Five most memorable WWE Money in the Bank custom briefcases

Tiffany Stratton and Penta emerged as the women's and men's Money in the Bank winners at WWE's Money in the Bank 2026 in New Orleans on October 11, bringing renewed attention to the tradition of customised MITB briefcases. Over time several winners have commissioned distinctive cases and some of those designs have become notable in their own right.

Customising the Money in the Bank briefcase has become a way for superstars to extend character and momentum beyond the ladder match itself, and this piece examines five of the best such designs. The selections range from gifts that replaced destroyed originals to personalised props unveiled on subsequent television shows, covering examples from 2006 through 2026.

Tiffany Stratton first received a custom briefcase during her initial Money in the Bank ladder match in 2024 when Nia Jax, described as her then-friend, gave her a replacement after the original case had been destroyed on SmackDown a week earlier. Jax's gift was a pink briefcase with a strap presented to "Tiffy Time." Stratton later won the 2026 MITB ladder match as well.

Rob Van Dam's rise toward the main event began with his 2006 Money in the Bank victory at WrestleMania 22, and he later introduced a personalised MITB briefcase painted blue and green bearing his RVD initials and logo. That presentation and the momentum it represented ultimately led to him becoming WWE Champion.

Naomi claimed the Women's Money in the Bank in 2025 following a major heel turn that generated significant momentum and went on to capture the Women's World title the same year. She reflected that run in her briefcase by painting it black, applying her Caution tape, and even using it as luggage.

Penta's performances culminated in winning the 2026 Men's Money in the Bank ladder match in New Orleans on October 11, and on the following RAW he revealed a new black-and-red design. The masked luchador's case featured the words "Dinero En El Banco," his logo, and pyrotechnics that accompanied it during his entrance.

Brock Lesnar's 2019 appearance in the Money in the Bank ladder match became memorable when he entered at the last minute and unhooked the briefcase, later revealing it as a custom boom box. Lesnar used that prop to appear dancing to different music on numerous occasions after his win initially drew negative reactions.

Stratton's 2026 victory made her the second woman to win the briefcase twice, and Penta's win made him Mr. Money in the Bank following a setback in Mexico City against Reigns the previous month. With Stratton now a two-time holder, the article notes it will be interesting to see whether she brings another custom design.