WWE Money in the Bank 2026 Men’s Ladder Match predictions

Money in the Bank is this Saturday night in New Orleans’ Smoothie King Center, bringing us a big night of pro wrestling spectacle, WWE-style. Oct. 10’s premium live event has a lot of big matches on it, including the Ladder Matches which give the show its name.

Our regular motley crew of pro wrestling blowhards will be making predictions about every match on the card, and we’re joined by our first Guest Picker: SBNation’s Matt Warren. When he’s not dreaming about the one, true sport of professional wrestling, you can find Matt slumming it covering some upstart promotion called the National Football League in our NFL Feed. Check it out for some great conversation about this weekend’s games there, and if you are a “sportsball” fan, follow your favorite NFL team(s) while they are there. And with the SBNation app, it’s easy to swipe between communities — from Cageside to and your other teams or sports.

Here, we’ll focus on the battle for a briefcase containing a pick-your-spot shot at one of the main roster top Men’s belts. Yesterday, we did the same for the Women’s Money in the Bank match — you can join that conversation here. We’ll be digging into the World Heavyweight, Women’s World title and other matches tomorrow. But we wanted to spend more time gabbing with y’all about those Ladder Matches, seeing as they’re what led to the creation of this event — and pushed it to “Big 4/5” status.

Let’s talk dudes climbing for cases.

PREDICTIONS FOR THE 2026 MEN’S MONEY IN THE BANK LADDER MATCH

Bron Breakker vs. Je’Von Evans vs. Trick Williams vs. Penta vs. CM Punk vs. Kevin Owens

Who claims the case?

Geno Mrosko: Based on recent momentum, you have to think Penta. But I’m not sure if they’re thinking like that right now. If it’s me with the pencil, I’m probably going with Trick Williams because I think he can translate to the main event scene seamlessly tomorrow, literally. But there are only going to be so many chances to give a guy like Bron Breakker the opportunity to work his way back to breaking through to the top, and this is the big one they can take advantage of now. So do it. Pick: Bron Breakker

Sean Rueter: Something tells me WWE won’t be able to resist the pull of nostalgia here… Pick: CM Punk

Kyle Decker: I think creative didn’t even realize just how much they had in Penta until his big match with Roman Reigns the other week. Now that they do, I predict they give him the briefcase to go all the way with him. Pick: Penta

Claire Elizabeth: I will never stop banging this drum until they do the deal— Je’Von is The Guy, strap him to the rocketship and let him fly! …er, more than he does already, that is. Pick: Je’Von Evans

Cain A. Knight: If Kevin Owens is putting his surgically repaired neck on the line in a chaotic ladder match with so many risky and dangerous spots, then he damn well better be booked to win it. I don’t think Roman Reigns is dropping his world title before SaudiMania, so it makes more sense for the MITB winner to come from SmackDown. That doesn’t help the case for current favorites Breakker or Penta to win. Pick: Kevin Owens

Marcus Benjamin: I’m going with who I think is the hot hand right now, and who gets a big boost holding on to that briefcase, even if they don’t get the championship. Pick: Je’Von Evans

Jon Velez-Jackson: Well, we know it won’t be Je’Von plucking the briefcase from the hook, no matter how much fun he is to watch. Bron winning makes a lot of sense, but so does maybe Kevin Owens, in order to challenge Sami Zayn. Yet, I would like to think Triple H realized something when he saw Penta’s performance (and the crowd’s reaction) in his match against Roman Reigns. Paul Heyman knows it: Penta has the It Factor, and WWE would be wise to strap a rocket to him. Pick: Penta

Josh Jagler: CM Punk and Kevin Owens have recently been in the title picture and don’t need a briefcase to be considered legitimate contenders. I think their presence in this match will cancel each other out. Je’Von Evans and Penta just beat the tag team champs on Raw this week, leaving me to think they could be winning tag gold together. That leaves me with Bron and Trick. If I squint and turn my head sideways, I can see a scenario where Bron wins, cashes in quick, and eventually drops the title to Oba, that kind of hot-shotting isn’t something we see often. More likely, we see some lemon pepper stepping up the ladder, whooping that trick, and grabbing the briefcase. Pick: Trick Williams

Matt Warren: We know that WWE has put this on established stars over the last few years. Putting the briefcase with Punk or Owens would really not tell a compelling story unless Owens is going to cash in at Crown Jewel over Sami. I don’t see that happening. Penta’s big push already got him a title shot and we’ve seen the higher ups resist the most recent flavor in these matches. I am not sold on Je’Von Evans jumping a lower-level championship to the main event. Trick Williams has gold and can wait a little, but Bron really needs this W. He couldn’t conquer Oba Femi on his own, so this is a way to get him into the title scene even if he doesn’t cash in for a while. Another loss after dropping matches to Seth Rollins, Punk, and Femi in 2026 would really kill his momentum. Pick: Bron Breakker

When will they cash in, and on who?

Geno Mrosko: The thing about Breakker winning the briefcase is I think they play the long game with it if he does. I’ll hate that, because they won’t be able to help themselves and will make it too much of a focus of his character but there’s just no room for a cash in for, like, maybe six months? I’m talking post-WrestleMania next year. By that point, there’s no telling what the landscape will look like. I’ll take a guess here. Pick: Oba Femi on the Raw After WrestleMania

Sean Rueter: As it has in the past, the case allows Punk to play some mental games with people. Who better than that t-shirt-wearing Canadian and his lil red-headed buddy. Pick: On Kevin Owens after he beats Sami Zayn for the title at Royal Rumble

Kyle Decker: I’m calling an LA Knight win (crazy I know), but I don’t think it’s long. I think he wins the title due to the 946. And then, the following Monday, 946 take Knight out out of principle and Penta picks the bones. Pick: LA Knight on Monday Night’s Raw

Claire Elizabeth: Well since I started off way out in speculation land it can only be more fantasy booking from here, so let’s say the WWE Championship goes from Sami to Kev to GUNTHER by sometime in the post-Mania season and uh-oh here comes Je’Von with the briefcase… Pick: GUNTHER at the April 30, 2027 SmackDown

Cain A. Knight: There’s nobody better in WWE to torment Sami Zayn with the MITB contract than Kevin Owens, and he deserves a title run while he can still go in the ring. But wouldn’t it be a little sweeter if he instead cashes in on Corporate Man Punk? Pick: CM Punk at Wrestlepalooza

Marcus Benjamin: He will cash in but I don’t see him winning the title. If only because when he cashes in will show his age and that he still needs to mature. Pick: Je’Von Evans at Survivor Series

Jon Velez-Jackson: Since I picked Penta, I think he will sneak in a cash-in against Sami, while Zayn is still feuding with Kevin and Punk. Pick: On Sami Zayn at Survivor Series.

Josh Jagler: Trick Williams has been interacting with many of SmackDown’s main event stars in recent months, which I think has foreshadowed a run with the WWE’s top prize. Since Triple H is believed not to be a huge fan of the briefcase gimmick, I bet he tries to get at least one cash-in out of the way quickly. What better way to do that than to have Trick cash in on the ol’ Gingerbread Man himself? Pick: Sami Zayn on a November episode of SmackDown

Matt Warren: Oba Femi vs Roman Reigns is a grueling endurance test for a guy who has never had to go long in a match on the main roster. Paul Heyman is at ringside waiting to align himself with the winner. Femi wins but sells being spent. Breakker comes out to wipe away any doubts about his standing in the company. Pick: Oba Femi at Wrestlemania

Will their cash-in be successful?

Geno Mrosko: Yes, and it’s going to piss everyone off so very, very much. Pick: To a chorus of boos heard round the world

Sean Rueter: In this fantasy booking scenario I’ve cooked up in my head, I want to say no… that Sami recovers, realizes what is happening, and sides with KO to screw Punk’s cash-in. But my heart knows that’s not happening. So… Pick: (sigh) yep

Kyle Decker: Yes. Penta is going to be their next big Mexican star they’ve been looking for for ages now. Roman will go feud with Royce Keys & gang. LA Knight fans will be sad. Pick: And New…

Claire Elizabeth: C’mon I didn’t come this far to make my guy a loser, did I? Pick: Je’Von Evans, freshly minted WWE Champion the day after he turns 23

Cain A. Knight: Kevin Owens should absolutely get a run with the WWE championship while he can still go in the ring. Pick: Yes

Marcus Benjamin: Nope. But he learns more from losing than he does from winning. At least for now. Pick: Nope.

Jon Velez-Jackson: Yes, and the crowd in Houston will love it. Pick: Yes, congratulations to the new Undisputed WWE Champion Penta

Josh Jagler: Yesterday I predicted that Roxanne would be the first woman to ever lose a briefcase cash-in. I just don’t see both briefcase holders losing in the same year, so I think we could see a Trick Williams WWE Title run before 2026 is up. Pick: And new WWE Champion, Trick Williams!

Matt Warren: Maybe Bronson Reed helps wear out Oba Femi after a tough match against Roman Reigns before the briefcase is turned in to start the match, but Breakker closes Night 2 of Wrestlemania standing tall and sets up the biggest rivalry of the next decade by climbing the mountain. Pick: Bron Breakker beats Oba Femi and proves he’s mortal

That’s what we see happening in and after Saturday night’s Men’s Ladder Match. Chime in on our predictions, and give us your own in the comments below. Remember our Women’s Ladder Match picks are here, and we’ll see you tomorrow with more picks, and full coverage of Money in the Bank! If you haven’t already, get in on TooManyBirds’s community Prediction Contest in The Feed!