This Saturday night, the world’s most famous arena hosts what could be the biggest pay-per-view of the year. UFC 322 at Madison Square Garden features not one, but two champions moving up in weight to chase history. Islam Makhachev. Jack Della Maddalena. Zhang Weili. Valentina Shevchenko. This card is stacked from top to bottom, and the Ringside Report Network crew isn’t holding back on their predictions.
And here’s where it gets interesting: Dave Simon is going against the grain in the main event. He’s picking the underdog. He’s picking Jack Della Maddalena to shock the world.
UFC 322 Main Event: Islam Makhachev (-290) vs Jack Della Maddalena (+215)
Dave Simon’s prediction: Jack Della Maddalena by decision or knockout
I’ve been back and forth on this fight for weeks now,” Dave explained on Thursday’s Ringside Report MMA. “Day to day, I didn’t know. But over the past couple of days, I’ve really dug into it, and I really think Jack Della Maddalena is going to win this fight.”
The reasoning is layered. First, there’s the size factor. Islam Makhachev has been talking this week about how comfortable his weight cut is, which might sound like a positive, but Dave sees it differently. If Islam isn’t really cutting weight, he hasn’t truly grown into a full-fledged welterweight. Jack Della Maddalena is a legitimate 170-pounder. He’s been defending takedowns from actual welterweights. Now here comes the 155-pound champion moving up, and he’s supposed to be the one to keep Della Maddalena down?
“It’s tough to keep Jack Della Maddalena down for welterweights,” Dave emphasized. “This is the 155 champ moving up to 170.”
Then there’s the age question. Islam Makhachev walks into the octagon at 34. Jack Della Maddalena is 29. Five years might not seem like much, but in MMA, it means everything.
Dave also questions the quality of Islam’s recent opposition. When was his last truly tested fight? The Renato Moicano bout in January was a 24-hour notice replacement. Before that, Dustin Poirier was on his way to retirement. The Alex Volkanovski fights were competitive, and Volkanovski is a featherweight. Charles Oliveira had many losses on his record before and after that title fight.
“Who is he really fighting?” Dave asked pointedly. “It ain’t Jack Della Maddalena.”
The Australian just beat Belal Muhammad, Gilbert Burns, and Kevin Holland in three consecutive fights. He’s a black belt in jiu-jitsu from Perth, and he’s riding an 18-fight win streak since losing his first two pro fights.
“The aura is starting to fade,” Dave said of the Dagestani fighters. “We saw with Marab and Umar that they’re not unstoppable. They can be beaten. And if anybody’s going to be figuring it out, it’s that camp out in Australia.”
At +215, Dave sees genuine value. Put $20 on Della Maddalena, and you’ll make $63 back. Put $100, and you’re making $315. But more than the odds, Dave believes in the matchup.
“Every man has his time,” Dave concluded. “Do you remember when Benson Henderson was the best lightweight in the world, and he went up to 170 and had trouble? It’s a big jump from 155 to 170. It’s a big jump.”
AJ D’Alesio’s counter-argument: Islam Makhachev wins at UFC 322.
AJ respects Della Maddalena’s scrambling ability but worries about his defensive grappling. When Belal Muhammad took him down three times, it raised concerns. Now bring in Islam Makhachev with that Dagestani training camp intensity.
“These guys live, breathe, and literally die for fighting,” AJ said. “You can see it through their training facility, their training camp, the way they train—two hours of power wrestling and grappling. There’s a freaking lake on the mat. And then after two hours of power training? They go out and hit the gym. That is insane.”
For AJ, Islam at 34 is still at his peak because of how these fighters train. He’s putting Islam in his parlay at -290.
UFC 322 Co-Main Event: Zhang Weili (+110) vs Valentina Shevchenko (-140)
Both Dave and AJ agree: Zhang Weili wins by decision
Another champion moving up in weight, and another case where Dave sees the underdog prevailing. Zhang Weili is the 115-pound strawweight champion, challenging Valentina Shevchenko for the 125-pound flyweight title.
“She never stops improving and seems to get better every fight, which is kind of nuts,” Dave said of Zhang Weili. “She’s been in the UFC since 2018, over seven years, and every single time you see her, even at 35 years old, she seems to be improving. We may see the peak on Saturday night.”
Zhang Weili is coming off five straight title defenses, including a dominant performance over Tatiana Suarez that made a highly-touted prospect look amateur. Her competitive will and pressure style should overwhelm Valentina.
“I think she just kind of runs through Valentina,” Dave predicted. “Like, just kind of punishes her. A lot of brutality, a lot of just raw strength. I think takedowns are going to be key, staying on top, pressure. That’s the key to Valentina. You don’t want to give her space to do some nice kicks. Pressure her.”
AJ pointed out a telling statistic: Valentina hasn’t won by stoppage since September 2021. Zhang Weili has multiple recent stoppages. The finishing power has shifted.
“You can see that there’s that step back,” AJ noted. “Which worries me, going up against Weili right now, who’s ready to knock her out. She doesn’t want to win by decision. You know that.”
Valentina Shevchenko has been the UFC flyweight champion since Zhang Weili came into the company. She’s been in the UFC since 2015, a decade of elite-level competition. Seven title defenses across two reigns. She took the belt from Joanna Jędrzejczyk back in 2018.
But at 37 years old, facing a Zhang Weili who’s still improving? The Ringside Report crew sees a changing of the guard.
Sean Brady (-140) vs Michael Morales (+110)
Dave and AJ both like Sean Brady
This could be a future title contender matchup. Michael Morales comes in at 18-0 with back-to-back knockouts of Neil Magny and Gilbert Burns. Sean Brady is 18-1 after guillotine-choking Leon Edwards in his last fight.
“Sean Brady is the real deal, man,” AJ said. “He’s like the All-American right now. If he can get Morales on his back, he can submit him.”
Morales comes from a serious fighting pedigree – both parents were Judo Olympians. But Brady’s grappling should be the difference-maker. Dave called him “Sean Sherk 2.0” for his relentless wrestling pressure.
With Brady from Philadelphia, he’ll have plenty of support at Madison Square Garden.
Leon Edwards (+140) vs Carlos Prates (-180)
Dave’s pick: Carlos Prates
AJ’s pick: Leon Edwards
Here’s where the crew splits. Dave thinks Leon Edwards is on his way down after getting submitted by Sean Brady. Prates has been knocking people out and is riding momentum.
“I think Leon is kind of on his way down,” Dave said bluntly.
AJ disagrees strongly. “It’s Leon Edwards, dude. Do not forget who he is. Every time we say something against Leon, he obviously proves why he was on top.”
Edwards has more experience and a former champion pedigree. Prates has that knockout power. The odds favor Prates, and for good reason – he’s only lost once since 2019.
Benoît Saint-Denis (-190) vs Beneil Dariush (+145)
Both pick: Benoît Saint Denis
The age gap is massive here. BSD is 29. Dariush is 36. In MMA, seven years is enormous.
“That’s huge for Benoît Saint Denis,” Dave said. “Twenty-nine to thirty-six is significant. It means something. It just does.”
Dariush is coming off a win, but AJ raised concerns about his mindset. “Every time he fights, he has some conversation about retiring. He’s more out than in. That’s what worries me with Dariush.”
BSD is coming off two straight victories and is on the rise in the lightweight division.
UFC 322 Featured Prelim: Bo Nickal vs Hiago Vieira
Dave’s pick: Bo Nickal by decision
Jiu-jitsu versus wrestling. Dave expects Bo Nickal to keep it standing and win an ugly three-round fight.
“When you see two grapplers, they just decide to punch each other, and it’s ugly,” Dave predicted.
The UFC 322 Parlay Breakdown
AJ’s Five-Fight Parlay (+1673):
- Islam Makhachev (-290)
- Zhang Weili (+110)
- Sean Brady (-140)
- Leon Edwards (+140)
- Benoît Saint Denis (-190)
Potential payout: $20 gets you $354.69
“That’s a beautiful payout, man,” AJ said. “And I think that can happen.”
Dave isn’t buying it. “I don’t like a couple of these fights. I don’t like Islam. I don’t like Leon.”
Dave prefers straight bets on the underdogs – Jack Della Maddalena at +215 and Zhang Weili at +110 – rather than putting them in a parlay.
Join Us Live Saturday Night
The Ringside Report Network is back for a UFC 322 watch-along party!
Dave Simon, Fred Garcia, and AJ D’Alesio will be live starting at 10:00 PM Eastern Time when the main card begins. This is the crew’s first watch-along since August, and they’re going all out for the biggest fight weekend of the year.
“This is a money card,” Dave said. “We’re partying on Saturday night for sure.”
Cannolis and espresso? Dagestani-style bear training? The guys are still figuring out the menu, but the analysis will be sharp, the banter will be real, and the fights will be legendary.
Where to watch:
- YouTube
- Rumble
- Twitch
- DLive
- Kick
Head to RingsideReport.net or find the Ringside Report Network on your preferred platform. Join the live chat, share your predictions, and be part of the community as we watch history unfold at Madison Square Garden.
Two champions moving up. Two potential upsets. One incredible night of fights.
UFC 322. Saturday night. 10 PM Eastern. Be there.
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