Predicting When Penta and Tiffany Stratton Will Cash in WWE Money in the Bank Contracts

The WWE Universe watched in awe Saturday night as Penta and Tiffany Stratton scaled their respective ladders and retrieved briefcases that provide them guaranteed championship opportunities whenever they see fit.

When might they choose to cash in and go for the championship gold?

Let's take a look with this preview of the next few months.

Tiffany Stratton

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Tiffany Stratton cashed in her first Money in the Bank briefcase on the first SmackDown of 2025, and there are few better ways for her to reignite Tiffy Time than by running it back.

It adds a sense of excitement and intrigue to the new year, and it allows SmackDown to produce a high-profile angle right out of the gate.

Stratton has gotten close to WWE Women's Champion Chelsea Green over the last two months, seemingly keeping her potential enemy close. That is a story that has legs, especially with Stratton possessing the briefcase, but there will come a time when WWE Creative has to pull the proverbial trigger or risk the fans growing tired of it.

Stratton kicking off the year with a cash-in, and heel turn, gets 2027 off to a hot start for the SmackDown women's division. It also puts Green in a position to make a run toward a rematch for the gold, whether that is before or at WrestleMania.

Penta

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Assuming the plan remains for Oba Femi to challenge Roman Reigns for the World Heavyweight Championship at WrestleMania 43, and to have a long run after, the window for Penta to cash in his briefcase is smaller than it is with Stratton.

The luchador would seemingly have between now and the Royal Rumble to take his shot at dethroning Reigns and avenging his loss on September 14 in Mexico City.

An excellent setting would be Survivor Series, where Penta could take advantage of a grueling War Games match between The Bloodline and the 946 by rocking Reigns with a Mexican Destroyer, pinning the OTC, and capturing the top prize on the Raw brand.

He can then hold onto it for two or so months before dropping it back to Reigns and allowing the company to roll out the creative for the biggest match in recent WWE history.

The alternative is Penta cashing in on Oba Femi and having about as much success as anyone else has against The Ruler en route to his run as the company's new face.