Prettiest Cash In Ever (2025)

It’s not a coincidence that we’re fast-forwarding 10 years into the future to reach our next moment on the list. Before it was Tiffy’s time to cash in her Money In The Bank briefcase, 37 other superstars had done the same. There are only so many new ways to shock the WWE Universe, but Tiffany Stratton did just that.

On the January 3 episode of Smackdown, Tiffy’s friend Nia Jax defended her WWE Women’s Championship in a match against Naomi. As the contest was coming to a head, Stratton’s music hit, and she ran down to the ring holding her briefcase in one hand and the ref’s hand in another.

Despite the telltale signs of a cash-in, Tiffy instead hit Naomi in the head with her briefcase, aiding Jax to victory as she’d done several times previously.

We were swerved. And then, we were swerved again. As Bianca Belair went to check on Naomi, Jax attacked Belair and set her up for The Annihilator. Before she could execute it, Stratton whacked Jax with the briefcase, Belair followed up with a massive Kiss of Death and Tiffy took advantage, landing the Prettiest Moonsault Ever on Jax for the 1-2-3.

Betraying a friend—who was also the champion—with a cash-in is something we’d never seen. The soft face turn and exuberant crowd reaction helped solidify the moment in MITB lore.