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Expert picks and analysis for this weekend's UFC 244: Masvidal vs. Diaz

Saturday November 2nd 2019 at Madison Square Garden, New York, New York

Main Card: 10 p.m. ET on PPV

Preliminary Card: 8 p.m. ET on ESPN2

Early Prelim Card: 6:15 p.m. ET on ESPN2/ESPN+/UFC Fight Pass

Last week UFC Singapore gave us some entertainment, but largely just impressive showings from some relatively unknown fighters. Loma Lookboonmee had a strong debut as the first fighter to represent Thailand in the UFC. Sergey Pavlovich moved to 14-1 following his second successive first round finish in the UFC. Movsar Evloev overcame the tough challenge of Enrique Barzola to improve his undefeated record to 12-0-0. And Ciryl Gane put the UFC heavyweight division on notice after he schooled Don’Tale Mayes for 14.5 minutes before locking-up a late heel hook submission victory. The better known guys who put on a performance were Beneil Dariush, who made short work of Frank Camacho, submitting him in just over two minutes. As well as Demian Maia who came out on top in his back-and-forth grappler vs grappler main event bout against Ben Askren. Both Dariush and Maia winning meant we went 2-0 with our picks, grabbing us a healthy profit of 4.08 units on the event.

We now look onwards to this weekend’s card, live from Madison Square Garden: UFC 244. It’s a PPV event stacked with not only fun fights, but also relatively close fights. As things stand, no-one is greater than a -250 favorite (best price), meaning that no fight on the card is even close to being a forgone conclusion. I would spend some time running down the most notable fights to watch out for, but quite frankly almost all of them should be worthy of your attention. Of course it’s impossible not to mention that Johnny Walker will be fighting, but realistically this card as a whole is up there with UFC 235 in the way of expectations. Anyway, despite the USADA hoopla last week, it’s here and we’re getting it… Let’s jump into this week’s UFC picks for UFC 244: Masvidal vs. Diaz!

Two Leg Parlay:

Katlyn Chookagian vs. Jennifer Maia

Early Prelim Card: Featured Women’s Flyweight Bout – 125lbs

Katlyn “Blonde Fighter” Chookagian – Record: 12-2-0 / #1 Ranked WFLW

Jennifer Maia – Record: 17-5-1 / #5 Ranked WFLW

You know how I just said almost all these fights should be worth out attention? Well this is arguably the only exception. This fight would be a great surprise if it’s anything but a typical Katlyn Chookagian fight. She’ll stick and move, using her extremely evasive style to throw lengthy jabs to the air in front of Maia’s face, and kicks to Maia’s midsection. Just pitter-pattering away at her over the fifteen minutes as Maia plods forward looking to hit Chookagian with one of her significantly more powerful strikes. This may not come across as if I’m heaping praise onto Chookagian, but she’s actually one of my favorite fighters to bet on.

Her style isn’t the most fun to watch, but it’s proven to be immensely effective. Even though a good portion of strikes don’t land, or at least not with any real pop, she does have outstanding output and it’s proved very friendly for the judges to score. Take Katlyn here as the first leg of the parlay. Maia’s not to be overlooked, but she doesn’t have the speed, volume, nor grappling to present Chookagian with any real issues.

First Leg of Parlay: Katlyn Chookagian @ -162

Kevin Lee vs. Gregor Gillespie

Main Card: Lightweight Bout – 155lbs

Kevin “The Motown Phenom” – Record: 17-5-0 / #10 Ranked LW

Gregor “The Gift” Gillespie – Record: 13-0-0 / #11 Ranked LW

This is an odd fight for the UFC to make. Kevin Lee just unsuccessfully stepped-up to welterweight to take on Rafael Dos Anjos in a main event earlier this year. He’s now ridding a two fight losing streak and he’s 1-3 in his last four fights. It’s always a bit of a red flag when someone steps up in weight, only to then go straight back down again following a loss. Lee’s always been a big lightweight, and it shows when we see him looking drained at weigh-ins. He’s perhaps not a super marketable guy, but you’d have to imagine that the UFC wouldn’t want to simply throw one of their youngest lightweight prospects to the wolves yet again. However, for whatever reason, they’ve decided to do just that.

Lee will now be taking on an absolute nightmare opponent in Gillespie. Gregor only lives for two things, to wrestle and to fish. His wrestling is so elite, he’d have competed and likely won gold medals in the Olympics by now if he didn’t have to contended with the Jordan Burroughs in his weight class. He’s undefeated and shows no current sign of slowing down as he heads into his fourteenth pro fight.

Kevin Lee will undoubtedly have the edge in the striking, but in a Gillespie fight, that only takes people so far. His striking is ever improving, and when he shoots a takedown or locks up with his opponent, it’s only a matter of time before the fight hits the deck. Lee’s got some decent wrestling under his own belt, but it still has nothing on what Gillespie has faced in the past.

It’ll be interesting to see what changes Lee has made to his game now that he trains at TriStar (where GSP trains), but in all likelihood it shouldn’t change that this fight will be heading into Gillespie’s world early on.

I see them trading for a minute on the feet, but it won’t be long until Gillespie takes him down and ragdolls him for the duration of the first. From there Lee will likely fatigue as he generally has shown to do after being outworked in the grappling. From there Gillespie’s game plan will just get more intense and have more success as Lee wilts under his pressure, either resulting in a late stoppage, or a lopsided decision win for Gillespie.

Second Leg of Parlay: Gregor Gillespie @ -160

Two Leg Parlay: 2.5 Units @ +161 Best Parlay Price (to Return 6.52 Units)

Jorge Masvidal vs. Nate Diaz

Main Event: Welterweight Bout for the “BMF Title” – 170lbs

Jorge “Gamebred” Masvidal – Record: 34-13-0 / #3 Ranked WW

Nate Diaz – Record: 20-11-0 / #7 Ranked WW

UFC 244’s main event is for the “Bad Mother F*****” Belt. I can’t say I personally like that this ‘title’ exists, or believe that it does, but if it’s what the UFC needed for them to make this fight a five rounder on a PPV, then I guess I’ll take it.

The contest itself is something I’ve actually flip-flopped on since hearing about it. Right from the moment Diaz called out Masvidal at UFC 241 I felt I was ready and waiting to bet on Masvidal for the fight, but since then I’ve now reversed my stance.

Initially I liked Masvidal as he’s been the more active competitor and he holds the better overall striking of the two. However, due to both fighters’ outstanding durability, and this being a 25 minute fight, I now like Diaz due to his greater volume and pressure. He lands on average 4.71 strikes per minute, which is 0.54 greater than Masvidal’s 4.17 (per ufcstats.com). And although this doesn’t stand out as being too significant, when you mix it in with his exceptional cardio, and preference to move forward, this does create a recipe for success against someone like Masvidal who likes to “take rounds off”.

We’ve now seen both guys on the scale, and each of them look in great shape. This means that we’re not only getting a Diaz that looks physically ready for the fight, but also one that is fully motivated and well prepared. We shouldn’t forget that he also has the minor height and reach advantages over Masvidal too.

Nate does also hold a fairly significant BJJ advantage, but assuming that people fighting for the “BMF belt” probably won’t be looking for takedowns, I think Diaz bettors can just put this into the back pocket and expect that it won’t play a role in the fight (unless someone gets dropped).

With all this being said, I like Diaz. He’s unquestionably the value side in this fight given the current line. I only really see this ending inside the distance if Masvidal lands something huge yet again, but this one should be headed for the scorecards. Take Diaz to win via decision, it’s by far his most likely method of victory, and his volume and pace should prove to be the differentiating factor.

Pick: Nate Diaz via Decision – 1 Unit @ +275 (to Return 3.75 Units)

Well that’s it for my picks for UFC 244!

For all those betting the fights, best of luck to you. We’ll hopefully be in for one hell of an event if it lives up to the hype! Come back next week for my UFC picks for UFC on ESPN+ 21: Zabit vs. Kattar!

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By Christian Broughton

Article Author


A former sportsbook trader with a passion for mixed martial arts. If there is value to be found then Christian is the man to find it.


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