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UFC 244 predictions, preview, and analysis

Who is the baddest motherfucker in UFC?

We’re about to find out, courtesy of the UFC 244 pay-per-view (PPV) welterweight main event between Jorge Masvidal and Nate Diaz, which takes place tomorrow night (Sat., Nov. 2, 2019) inside Madison Square Garden in New York City. Sure, the “BMF” belt is a lame-duck marketing tool to sell small-minded rubes a $60 fight card with no legitimate championship showdowns, but blah-blah-blah GANGSTERS, BRO!

In the UFC 244 co-main event, Darren Till will try to prove his weight cut led to shitty performances against Masvidal and Tyron Woodley when he collides with Kelvin Gastelum, another former welterweight who is legitimately talented — as well as legitimately clueless on how to properly cut weight. Elsewhere on the card, Stephen Thompson tries to pull the chute on his 170-pound free fall opposite Vincente Luque, while Derrick Lewis looks to get back into the win column against Bulgarian decisionator, Blagoy Ivanov.

Dumb fact of the day: I thought Blagoy Ivanov and Shamil Abdurakhimov were the same fighter for like three years.

Before we break down the five-fight main card, which airs exclusively on ESPN+ PPV (sign up here), be sure to see what the man with the iron bladder, Patrick Stumberg, had to say about the UFC 244 preliminary cards here and here. In addition, all the “Masvidal vs. Diaz” odds and betting lines can be dissected here.

Let’s get to it.

170 lbs.: Jorge “Gamebred” Masvidal (34-13) vs. Nate Diaz (20-11)

The long-awaited “gangster” fight between Jorge Masvidal and Nate Diaz is finally here and I can tell you without exaggeration it could not have come soon enough. Not because I’m particularly amped by their welterweight match up, I’m just nauseated by how insufferable Masvidal has become in the wake of his flying-knee knockout over Ben Askren. It was a record-breaking finish and he deserves every accolade received, but the “super necessary” media tour has turned him into George Constanza, annoying everyone around him with his constant bragging about that hospital parking spot. In my opinion, his destruction of Darren Till was more impressive because it required more grit to achieve whereas the “Funky” finish was more like one of those trick plays a football team will run on the opening down of the Super Bowl to try to catch everyone with their pants down. That also tells you just how varied “Gamebred” is when it comes to his stoppages and I can’t remember a more savage ending than his obliteration of Donald Cerrone back in 2017. As dumb as this gimmicky main event is, I won’t argue that Masvidal is one bad motherfucker.

So too, is Diaz, who can be equally frustrating in terms of wins and losses. It’s amazing how the Stockton slapper can look so above it all in commanding performances against the aforementioned “Cowboy,” then look completely amateurish in lopsided defeats to the likes of Rafael dos Anjos. I don’t think there are any more surprises in Diaz fights, as fans can bank on world-class jiu-jitsu, Duck Hunt dog-level taunting, and the occasional crimson mask. His record will tell you that wins are easy to come by against opponents who’ve yet to master poise, but seasoned strategists also recognize his lead leg is like chum in the shallow waters of Eastern Cape, South Africa. Like any competent striker, Diaz does his best work when you give him room to breathe, with E. Honda face slaps coming in whack-a-mole style. Knockout power has never been part of his DNA and that long, lanky frame has often betrayed him against the division’s best wrestlers. Every time I watch Diaz fight I’m reminded of that scene in Rocky IV when Drago gets back to his corner, exhausted from throwing so much heat and getting nowhere, and telling trainers that Rocky is like a piece of iron.

Fights can sometimes be tricky to predict but almost always follow the same basic rules of analysis. Strengths vs. weaknesses, past performances, striking against grappling, etc., but these two are all over the map, making it difficult to predict exactly which version is going to appear on fight night. The Anthony Pettis win was the first time Diaz has competed since 2016 and it showed, as the former TUF champ looked clunky and out of breath. I would be shocked if those same issues were present against Masvidal now that Diaz is back in the groove, but I can’t overlook the fact that he’s now 34 and has a lot of miles on those Stockton tires. I guess my biggest question for this fight, is how much actual fighting will take place, since both combatants like to taunt, showboat, and play to the crowd. If they bite down on their mouthpieces I think we can expect Diaz to land more volume while Masvidal does more damage. Where that leaves us after five rounds of action is unclear, but I can tell you I would not want to be a judge in this fight. To be quite honest, I don’t even care about a finish, I just want this showdown to live up to half the amount of hype it’s been getting. Might go a long way in validating that “BMF” belt.

Prediction: Masvidal def. Diaz by split decision

185 lbs.: Kelvin Gastelum (15-4, 1 NC) vs. Darren “The Gorilla” Till (17-2-1)

Remember the old days when fighters would hit a rough patch and drop down in weight? Now everyone is moving up, partly because USADA banned IV rehydration but mostly because dying in the sauna is bad for your career. One thing that hasn’t changed is the painful truth that success and failure are not predicated on weight. Kevin Lee recently went up to welterweight and got smoked, as did Luke Rockhold, whereas Kelvin Gastelum packed on a few extra pounds and found himself at the top half of the middleweight division. No doubt Darren Till will try to replicate that success after saying goodbye to his brutal weight cuts and competing in a division better suited for his wide, muscular frame. In fact, “The Gorilla” will enjoy a three-inch advantage in both height and reach. It probably won’t make a difference after watching Gastelum find success against the long and lean Israel Adesanya, but Till has heavy hands, so it’s certainly worth mentioning.

Watching “The Last Stylebender” have great success before and after his Gastelum fight went a long way in legitimizing The Ultimate Fighter (TUF) 17 champ as a credible threat to anyone competing at 185 pounds. He’s got some of that Henry Cejudo cringe going on outside the cage, but inside he’s a surprisingly effective striker with a solid wrestling base, along with the cardio you would expect from a 28 year-old athlete in his prime. In short, he can do it all and do it quite well, and those fighters who don’t take him seriously end up in the loss column. Michael Bisping and Ronaldo Souza come to mind. That said, this is also just the second time in nearly four years that Gastelum has faced an opponent in his 20’s, a span of eight fights. The other was Adesanya, who turned 30 back in July. I reckon he’ll have the same speed advantage against Till that he had against some of those elder statesmen, the price the Liverpool power-puncher has to pay for being a middleweight unit.

I would say that most of the tricks that Till got away with at welterweight due to his size and power won’t work at 185 pounds, but he’s facing a fellow welterweight import, so the only thing that has changed is the number on the scale. I would expect it to make “The Gorilla” fresher and in many ways, more dangerous. I would also expect it to make him slower and more flat-footed as the rounds crawl by. Not just because of the additional muscle, but also because fighters who no longer need to cut a tremendous amount of weight don’t ratchet up the cardio like they do when their purse depends on it. Gastelum has already settled into his new home and if we’re being honest here, we can’t overlook the fact that he’s also fought one current champion and four ex-champions in his last five fights. Till faced some killers of his own, but Donald Cerrone is a natural lightweight and the Stephen Thompson fight was five rounds of pat-a-cake (we don’t even want to talk about what happened against Jorge Masvidal and Tyron Woodley). With Gastelum’s speed and aggressiveness, I don’t see how Till get the breathing room he needs to settle in and find his range, so unless Gastelum does something stupid — like charge forward with his hands down and chin up — I think Till gets knocked around for three rounds in a fight that is sure to please the New York faithful.

Prediction: Gastelum def. Till by unanimous decision

170 lbs.: Stephen “Wonderboy” Thompson (14-4-1) vs. Vicente “Silent Assassin” Luque (17-6-1)

It’s been a weird turn of events for Stephen Thompson, a flashy and talented striker who at one point, looked like the most dangerous fighter at 170 pounds. He laid waste to Robert Whittaker back when “The Reaper” was making waves at welterweight, then blew the doors off Johny Hendricks back when that sort of thing still meant something. “Wonderboy” also registered victories over Rory MacDonald and Jorge Masvidal and the argument exists he won at least one of his Tyron Woodley title fights. So what the heck happened? Well, that’s hard to say, but the former kickboxing phenom turns 37 in three months and Father Time can be unnecessarily cruel to athletes who rely on speed and precision for their success. If we flip the coin, we can say his Darren Till loss was a wash because no one stayed awake long enough to see it end and maybe he just got caught in his knockout loss to Anthony Pettis. This fight will (hopefully) answer that question.

Vicente Luque has quietly taken over the welterweight division over the last four years, racking up an exceptional 10-1 record since his TUF 21 Finale back in late 2015. In addition, the Brazilian is the winner of six straight with five violent finishes and had the fans on their feet in his bloody war of attrition opposite Mike Perry. What’s kept him out of the Top 10 is his level of opposition. Perry remains unranked, as does every other fighter who fell to “The Silent Assassin.” The one exception is No. 4-ranked Leon Edwards, but based on what “Rocky” has been able to do at 170 pounds — win eight straight and 10 of his last 12 — Luque’s 2017 decision loss feels more forgivable. The quasi-analyst in me wants to be critical of his run-and-gun offense, which makes for some exciting battles but shortens careers, yet how do you knock a guy who continues to win, earn post-fight bonuses, and electrify the fans? If anyone can use that sort of opponent after stinkers against Woodley and Till, it’s Thompson.

I’m not feeling very optimistic, at least in terms of getting another “Fight of the Night.” No doubt Luque will bring hellfire and brimstone tomorrow night in “The Empire State” and those long, lean legs of Thompson are certainly on the menu. I just have a hard time imagining a striker with the pedigree of “Wonderboy” — unless he’s completely shot — getting lured into the kind of phone booth fight that made Bryan Barberena and the aforementioned Perry richer in pocket but poorer in spirit. Thompson is a master of the rat-tat-tat-then-circle-back offense, an effective way to frustrate an opponent while reducing them to lumbering brawlers. The Luque camp knows this and will undoubtedly prepare for that very scenario, but gameplays have a way of going out the window once pride (and facial lacerations) take over. Plan for a very busy first round full of oohs and ahhs while Luque gets his licks in, followed by a slower, more methodical striking clinic in rounds two and three.

Prediction: Thompson def. Luque by unanimous decision

265 lbs.: Derrick “Black Beast” Lewis (21-7, 1 NC) vs. Blagoy “Baga” Ivanov (18-2, 1 NC)

What separates MMA from any other sport, if you even want to call MMA a sport, is that you don’t even have to be that good to make it to “the show.” Brock Lesnar is big, powerful, and agile, a freak athlete, and yet he was not good enough to make the starting line up after hooking up with the Minnesota Vikings. In UFC, he only needed three fights to win the heavyweight title. That’s not unlike the ascension of power-punching fan favorite, Derrick Lewis. The “Black Beast” is certainly entertaining, both inside and outside the Octagon, but his technical prowess leaves a lot to be desired. I would say Lewis has the same gameplan for every fight, but that would require him to have an actual gameplan to begin with. Sorry, but swinging for the fences and hoping you don’t get knocked out in the process does not constitute strategy. That’s why Daniel Cormier and Junior dos Santos, two former champions with polished skill sets, made the hulking Texan look like some beer-swilling shmuck they pulled from the stands. I know this reads like harsh criticism for a guy who scored 18 knockouts in 21 wins, thanks to the kind of punching power that could knock the door off a bank vault, so I will give him credit for his fight frequency. Lewis and his notoriously bad back competed 17 times in the span of five years, an astonishing statistic for the heavyweight division.

Facing the surgically-repaired “Black Beast” is the nearly-indestructible Blagoy Ivanov, who came over from World Series of Fighting (WSOF) Professional Fighters League (PFL) with a tremendous amount of hype. Maybe he’s trying to build some suspense or just hasn’t figured out how to get out of first gear, because “Baga” had 12 finishes before hooking up with Dana White and Co. and now has zero. Granted, it’s only been three trips to the cage, good enough for a 2-1 record, but this is the same fighter who upset Fedor Emelianenko at the 2008 World Sambo Championships and survived a knife to the heart in 2012. If you want to talk about gangsters and “BMF” titles then we should talk about Ivanov. His grappling was and remains his greatest attribute and he’s been honing his craft with the top-shelf wrestlers at American Kickboxing Academy (AKA), though for this fight he trained exclusively at the promotion’s Performance Center in Las Vegas. To be honest, there hasn’t been anything memorable about his first three fights for UFC and I don’t expect this showdown to break that streak. Ivanov just doesn’t have an exciting style and he’s facing a reckless bulldozer with death in his hands.

There are a couple of concerns for Ivanov heading into the “Big Apple,” starting with his height. The 5’11” Bulgarian gives up four inches in that department and has a six-inch reach disadvantage. I suppose it doesn’t matter, as no one expects him to work the jab or strike from range. That said, the threat of the knockout remains for all 15 minutes, a lesson Alexander Volkov learned the hard way at UFC 229. Ivanov also has to be careful not to burn out his tank trying to make this WrestleMania. I know that it’s only a three rounder, but Lewis is more than just big and heavy, he’s thick in his legs and his weight distribution makes him difficult to topple or control for anyone not named Cormier, one of the best to ever do it. Expect some of the usual tricks from Lewis: a random spinning kick, a sloppy bum rush, some makeshift wrestling, and lots and lots of sweat. Barring an act of wanton stupidity, Ivanov should be able to weather the initial blitzkrieg and settle in for a long night of grappling and control. It may not be pretty, but winning ugly is still winning.

Prediction: Ivanov def. Lewis by unanimous decision

155 lbs.: Kevin “Motown Phenom” Lee (17-5) vs. Gregor “The Gift” Gillespie (13-0)

Kevin Lee has spent the last three months talking about his move to Tristar gym and how training with former welterweight champion, Georges St-Pierre, has transformed him into a more compete fighter after some struggles in his last showing. That should probably sound familiar to most fight fans, as it’s exactly what the “Motown Phenom” said about his cut to 155 pounds, before jumping up to welterweight and getting submitted by Rafael dos Anjos, himself a former lightweight who did not hold any sort of size or strength advantage. That was all it took to send Lee running back down to his previous weight class where the competition hasn’t gotten any easier. You would think a fighter with Lee’s experience who is still just 27 years old would be improving with age but he appears to be going in reverse, evidenced by listless performances against Al Iaquinta and the aforementioned Brazilian. I can say with some degree of confidence that matchmakers did him no favors here.

Gregor Gillespie is ranked No. 11 at 155 pounds, just one spot behind Lee, which is indicative of his level of competition thus far in UFC. In six trips to the cage, “The Gift” has yet to face an opponent ranked in the Top 15, whereas Lee was saddled with four straight combatants ranked in the Top 10, including an ex-champion and two former title contenders. Having said that, we also need to recognize that Gillespie has done what all great fighters are expected to do: treat the lower end of the division like a Kleenex at a snot party. The 32 year-old New Yorker has racked up five straight finishes and has only seen the third round once in his UFC career. You could probably argue for an even higher-ranked opponent coming off his destruction of Yancy Medeiros, someone like Dan Hooker, perhaps, but Lee will prove to be a formidable test, death-defying weight cut notwithstanding.

Lee was an accomplished collegiate wrestler and used that foundation to build his combat sports career. He’ll lose that advantage in tomorrow night’s fight because Gillespie is a four-time Division-1 All American and 2007 National Champion. It’s one thing to rag doll strikers like Edson Barboza and Magomed Mustafaev, but Lee will get stuffed like a Thanksgiving turkey if he tries to make this a wrestling match against “The Gift.” In addition, the “Motown Phenom” has registered just two knockouts in 17 wins, one of which came by way of doctor’s stoppage. If he can’t score the takedown and implement his ground game, and he doesn’t have a competent striking attack to fall back on, where does that leave him? The loss column.

Prediction: Gillespie def. Lee by submission

That’s a wrap. will deliver LIVE round-by-round, blow-by-blow coverage of the entire UFC 244 fight card on fight night (click here), starting with the ESPN+/ESPN2 “Prelims” matches online, which are scheduled to begin at 6:30 p.m. ET, then the remaining undercard balance on ESPN2 at 8 p.m. ET, before the PPV main card start time at 10 p.m. ET on ESPN+.

For much more on tomorrow night’s UFC 244 fight card click here.

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