(Editor’s note: This story originally published Oct. 29, 2019.)
MMA Junkie analyst Dan Tom breaks down the UFC’s top bouts. Today, we look at the main event for UFC 244.
UFC 244 takes place Saturday at Madison Square Garden in New York. The main card airs on pay-per-view following prelims on ESPN2 and ESPN2/ESPN+/UFC Fight Pass.
Jorge Masvidal (34-13 MMA, 11-6 UFC)

Staple info:
- Height: 5’11” Age: 34 Weight: 170 lbs. Reach: 74″
- Last fight: Knockout win over Ben Askren (July 6, 2019)
- Camp: American Top Team (Florida)
- Stance/striking style: Orthodox/kickboxing
- Risk management: Good
Supplemental info:
+ AFC welterweight title
+ Undefeated in the streets
+ 15 KO victories
+ 2 submission wins
+ 8 first-round finishes
+ KO power
+ Slick boxing technique
^ Accurate shot selection
+ Improved kicking game
+ Solid balance and footwork
+ Active transition and clinch game
^ Strikes well off of the breaks
+ Excellent wrestling ability
+ Underrated submission acumen
+/- 6-2 against UFC-level southpaws
Nate Diaz (20-11 MMA, 15-9 UFC)

Staple info:
- Height: 6’0″ Age: 34 Weight: 170 lbs. Reach: 76″
- Last fight: Decision win over Anthony Pettis(August 17, 2019)
- Camp: Cesar Gracie Fight Team (Stockton, Calif.)
- Stance/striking style: Southpaw/boxing
- Risk management: Fair
Supplemental info:
+ “The Ultimate Fighter 5” winner
+ Brazilian jiu-jitsu black belt
+ 5 KO victories
+ 12 submission victories
+ 8 first-round finishes
+ Consistent pace and pressure
^ High-volume approach
+ Excellent boxing technique
^ Accurate jabs and crosses
+ Deceptively strong clinch fighter
+ Superb submission grappler
^ Solid transitions/comfortable in bad positions
+ Dangerous guard game
^ Excellent leg dexterity
+/- Physically durable/traditionally takes damage
Point of interest: Stockton slap vs. South Florida scrap
The main event for UFC 244 features a fun pairing of two fan favorites who will slug it out for the title of “Baddest Mother F*cker.”
Initially stepping into MMA from the backyard brawling scene, Jorge Masvidal has turned into one of the savvier strikers among his contemporaries, operating with the comfort of a longtime veteran. Feinting forward and initiating with his jab, Masvidal has always had a knack for pulling and returning punches with his opponents.
At lightweight, the Cuban’s style and available output had him arguably too comfortable at times, costing him crucial rounds in close fights – fights that many thought he won. That said, we have seen a different iteration of Masvidal since his ascension up the welterweight division.
Now pursuing much more aggressively, Masvidal will mix in his improved kicks off of Thai-style marches. Working well off of his patented left hand, the 16-year veteran asserts himself down the centerline with authority, varying between straight shots to the head or hooks to the body.
Masvidal, who seldom extends himself too far out of position, can be hard to hit cleanly more often than not. However, his comfort in exchanges has shown to cost him both blitzes and counters at times. And despite Masvidal going 6-2 against UFC-level southpaws, he is not beyond being tagged with long left crosses (as we saw in fights with Darren Till, Michael Chiesa and Tim Means).
Sure, Masvidal was able to eventually make adjustments and win said fights, but that punch, in particular, is the last strike you want to give Nate Diaz – a man who can take the steering wheel in a fistfight at a moment’s notice.
Another fighter who came up in an environment where throwing hands were far from foreign concepts, Diaz demonstrates the ability to box with the best of them when it comes to MMA. Under the tutelage of Richard Perez (who is also the boxing coach of Nick Diaz), we have seen the younger Diaz brother steadily sharpen his skills standing.
Firing jab-cross continuums with the snap of a coiled cobra, Diaz will off-set striking rhythms, disrupting a fighter’s timing and subsequent approach. Coupled with unabashed physical taunts and mental warfare, Stockton’s own can sneakily steal the momentum of a fight right out from his opponent’s feet.
Although Diaz has been relatively inactive in recent years, he showed us in his last fight that his cult status isn’t the only thing that has been growing.
Against Anthony Pettis, Diaz displayed an awareness of the traditional defensive pitfalls associated with his boxing-centric stance, smartly managing distance and switching stances in his approach. Diaz also managed to check kicks a bit more than he typically does, something that proved to be crucial being that he was able to injure Pettis’ foot at the beginning of the second round.
Still, legs kicks or not, it is not unusual to see Diaz take damage in victory or defeat, as his in-your-face style of pressure does not come without its costs. Even though a five-round affair is better suited for Diaz’s slow-burn stylings, he can’t afford to start too slow against Masvidal.
If he does, then don’t be surprised to see Diaz make things ugly with his underrated clinch warfare in order the level out the playing field. But with Masvidal’s noted wrestling ability, clinch fighting can quickly turn into sticky situations.
Next point of interest: Grappling gambles and savvy scrambles
Point of interest: Grappling gambles and savvy scrambles

Considering the grappling games that each fighter keeps in his back pocket, I will be curious to see who initiates first in this department.
For my money, I suspect it will be Masvidal.
Initially known as a striker, Masvidal has spent almost an entire 16-year career training with high-level wrestlers at American Top Team, which, in turn, has forced him to improve his wrestling. Even though Masvidal mainly uses his wrestling for defensive purposes, we’ve seen the 34-year-old incorporate wrestling tactics in his battles with Tim Means and James Krause given the fighting style and physical frames at hand.
That said, Diaz is a deceptive fighter to wrestle with in close quarters and has made many fighters regret trying to tangle with him.
Not only does Diaz have his patented front-choke threats to go to, but he also carries some quiet craftiness inside the clinch that could see the light of day. Emphasizing more on overhooks than underhooks, Diaz will use this tie-up to either set up his patented Uchi Mata hip toss or open up opportunities for sneaky trips and guard pulls.
Diaz also reminded us in his last outing how dangerous and proficient he is in transition, only needing but a moment to shift the fight’s momentum from the front-headlock position, landing vicious knees on Pettis. If Diaz ends up losing position and has to fight from his back, the Cesar Gracie black belt’s leg dexterity offers him plenty of options from guard attacks to leg locks that allow for scrambles and submission opportunities.
Nevertheless, no matter how good Diaz’s jiu-jitsu is, he cannot afford to sleep on the grappling savvy of “Gamebred” Masvidal.
Not only is Masvidal someone who Demian Maia credits as having the best defensive jiu-jitsu he’s ever faced in MMA (due to the difficulty he gave the Brazilian), but the Cuban fighter also expertly navigated past the submission threats of Pettis in a recent grappling match.
Sure, that contest with Pettis was more for fun than anything, but Masvidal – whether he’s in or out of the cage – has shown an ingrained, near-effortless technical savvy in the way in which he flows from defending submissions to countering wrestling positions, smoothly striking off of separations without a second thought.
Unless he’s stunned or seriously compromised, this version of Masvidal will be much harder to submit than the one we saw fall to Toby Imada ten years ago.
Next point of interest: Odds, opinion and prediction
Point of interest: Odds and opinions

The oddsmakers and public seem to be siding with the fighter from South Florida, listing Masvidal -175 and Diaz +155 as of this writing.
Considering that Diaz has been favored to win just two of his last 13 fights (using closing betting lines), then I suppose it’s not a huge surprise to see Diaz come in as the underdog here. That said, Diaz – as per usual – is a live dog.
Diaz is incredibly durable and built for five-round fights, unabashedly turning up the volume anytime he senses opposition faltering. If the iteration of Diaz we saw against Pettis was at all ring-rusted from his layoff, then expect to see a sharper version of Stockton’s finest this Saturday.
Diaz, unlike Masvidal, has kept a visibly-lower media profile ahead of this contest, something that could play into the fight.
Masvidal is no stranger to the game and has generally handled media well throughout his career, but the magnitude of a main event like this is something like no other (especially if you’re doing the heavy lifting). The Cuban veteran, despite being long-hailed by hardcore MMA followers for years, has only recently hit the consciousness of the mainstream – a place where Diaz has had more time to adjust to.
If Masvidal allowed his preparation to be affected by his recent success (a la his favorite fighter Roberto Duran, whose stardom also erupted after besting an undefeated combat sports star), then we could see his game start to unravel in the later rounds via Diaz’s vaunted pressure.
It’s a fight where you hate to see either fighter lose, but I’m ultimately siding with Masvidal. Though Diaz could definitely take over in the mid-to-late rounds, I suspect that Masvidal – who traditionally does well with southpaws standing – does enough damage early with his underrated kicking game and secures close rounds with takedowns to earn himself a unanimous decision in what should be a competitive contest.