WWE Money in the Bank Winners Raise Questions as 'Future' Talk Stalls

Prior to Saturday night's Money in the Bank Premium Live Event, much of the post-SummerSlam "future of WWE" discussion had been centered around the men's division. Primarily, and for obvious reasons, Oba Femi and Bron Breakker.

WWE had the opportunity to shift that conversation over to the women's division with five brand-new world champions in waiting competing in the annual Women's Money in the Bank Ladder Match, but the creative team made the curious decision to place the briefcase in the hands of Tiffany Stratton for the second time in three years.

Stratton is far from the most tenured Superstar in the women's locker room, but as a former WWE Women's Champion, she represents the present more than the other female competitors inside New Orleans' Smoothie King Center. Four of them- Women's United States Champion Jacy Jayne, Lash Legend, Sol Ruca, and Lola Vice are still in their first year on the main roster.

WWE's future took a backseat to the present during Women's Money in the Bank

TIFFY 2X 💰@tiffstrattonwwe is once again Ms. Money in the Bank! pic.twitter.com/NpnMpNNh9X
— WWE (@WWE) October 10, 2026

It was actually Roxanne Perez, The Judgment Day's 24-year-old prodigy, who came into the women's annual ladder match with the most in-ring experience, with nearly twice as many career matches as Stratton.

Despite her status as a heel, the more than 13,000 fans in attendance at Money in the Bank were loudly cheering for Roxy to get her moment before Sol Ruca snatched it away with her finisher off the ladder spot that was inevitable from the moment she qualified for the match.

She's still young and has a very bright future ahead of her, but it just felt like it was time to elevate Roxanne up the card. The live crowd wanted her to win, and judging by the reaction online, many fans at home wanted Perez to win after watching her play the role of third wheel inside The Judgment Day for the last year of her career.

Stratton's victory marked just the first shocking outcome of the night, as Liv Morgan would go on to defeat Stephanie Vaquer and Becky Lynch in a triple threat match to win back her Women's World Championship.

What an interesting dynamic it would have been to have the Women's World titleholder and Miss Money in the Bank in the same group. The eventual Judgment Day breakaway and babyface turn for Perez, however, has now been pushed off to a later date. The focus instead is now on Tiffy Two-Time, who was thankfully okay after a scary fall onto the back of her head early in the ladder match, and whether WWE is going to run the exact same play as they did with Stratton's early 2025 cash-in.

It was the January 3 episode of Friday Night SmackDown last year when Stratton betrayed her friend and mentor Nia Jax by turning her 2024 Women's Money in the Bank contract into her first WWE Women's Championship.

An already anxious Chelsea Green being stabbed in the back by the very woman she was hoping would win the briefcase is a booking decision even the most casual wrestling fan could see coming from a mile away. Predictable doesn't mean bad; it just means predictable. Still, it would behoove WWE to really think outside the box about how they choose to execute both Money in the Bank contracts in the days, weeks, or months ahead.

Will Penta be a successful Mr. Money in the Bank?

The 2026 Men's Money in the Bank winner was far less questionable. Penta was one of the favorites to walk away with the briefcase, even though Bron Breakker was the MVP of the match and Je'Von Evans stole the show with one of the most insane spots you'll ever see in a professional wrestling match.

JE'VON EVANS SENT THROUGH THE AMBULANCE 🚨

OH MY GOD!! pic.twitter.com/yg22Mk6Mdv
— WWE (@WWE) October 11, 2026

The biggest issue with Penta winning the briefcase is timing. The man without fear is less than a month removed from his critically acclaimed world title fight against Roman Reigns, which left him begging for another shot at the Tribal Chief.

The OTC successfully retained his World Heavyweight Championship over LA Knight on Saturday, in what was arguably the best match of The Megastar's WWE career. Reigns appears to be unstoppable ahead of a rumored clash with Oba Femi in Saudi Arabia next April, and if Roman is the man Penta truly wants, then it begs the question of when and where this cash-in attempt will take place.

“I have a lot of ideas in my mind right now," Penta told the panel on the Money in the Bank post-show. "Something in my soul feels, Penta will soon become a World Champion. Very soon, I have a big surprise for everyone... “I know why Roman Reigns is the best in the universe, but now I have the best key in the world. Champs, watch your back.”

If Penta tries to use this key, as he called it, prior to WrestleMania 43, the odds are that he will be unsuccessful. Especially if he calls his shot in advance rather than taking the more often utilized "ultimate opportunist" route. If he waits until after the 'Showcase of the Immortals', he risks having to go up against The Ruler, who looks even more unstoppable than The OTC after knocking off "Big" Bronson Reed Saturday night.

Penta could turn his attention to the WWE Championship, but that's an already crowded field over on Friday Night SmackDown. The last thing the creative team needs to do is add another talent to that main event logjam on the Blue Brand that already consists of reigning WWE Champion Sami Zayn, CM Punk, Kevin Owens, Cody Rhodes, Randy Orton, Finn Balor, Gunther, Johnny Gargano and Drew McIntyre, who is rumored to be returning to television imminently.

While it may not have been as popular a booking decision, the better choice to walk away as Mr. Money in the Bank may have been Bron Breakker. The Unpredictable Badass and Oba Femi have recently launched what could be a years-long rivalry, and Breakker potentially playing spoiler to The Ruler's coronation at WrestleMania 43 would have been fascinating to watch unfold.

Three to six months from now, we could very well be singing the praises of the WWE creative team for the decisions they made Saturday night. As things stand right now, confusion clouds this writer's head following Money in the Bank, which was overall very enjoyable. Grading isn't my thing, but let's just call this incomplete until we see how things play out.

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