UFC 244: Jorge Masvidal vs. Nate Diaz Toe-to-Toe Preview – A complete breakdown

Jorge Masvidal vs. Nate Diaz headlines UFC 244 this November 2, 2019 at the Madison Square Garden in New York City, New York. One…

By: David Castillo | 4 years ago
UFC 244: Jorge Masvidal vs. Nate Diaz Toe-to-Toe Preview – A complete breakdown
Bloody Elbow 2.0 | Anton Tabuena

Jorge Masvidal vs. Nate Diaz headlines UFC 244 this November 2, 2019 at the Madison Square Garden in New York City, New York.

One sentence summary

David: In a world of balls and words, two men will break both of them for our entertainment. Or is that three?

Phil: When cherry-picking stylistic matchups meets corporate cynicism and the result is… ok…?


Record: Jorge Masvidal 34-13 | Nate Diaz 20-11

Odds: Jorge Masvidal -155 | Nate Diaz +145

History / Introduction to the fighters

David: I remember when Masvidal was just an interesting fighter who had big wins at the time over highly-rated lightweights like Yves Edwards, and Joe Lauzon. Only to go to Japan and “lose” to Rodrigo Damm. His early career had always been mired in bad losses sandwiched in between great wins. One night he’s getting reverse triangle choked by Toby Imada. The next night he’s beating KJ Noons. And so it’s been for what has felt like aeons. Masvidal’s sudden rise to “contendership” is definitely driven by savvy marketing. But he’s also an extremely technical fighter who just happens to have a larger than life persona.

Phil: It’d take a heart of stone not to see Jorge Masvidal’s recent run and not be happy to see the long-time action vet and gatekeeper finally get some shine, and I am here to tell you I am that stone-hearted man. OK, yes fine, it’s actually pretty cool. The Askren and Till knockouts kind of ruled, and it’s nice to see Masvidal finally getting some love. But it also feels a bit of a shame that it comes at the expense of the younger fighters who have fought their way up the division. Then again, Masvidal has paid his dues and many of them will have their chance. I guess it just feels like something of a cheat that it took this long to get this kind of organic buzz around a skilled, interesting fighter, and that the whole thing had to be wrapped around this stupid belt. Jorge Masvidal was here the whole time you guys! He was always pretty cool!

David: Like Masvidal, Nate has always been a fighter of stops and starts. Good wins followed up bad losses, rinse, and repeat. Along the way, the usual drama has followed Nate. And a perfect storm developed: a few good wins, and a marketing juggernaut in Conor McGregor turned Nate Diaz from an action gatekeeper to a full blown personality/moneymaker.

Phil: The genesis for the BMF belt rests with Diaz the Younger (as far as I remember anyway). Again I have this general feeling of: Diaz is an undeniably interesting fighter, this is an undeniably interesting fight, but why does the underlying reason for the fight have to be so damn silly? For a person fighting to be the “Baddest Mother Fucker” in the UFC, he fights about once per year, and only does it against tiny strikers nowadays. That being said, Masvidal is about the most dangerous matchup he’s fought of late: someone who can kick and wrestle and who has never fought at featherweight.

What’s at stake?

David: There’s no doubt that the stakes are more artifact-based than anything that could tangibly affect the hierarchy of the division. What makes this fight interesting isn’t that it’s for the belt (well, a real one anyway), but that there’s no lying about what makes gonna happen. They’re gonna go in, do battle, and call it a night.

Phil: There’s so much more buzz around this fight than there is for Colby vs Usman. I honestly think that’s one of the reasons why they ensured that fight was booked by the time this one went down: there was a chance that this would become the belt that everyone would be asking for; that even if the brass officially retired it the winner would be the one that everyone would call out, ignoring the real welterweight belt, which traces its lineage all the way back to the legendary Johny Hendricks. There’s still a chance that happens!

Where do they want it?

David: Despite the reputation as a street fighter, and Tony Montana-shaped brawler; on volume alone, Masvidal is one of the most technical fighters in the sport. He uses a cold, persistent jab to open up different attacks, such as bodykicks, knees, and overhands. He’s even capable of fighting comfortably from the southpaw stance. He doesn’t have mechanical speed, but it’s functional due to his supernatural timing. And he throws with enough velocity to score KO’s with decent regularity, no matter the weight class he’s in. The problem with Masvidal is that no matter how durable, tough, and powerful he is, the technician in him would rather take over than the street fighter. Which is ironic and not ironic since his street fighter days were marked by superb technique. I suspect there’s a Joker-Batman dichotomy going on during his brain’s strategy sessions. He wants to figure out his opponent, and open up mini-brawls. Doing so takes time, and that’s something the streets don’t count: the clock. It’s worth mentioning his grappling since I suspect it’ll be a factor. Even though Nate isn’t a great wrestler, Jorge’s defense is built more around being able to wall walk, and hit the switch than being athletically impenetrable. The latter would be better to have than the former against a fighter like Nate, who’s great at maintaining grip, posture, and positioning.

Phil: Masvidal is someone who could justifiably be accused of cruising through fights in the past. As far as well-rounded fighters who could compete in every phase, Jorge has always been ahead of the game: the kind of consummate technician that we see more frequently nowadays, but who barely existed back when Masvidal was roaming around Shark Fights, Strike Force and Bellator. With this depth of skill came a tendency to accept the fight he was given. If an opponent wanted to grapple, Gamebred was happy to fight them there. If they wanted to strike with him, he’d do that too. Not only did this make him vulnerable to losing to specialists (the Toby Imada triangle being both an incredible MMA moment and something which should have never ever happened to a talent like Jorge), but to losing fights to sudden shocking moments of offense. Many fighters tend to lose their aggression and ability to pull the trigger as they age out, so it’s been particularly welcome to note that Masvidal has been upping his aggression, and to see how impressive the results have been. He’s coming out of the gate throwing without fear, blitzing in rather than sheltering behind his (admittedly superb) jab, and punctuating combinations with kicks. Beyond this he retains all the aforementioned skills: a fine puncher, a savant at catching kicks and countering, and a superb offensive and defensive grappler.

David: Nate was birthed into the world a genetic clone of his brother, but the epigenetic footprint of cage pugilism morphed him into something more unique. Nate has cycled through various incarnations, and never landed on one cleanly. Unlike Masvidal, who struggles within himself, Nate struggles outside of himself. His efficiency is largely dependent in his opponents. Against a striker, his gangly attrition style works gangbusters. Against a wrestler with good grappling fundamentals, his game largely falls apart. So a lot of his best work is the work of opponents assuming that his somewhat crude boxing mechanics won’t translate. They do. And they will. Because no one fights with the Train to Busan method of Nate Diaz, durable and indifferent no matter what schemes his opponent is hatching. He’s still a major threat from his back, but for the most part, he’ll fall back on his Stockton slap, and battle with what is the equivalent of a Tom Cruise stunt; displaying endless cardio and menace.

Phil: Nate Diaz has gone through a few transformations: a come-forward blizzard of punches and clinch fighter broadly similar to his big brother, then a crafty range counterpuncher who worked from the outside and now… back to the first one? At his best Diaz is a surprisingly subtle man, pivoting on the outside to draw opponents into the right hook or southpaw one-two. He’s full of little skills that we don’t necessarily associate with a Diaz: he’s a decent kicker himself, and has always been a fairly diligent and dangerous clinch wrestler (reference his donnybrook with Josh Neer back in the day). I do feel like we might have seen the best of young Nathan, however. Despite any qualms I might have about him cherrypicking his opponents, there’s no doubt that he’s earned his current status with a long, tough career, and it’s still endlessly satisfying to see Dana have to swallow his stupid “needle mover” comments. With that being said, I think he’s grown out of a division where he kind of needed his size. Unlike Masvidal, a fairly quick-footed athlete who is happy in either division, Diaz was a bit of a golem at lightweight and is neither quick nor powerful at welterweight. I also feel like his fabled cardio is starting to erode a bit: he beat up on McGregor and Pettis late, but these felt more like a very tough man gutting out wins while tired than they did an inexhaustible Demetrious Johnson or Colby Covington-esque performance.

Insight from past fights

David: On paper, this fight favors Nate in a very very broad sense: Nate does well overall against strikers. But Nate also gets punished a lot too. It’s like they’re the perfect matchup for him so much as they’re the perfect matchup for him to be underestimated, and gas them out. Masvidal hides his strikes extremely well. Enough so that I could see Nate getting hit with a seemingly random head kick that you would have only not seen coming if you weren’t paying attention to Jorge’s setups. Unlike a lot of the recent strikers Diaz has fought, Masvidal doesn’t fight with an erratic, hurried, or singular pace. He builds, evolves, and counters.

Phil: Nate did not look good in that Pettis fight. He’s always struggled with kickers, but he also seemed to be having issues with reacting to punches. It was only when the fight went deep that Diaz started to show some defensive craft, and by that point Pettis was exhausted.


David: The Rock was at the weigh ins. Will he also be the referee? Because we all know how that ends. Am I the only one who thought Dwayne looked uncomfortable? Perhaps even he knows how corny this belt is.

Phil: Masvidal has always been a fairly proud man who is willing to engage in dick-measuring contests in the cage. What if he’s literally fighting for a “BMF” belt in front of Robert Duran? Does that make him fight more smarter… or more dumber?


David: If this fight happened four years ago, I think Nate takes it, and even then I’d be a little hesitant. But I can’t shake the feeling that Masvidal is gonna be patient enough to eventually get Nate reaching for those grapes. And those grapes will turn to wine. Because that wine is starting to sound like a violin with that cheese and wine. Ho, ho. I’m actively hyped up for this fight. But more for what it represents. The fight itself will be exciting, but I also expect it to be technical. Jorge has what it takes to run away with the action in his favor, but I wonder how much comfortable he’ll remain in the championship rounds. In some ways, I find it a close match (as we get into the last half), and lopsided in others (early exchanges, and any potential grappling scramble). Jorge Masvidal by Decision.

Phil: Diaz has historically been the one of the two who has picked up the more impressive scalps. While he probably lacks the physical talent of Masvidal, he’s just a more natural competitor and mentally tougher. He tries to win harder. With that being said, the direction that these two have trended in can’t really be ignored, and neither can the fact that Diaz also holds the tougher losses in recent memory. For example: Masvidal lost a razor-close decision to Bendo, and Diaz got absolutely mopped. Nate’s main path to victory is to outpace Masvidal and draw him into a brawl, but Masvidal seems increasingly tough to pressure and outpace. Beyond that he seems more defensively aware nowadays, a better wrestler should the fight go there, is a better kicker, and probably has a reasonably pronounced speed edge. Jorge Masvidal by unanimous decision.

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David Castillo
David Castillo

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