Preview: UFC 244 ‘Masvidal vs. Diaz’

Masvidal vs. Diaz

By Tom Feely Oct 30, 2019

The ordering process for Ultimate Fighting Championship pay-per-views has changed: UFC 244 is only available on ESPN+ in the U.S.

Is it safe to talk about this event? Its predecessor at Madison Square Garden had a thrown-together feel, but the 2019 iteration came together early and has mostly stayed intact as one of the best lineups of the year.

The Jorge Masvidal-Nate Diaz main event at UFC 244 on Saturday in New York is a perfect fight at a perfect moment, but beyond that, there is plenty of fun stuff that should answer some important questions. Is a move to middleweight the right change for Darren Till? Can Stephen Thompson answer a violent new welterweight contender? How does Gregor Gillespie fare against his strongest opposition to date? Can one building hold the sexual energy of Derrick Lewis and Johnny Walker?

Now to the UFC 244 “Masvidal vs. Diaz” preview:


#3 WW | Jorge Masvidal (34-13) vs. #7 WW | Nate Diaz (20-11)

ODDS: Masvidal (-165), Diaz (+145)

Perhaps we should nominate Diaz for “Matchmaker of the Year.” When it was announced that Diaz would return from a three-year layoff at UFC 241, there was so much hand-wringing that his comeback would actually take place that there was not much thought about what would be next. As a result, it came as a pleasant surprise when, after Diaz beat Anthony Pettis, he used his platform to call out Masvidal. After all, it was a fight that made perfect sense. Both men became hardcore favorites due to their in-cage machismo and willingness to keep things real, only to become legitimate stars later in their careers.

Diaz’s rise has been well-documented. For years, his older brother was the much more prominent fighter, but the younger Diaz continued to make a name for himself in entertaining but inconsistent fashion. Antics like his flexing in mid-triangle choke against Kurt Pellegrino earned him his own cult fanbase, even if Diaz had trouble getting over the hump to true title contention against stronger wrestlers who could control his skinny frame. Diaz did eventually find a path to then-lightweight champion Benson Henderson, with an extended beatdown of Donald Cerrone serving as a particular breakout win along the way. However, a loss to Henderson and a subsequent defeat against Josh Thomson -- the lone knockout loss of Diaz’s career -- seemed to relegate him back to cult favorite status. Things got a bit weird after that, as they often do with the Diaz brothers. After a rebound win over Gray Maynard, Diaz would fight only twice over the next two years due to his unhappiness with the UFC. The first bout saw Diaz look seemingly unprepared in a one-sided loss to Rafael dos Anjos, but after a yearlong layoff, Diaz managed to lure Michael Johnson into his type of fight and earn a much-needed victory. Afterward, Diaz decided to unleash a profanity-laced callout of Conor McGregor that quickly got cut short on Fox’s airwaves. However, it built enough heat that when McGregor suddenly needed a late-notice opponent, Diaz got the call. As it turns out, Diaz was the perfect foil to make his feud with McGregor one of the best in the sport’s history. The two were more than willing to puff out their chests and talk an immense amount of trash, and even better, McGregor was not a wrestler, opening the door for Diaz to win their first fight and set up a rematch that broke all sorts of box-office records. The rematch narrowly went McGregor’s way, but rather than set up a trilogy, Diaz was content to sit on his laurels -- and piles of cash -- until the right opportunity arrived, which apparently turned out to be Pettis. With another impressive performance from Diaz out of the way, the time has come for the truly fun stuff, particularly since Diaz has now hit the level where he can apparently call his own shots.

It has been just as long of a journey to stardom for Masvidal, who seemingly hit every possible stop before eventually finding his way to the Octagon. Coming out of the same Miami street-fighting scene that birthed Kimbo Slice, Masvidal eventually went legit, and his early mixed martial arts record is full of seemingly every promotion of the era, both with and without staying power. No matter where Masvidal plied his trade, he was more than willing to bring the violence, and come 2011, he eventually found a permanent home in Strikeforce -- right before it was absorbed by the UFC. Masvidal found himself in high-level situations long before his UFC run, but his career was often an exercise in frustration. He had enough skill in every aspect of the sport that he could hang with just about anyone, but his tactical adjustments often came at the expense of his greater success, as he would focus on individual exchanges, only to find himself losing the fight as a whole. That issue is probably best exemplified by a stretch in 2015-16 that saw him drop three out of four fights by split decision, including his infamous loss to Al Iaquinta that made him decide to move to welterweight. Masvidal easily could have won each fight outright, but after moments of success, he was more than willing to take his foot off the gas and essentially coast to a narrow loss. In recent years, that tendency has come and gone. It looked like Masvidal had figured things out after a win over Cerrone put him in title contention and a bout against Demian Maia that was a close loss in all the best ways. However, they were followed by a vintage Masvidal performance in all the worst ways against Stephen Thompson, as “Gamebred” was content to be competitive but never quite take over the fight. Masvidal was out of sight and out of mind for 2018, but upon his 2019 comeback against Darren Till, he surprisingly seemed to fix a lot of his mental issues. In the past, Till would be exactly the type of low-output puncher that could lure Masvidal into a slower pace, but the American Top Team mainstay instead kept up the volume and eventually put away the Brit in a violent finish. Then there is Masvidal’s last bout against Ben Askren, about which not much else can be said. Masvidal immediately shot out with a flying knee, sent Askren’s consciousness into another galaxy and walked away with the quickest finish in UFC history, even with a second or two delay before the stoppage. Suddenly, Masvidal has gone from battle-tested veteran to one of the most exciting stars in the game, and a win here could put him in contention for long-awaited shot at UFC gold.

In a way, the script is flipped on how this fight might play out now versus how it might have gone earlier in their careers. Diaz’s comeback performance against Pettis was much more measured than usual, while Masvidal is the one who has finally started pressing his brand of violence upon his opponents. Frankly, that only seems to play more into Masvidal’s hands. As long as Masvidal can stay mindful of the overall fight, he should be able to handle this match, particularly on the feet. If Diaz is no longer as concerned with drowning his opponent with volume, Masvidal should be able to pick him apart from range and hit the harder individual punches in any close exchanges. Diaz’s submission game -- typically his ace in the hole -- might not be as effective here. Masvidal is one of the more underrated grapplers in the sport, as he showed by surviving on the mat against Maia. There is always some concern that Masvidal will retreat into his old style, but the machismo of a Diaz fight should also help keep him engaged and willing to take over the fight. It should be weird and fun, but Masvidal by decision is the clear pick.

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