UFC 244 Predictions: Bleacher Report Main Card Staff Picks

The wait is almost over.

Ever since Nate Diaz called out Jorge Masvidal to crown the UFC’s biggest gangster, fight fans all over the world have salivated over the prospect of seeing two of the baddest dudes on the planet go head-to-head. 

Diaz returned to the Octagon in fine form in August delivering a blood-and-cuts brawler’s classic in a decision win over Anthony Pettis. It had been three longs years since Diaz last fought in the UFC, but he sure as heck didn’t fight like it. 

Masdival’s prominent rise from being the hardcore fight fan’s favorite to becoming one of the hottest MMA names in the world came after he delivered the fastest knockout in UFC history over previously unbeaten Ben Askren in July.

Now the two are set to tussle at Madison Square Garden in New York for the first-ever (and one-time-only) BMF belt the UFC created specifically for the event. 

It doesn’t get any bigger or better than that—except that even the undercard is packed full of even-looking matchups between stalwart competitors. 

There’s has never quite been anything like the UFC 244 pay-per-view card set for Saturday night in the Big Apple, so the only thing we could think of doing to honor such an outstanding slate of melees was to assemble the B/R MMA crew of Scott Harris, Kelsey McCarson and Jonathan Snowden to offer their official BMF predictions.

Scott Harris

A battle of two great MMA wrestlers, right here. It's not unfair to say Gillespie is unproven compared with Lee, but that doesn't make Lee the better fighter. Gillespie has been nothing short of dominant in his time in the UFC and before. Lee is on another level, but the onus is on the underdog to derail that dominant streak. Here's guessing he won't get it done, even if Lee will have a clear edge on the feet. That's how good Gillespie's wrestling has been.

Gillespie, unanimous decision

Kelsey McCarson

Gillespie is right about where Lee was five years ago. He’s an undefeated prospect that many people believe has a good enough skill set to reach the upper echelon of the sport. Lee almost did that, having fought for an interim title back a couple of years go. But he’s really struggled recently. Both fighters are strong wrestlers and have shown a consistent ability to put their opponents in some really tough binds. Gillespie has pretty much steamrolled everyone so far, and I think he’s a fighter who simply has everything headed in the right direction. I don’t think that changes this week. He won’t quite dominate Lee, but I do think he’ll do enough to stay unbeaten.

Gillespie, unanimous decision

Jonathan Snowden

I first met Kevin Lee shortly after he had committed fully to mixed martial arts, coming from Detroit to Las Vegas to immerse himself in the culture. The late Robert Follis, his coach, told me Lee had the potential to be a champion.

Follis didn't give those kinds of compliments lightly.

As yet, Lee hasn't quite reached the heights his coach predicted. He's given it his all and made it to the cusp of contention—but as the competition stiffened, he faltered, losing three of his last four.

As Kelsey points out Gillespie is where Lee was just a few years ago. The former NCAA champion is stepping up the competition for the first time himself. Lee, now 15 fights into his own UFC journey, is the veteran benchmark.

Time, as they say, is a circle.

Gillespie, unanimous decision

Scott Harris

The bloom is off the Wonderboy rose; Thompson has one winless in four of his last five, dating back to 2016. That could be a function of more than circumstance. His age (he's 36), his persistent and serious knee injuries, and his recent unwillingness to pull the trigger in live-action all are concerning. Luque's hyper-aggression could play in Thompson's favor. But you know what else? It also might not. Sound the upset alarms.

Luque, TKO, Rd. 1

Kelsey McCarson

Thompson’s ability to land from range gives him the stylistic advantage over Luque, a more aggressive stalker who throws lots of strikes and puts himself in harm’s way in order to do it. Thompson’s last win was two years ago over Masvidal in a fight where he showcased just how effective he can be when he’s at his best. He’s lost two in a row while Luque comes into things on a hot streak. Still, I like “Wonderboy” to right the ship and get back in the win column by forcing Luque into the kind of fight that favors Thompson.

Thomspon, unanimous decision

Jonathan Snowden

Thompson, like Kevin Lee, has lost three of four. Like Lee, his setbacks have come against elite competition. Unlike Lee, who has been handed a monster to try to tame, "Wonderboy" finds himself in a stylistically favorable matchup. This is his fight to lose.

Thomspon, unanimous decision

Scott Harris 

Ivanov is a very, very good fighter. You can be all the fan-favorite you want to be, but if you aren't ready to handle Ivanov's world-class grappling, you're going to have a long day, especially when you have suspect cardio, as Lewis does. Lewis is tough and hits as hard as anyone in the UFC, and he's a hell of a good quote. But Ivanov will show why he's a legit challenger at heavyweight, even if he has the public personality of a paperweight.

Ivanov, unanimous decision

Kelsey McCarson

Lewis has lost two fights in a row, but that came against Daniel Cormier and Junior Dos Santos, so there’s really no shame in that. Ivanov is coming off his best win against Tai Tuivasa and lots of people would love him to help add some depth to the heavyweight division. But Lewis is basically already the depth of the division, a crafty and explosive finisher who loses the very best big men but manages to beat just about everyone else most of the time.

Lewis, KO, Rd. 2

Jonathan Snowden

It's a Derrick Lewis fight, so basically any outcome is on the table. Only one thing is certain—there will be some heavy hands and some equally heavy breathing.

Lewis, KO, Rd. 3

Scott Harris

Gastelum's pressure will stifle Till's power striking game, and his clinch game will soften up Till for the big shot. Gastelum may have lost the 2019 fight of the year (to Israel Adesanya) but remember he's given the middleweight champ his toughest test to date in the UFC. Gastelum isn't going anywhere.

Gastelum, unanimous decision

Kelsey McCarson

There’s a good argument to be made that Till was cutting too much weight to be the best version of himself at 170 and that at 185 he’ll be much better than he’s ever been before. That’s basically what Gastelum has done since his big jump up the scale, a pressure-cooking mauler who keeps his foot on the gas for five minutes at a time. But Till has a super awkward style with lots of power behind it, so think he’ll manage at some point in the fight to run the ever-charging Gastelum into something hard enough to stop him for the upset.

Till, TKO, Rd. 2

Jonathan Snowden

These are two welterweights in a middleweight bout. Honestly, that's probably as healthy as mixed martial arts gets.

Gastelum is the biggest favorite in a card filled with pick-em style fights. Till may have the power to stop him, but does he have the wrestling acumen to stop a takedown? My (theoretical) money is on "no."

Gastelum, unanimous decision

Scott Harris

Below the pomp and circumstance, these are two well-rounded and inordinately tough fighters who are arguably in the best stretches of their pro careers. This is why you lace 'em up, and this is why you fork over for pay-per-views. I'll be fortunate enough to be at floor level in Madison Square Garden for this one. See you there.

Masvidal, unanimous decision

Kelsey McCarson

My eyes gravitate toward Masvidal because he’s a fluid enough striker and hard enough puncher who should be able to get the better of the action when Diaz inevitably pressures him. But my heart tells me that sometimes eyes can be wrong and that I shouldn’t pick against Diaz in a fight where something called the “BMF” title is on the line. To me, Diaz is the UFC’s original BMF gangster, and I think he proves it once and for all against Masvidal in a war that ends with both fighters bloody and spent.

Diaz, split decision

Jonathan Snowden 

The baddest of the bad, two fistic fight gods in a bout that promises to be one of the most frenetic spectacles in modern UFC history. These two men never disappoint. In front of the President and even the Rock himself, they will stake their claim on the only title that ever mattered in the world of combat sports. May the baddest man win.

Diaz, submission, Rd. 4