Will ‘Tiffy Time’ Cash in Her Money in the Bank Briefcase in 2026?

Money in the Bank took place at the Smoothie King Center in New Orleans, Louisiana. Many fans were surprised to see Tiffany Stratton win her second Women’s Money in the Bank briefcase. Stratton outlasted Sol Ruca, Roxanne Perez, Lash Legend, Jacy Jayne, and Lola Vice in their MITB Ladder Match. Many fans thought she was the least likely to win because she successfully cashed in her first briefcase in 2024. They thought someone like Perez or Ruca would win the briefcase. ‘Tiffy Time’ gives her another chance to fight for any women’s championship she chooses, anytime. Who will cash in on this year’s MITB briefcase? Will she cash in this year, or wait until next year to win another main-event women’s championship?

We can look at Stratton’s 2024 run with the MITB briefcase to get an idea of when she’ll cash it in. ‘Tiffy Time’ held the briefcase for 181 days before cashing in on Jax on the first episode of SmackDown in 2025. This showed that the former Women’s Champion was willing to wait for the perfect opportunity to cash in. The cash-in solidified her heel-to-babyface turn, since ‘The Irresistible Force’ had been manipulating and gaslighting her “friend” into thinking she could never become a world champion. Stratton teased the babyface turn for months, even performing a couple of “failed” cash-in attempts. WWE creative could lean back into this trope again, but for a heel turn instead of a face turn. They could also go the opposite way and have her cash in before the end of the year to unexpectedly win a women’s main event championship.

WWE has teased that Stratton will likely turn heel on her friend Chelsea Green. That makes sense, since she’s said in interviews that she prefers portraying a heel character. The Women’s MITB briefcase holder has taken a lot of damage over the past several months to protect her friend and help her win the Undisputed WWE Women’s Championship. ‘Tiffy Time’ has shown no disdain or regret for helping Green, but enough time has passed for WWE to expose those cracks slowly. If that happens, Stratton would likely blindside her friend and cash in on the fallen champ on the spot to become the new Undisputed WWE Women’s Champion. This would solidify a heel turn because ‘Hot Mess’ is a fan-favorite wrestler on an unexpected championship run fans have been pleading to see. This would also give the current Undisputed WWE Women’s Champion a believable long-term rivalry, despite WWE’s efforts to have her feud with Nia Jax and Nikki Bella. Stratton is likely to cash in this year if she chooses to cash in on Green.

WWE creative could throw their fans a curveball and have her cash in on the Women’s World Champion on Raw. SmackDown has a lot of heels on their women’s roster, and it’ll give ‘Tiffy Time’ new rivalries and matches to explore. Liv Morgan unexpectedly won the Women’s World Championship against Becky Lynch and Stephanie Vaquer, drawing heavy heat from the WWE Universe. Lynch and Vaquer seem headed down their own personal rivalry, regardless of whether the Women’s World Championship is involved. This takes those two out of the title picture for the foreseeable future. Stratton would solidify herself as a babyface by beating, arguably, the most unlikeable character on Raw. WWE fans would likely have to wait until 2027 if ‘Tiffy Time’ chooses to cash in her briefcase on a Women’s World Champion.