curiously named Brazilian has only had three fights in the Octagon – and he’s also coming back from a self-inflicted dislocated shoulder – but wow, those three fights.

Walker stopped Khalil Rountree with a series of standing elbows in his debut, switched off Justin Ledet with a spinning backfist in his second fight, and most recently took out Misha Cirkunov with a flying knee in March. That sounds practically too good to be true, but such is the insane athletic ability of Walker.

The strangest thing is that Walker isn’t a fighter who’s looked perfect on the regional scene prior to arriving in the UFC. He’s always been a crazy athlete, but he’s also lost to the likes of Klidson Abreu and Wagner Prado in his pre-UFC days, and was taken to a decision in his appearance on Dana White’s Contender Series by UFC washout Henrique Da Silva.

The most likely explanation? At 27 he’s just hitting his prime, he’s totally comfortable with his lanky 6’5” frame now, and he’s coming in with more confidence than ever. And so it’s up to Anderson – a much more meat-and-potatoes fighter – to knock him off that pedestal, if he can.

Anderson, the winner of the 21st season of TUF at 205lbs, has slowly matured as a fighter too. Always a powerful wrestler, he used his takedowns and top control to beat the likes of Fabio Maldonado and Jan Blachowicz in his early days, but his penchant for brawling caught up with him in his KO losses to Gian Villante and Ovince St. Preux.

Recently though, he’s looked smoother on his feet and was even able to outstrike Glover Teixeira last year by largely using the threat of the takedown to set up his punches. Can he beat Walker, then? If he can ground him and keep him there, sure. But it’s also a risky bet given he’s been stopped by strikes three times before, and will also be at a reach disadvantage, something he’s not used to given he’s got a 79” reach.

I’d be a major spoiler for everyone if Anderson were able to grind out a win over the explosive Brazilian here but I’m not going to pick it; ‘Overtime’ has been snacking on slower, less athletic fighters recently, and the last time he faced someone as fast and more importantly, as long as Walker, he was knocked out violently by Jimi Manuwa.

With that in mind, I’m going for Walker to uncork another wild knockout here – hopefully setting up a future meeting with Jon Jones in the process.

The Pick: Walker via first round KO

#6 The Prelims: ESPN2 card

Can Gregor Gillespie pick up the biggest win of his career over Kevin Lee?
Can Gregor Gillespie pick up the biggest win of his career over Kevin Lee?

We’ve got four fights on the ESPN2 prelim portion of this show, and wow, the top fight is quite something. Unbeaten Gregor Gillespie takes on former title challenger Kevin Lee in the latter’s return to Lightweight. For me this comes down to whether Lee can stop the takedown. ‘The Motown Phenom’ is a far superior striker, but Gillespie is a former NCAA Division I national champion and is one of the best wrestlers in MMA. He’s also relentless at hunting for the takedown, something that can sap an opponent’s cardio. Given Lee’s cardio issues – at 170lbs as well as 155lbs – I’m leaning towards ‘The Gift’ here. He may face adversity early but eventually I think he’ll force Lee to succumb to his pace and take a decision in somewhat of a upset.

At Featherweight, we’ve got another tremendous fight between Shane Burgos and Makwan Amirkhani. For me this should be Burgos’ fight to lose assuming he can avoid the early rush from ‘Mr Finland’. ‘The Hurricane’ is a huge 145lber with a long, powerful frame and he’ll likely dwarf Amirkhani in the cage. Throw in his remarkably smooth striking skills, and I think he’s got enough to land big shots on the Finn to wear him down for a decision.

Veteran Brad Tavares returns at Middleweight to face off with Edmen Shahbazyan in what should be an interesting test for the newcomer. Tavares is strong in all areas but isn’t a great finisher and also hasn’t fought in over a year. Shahbazyan meanwhile has shown that he can grapple as well as strike, but he certainly hasn’t fought anyone on Tavares’ level just yet. For me this could be a wake-up call for the youngster, so I’m taking Tavares by decision, but a finish from Shahbazyan wouldn’t surprise me.

Finally Andrei Arlovski faces Jairzinho Rozenstruik in a fight that likely won’t be fun to watch. Arlovski won his last fight, picking apart a plodding Ben Rothwell, but Rozenstruik is younger, hits much harder and is also surprisingly quick for a big man. I think he turns Arlovski’s lights out early here – perhaps for the last time in the UFC.

#7 The Prelims: UFC Fight Pass card

Jennifer Maia could capture a title shot with a win this weekend
Jennifer Maia could capture a title shot with a win this weekend

UFC Fight Pass has three fights this weekend too, and headlining that part of the card is a Flyweight battle between Jennifer Maia and Katlyn Chookagian. A title shot for the winner isn’t out of the realm of possibility but this one could turn out to be a bit of a point-fighting contest. I’m going with Maia – I feel like she’s slightly better in all areas – but I could be wrong.

At Welterweight, veteran Lyman Good faces Chance Recountre. Quite how much Good has left in the tank I’m not sure, but he’s a powerful striker and a great athlete and I like him to win this one in his home state. I’ll take Good via KO.

Finally, in an intriguing Featherweight bout, Julio Arce faces explosive striker Hakeem Dawodu. Arce is an interesting prospect; a strong boxer and grappler, he’s also extremely tough, as we saw in his wild fight with Sheymon Moraes last year. Dawodu meanwhile hits incredibly hard and is shockingly fast, even for a Featherweight. I feel like he can win this if he can catch Arce, but it won’t be easy – his loss to Danny Henry showed he’s not an unstoppable force. I’m taking Dawodu via KO, but to see Arce pull this out wouldn’t be a shocker.

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Edited by Alan John