Failed cash-in plans for WWE Money in the Bank 2026: Three stars that could squander their opportunity with the briefcase

WWE

Given how exciting and potentially career-changing the Money in the Bank is, it’s always a disappointment when a WWE star fails with their cash-in attempt.

Only six stars in WWE history have been unfortunate enough to squander their shot, with the most recent example being Drew McIntyre in 2024.

With both cash-ins going smoothly in 2025 WWE may look to set up another unsuccessful attempt with one or both of this year’s winners.

Here are three WWE stars that could fail their Money in the Bank cash-in attempt:

Tiffany Stratton

Tiffany Stratton is one of the most notable Money in the Bank success stories of the past decade, as after winning the briefcase in 2024, she successfully cashed in early the following year and proceeded to hold the WWE Women’s Championship for 302 days.

On Saturday, Stratton will enter her second Money in the Bank match and will be seeking to replicate this success. While a win in Money in the Bank will make her the first female star to win the briefcase more than once across separate years, she could also earn the unfortunate distinction of becoming the very first woman to fail in her cash-in attempt.

Fans are anticipating Stratton will soon turn heel and go after her on-screen bestie Chelsea Green, catching the WWE Women’s Champion by surprise with a Money in the Bank cash-in. Although Green has gullibly believed that Stratton will be heading to Raw to target the Women’s World Title, perhaps she does actually have the foresight to see her friend’s real intentions, and can therefore prepare for Tiffany’s cash-in.

A failed attempt may be the best way to further motivate Stratton’s descent into a heel character, as she will be hell bent on getting the title off Green by any means necessary.

Bron Breakker

While Penta is reportedly considered the “heavy favorite” within WWE to win the men’s Money in the Bank briefcase, at the time of writing it is Bron Breakker who is most favored in the betting odds.

Breakker certainly needs the win more than any other, as his stock has taken a big hit in 2026 compared to where it was this time last year. But even if he does get over the line and wins the briefcase, he may find himself failing to successfully cash it in because Oba Femi is still out for blood.

“The Ruler” will be taking on Bronson Reed at Money in the Bank, and should he get past him one would imagine he will have his eyes on Breakker once again given that their first match at Sunday Night’s Main Event ended in a disqualification.

If Breakker attempts to cash-in Money in the Bank before he’s properly dealt with Femi he may pay the ultimate price, as the Nigerian could cost Breakker his shot and do a massive favor to his potential WrestleMania 43 opponent Roman Reigns in the process.

Roxanne Perez

Despite Tiffany Stratton having a strong case for a second Money in the Bank win, the more popular choice WWE could make would certainly be Roxanne Perez.

“The Prodigy” winning the briefcase would set up some seriously intriguing possibilities for The Judgment Day, with Liv Morgan not likely to take her underling’s win all that well; although Morgan may not actually get any time to think about Perez’s win before she’s already cashed-in and taken the championship.

The Women’s World Title is on the line in a three-way in New Orleans, with Morgan and Becky Lynch challenging Stephanie Vaquer for the gold. Providing this match takes place after Money in the Bank there is certainly a decent chance we see Perez pull of a same night cash-in, but will it be a success?

Morgan could very well sabotage the attempt, either blatantly or sneakily in a way that doesn’t appear to be her fault. This could then lead to Perez turning babyface and eventually winning the gold from Morgan later down the line, perhaps even at WrestleMania 43.

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