Damian Priest's contract with WWE expired while he held the Money in the Bank briefcase

The Raw wrestler won the big briefcase without having a valid contract with WWE

Damian Priest
Photo Credit: WWE.com
Sebastián Martínez
Sebastián Martínez
Published 09/20/2026

Damian Priest was walking through WWE with the Money in the Bank briefcase in 2023, Judgment Day behind him and a big push ahead, but apparently he was missing something quite important: his contract with WWE had expired. Sean Ross Sapp dropped that bomb during a Fightful Select Q&A while analyzing how the WWE contract process changed during the TKO era.

The conversation focused on former WWE executive Dan Ventrelle and how several talent agreements were allowed to dangerously approach their expiration date. Sapp explained that, although WWE seemed to like Ventrelle, some wrestlers were not exactly happy with how he handled negotiations. "What I know happened during the Dan Ventrelle era was that, first of all, there were a couple of wrestlers who just weren't happy with him, they didn't like the way he handled things. WWE seemed to be happy with him... but it was definitely a situation where some wrestlers felt that he downplayed some of their contributions and their importance to the company," said Sapp.

Then came Priest's case. Sapp pointed out that some WWE contracts were allowed to come extremely close to expiration or even expired, and Priest was apparently one of the most outrageous examples. "I specifically remember that some of the issues around that were that he let some contracts get very close to expiring or expire. I'm pretty sure Damian Priest was among them. Damian Priest won Money in the Bank, he had the Money in the Bank briefcase and his contract actually expired while he was holding the Money in the Bank briefcase," he revealed.

I don't think he was going to go anywhere else. He was, you know, in the middle of a big push, was part of Judgment Day and obviously they had some kind of main event plans for him, because that's where he ended up.

The astonishing thing is that things got so far in the first place. Sapp indicated that many people were not happy that WWE allowed Priest's contractual situation to reach the point where a wrestler carrying one of the company's most important weapons was technically out of contract. "But the fact that it got so far didn't sit well with many people. They felt that contract should have been done well in advance and definitely waited until the last moment for many wrestlers, and that's not the way they wanted to do business back then," he stated. Sapp added that WWE's negotiation process has continued to evolve since then: the company still takes some contracts close to the limit, but their approach to closing extensions has changed. "Sometimes they do it now and renegotiate and do things like that."