5 perfect MITB cash-in opportunities that Damian Priest wasted on WWE TV

It has been over eight months since Damian Priest won the Men's Money in the Bank ladder match. It's high time he cashes in the contract on a WWE champion.

Over the past two decades, fans have witnessed numerous failed Money-in-the-Bank (MITB) cash-ins. Even though the contract allows its holder to exercise it at any time, regardless of what state the titleholder is in, some WWE Superstars still couldn't get the job done.

To avoid such a setback, Damian Priest has been extra careful not to make any hasty decisions. However, the problem with his extended possession of the MITB briefcase is the fact that he has had several opportunities to cash it in that have been squandered.

That said, let's take a look at five instances of The Judgment Day member being handed a perfect cash-in opportunity on a silver platter, only for him to let it go.

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#5 On Seth Rollins on RAW (March 4, 2024)

As one-half of the Undisputed WWE Tag Team Champions, Damian Priest can appear across all WWE shows. But WWE RAW is the brand that he is a full-time member of.

Lucky for him, the red brand has its own world champion: Seth 'Freakin' Rollins, who takes pride in showing up every single week. So, it's no surprise that Señor Money in the Bank has found Rollins in a vulnerable spot on more than one occasion. Despite that, he still doesn't have the big gold belt around his waist yet.

On the latest edition of Monday Night RAW, Priest had the ultimate opportunity to dethrone The Architect. Having recently been medically cleared, the World Heavyweight Champion sprang into action to defend Jey Uso from his brother, Jimmy.

In doing so, Rollins took his eyes off his WrestleMania 40 opponent, Drew McIntyre, resulting in a surprise Claymore Kick. The show ended with The Visionary laid out in the middle of the ring, with no sight of Mr. Money in the Bank.

#4 On Logan Paul on WWE SmackDown (February 23, 2024)

In 2022, Austin Theory became the first WWE Superstar in history to cash in the MITB contract on a mid-card title. He exchanged the coveted briefcase for a failed shot at the US Championship.

Therefore, one would expect Damian Priest to keep his eyes on the mid-card titles too. And if he's doing that, his observational skills have huge room for improvement, because he certainly could've been the US Champion by now.

During the WWE Elimination Chamber 2024 go-home episode of WWE SmackDown, Priest was in the building to confront the #1 contenders for the tag team championship, Pete Dunne and Tyler Bate. Also in the house was the reigning US Champion, Logan Paul.

At the end of the night, Logan Paul ate a devastating spear from Bobby Lashley during a six-man brawl. The only man standing at the end of said brawl was Randy Orton. Given The Viper's laid-back demeanor, it's unlikely that he'd have saved The Maverick from being the victim of a MITB cash-in. But the briefcase holder decided to no-show yet again.

#3 On Gunther on WWE RAW (November 20, 2023)

Recently, The Judgment Day and Imperium came face to face in the ring and exchanged some heated words. During the segment, The Ring General took notice of Damian Priest's MITB briefcase.

Therefore, it's fair to assume that Gunther will now be wary of Priest trying to sneak up on him and try to take the Intercontinental Championship away. That would hinder The Archer of Infamy's chances of succeeding in his cash-in attempt, if he chooses to go after the IC Title.

A few months ago, though, Priest did get a chance to catch Gunther off-guard. It was the November 20, 2023, edition of WWE RAW. The Ring General had an in-ring segment with The Miz, which ended with A-Lister laying The Imperium leader out with a low blow and a Skull-Crushing Finale.

Given that Gunther wasn't even dressed for a fight that night, Señor Money in the Bank could've grasped the golden opportunity and pinned the Austrian superstar. But it turned out he didn't want any distractions ahead of his group's War Games match at WWE Survivor Series.

#2 On Seth Rollins on WWE RAW (September 18, 2023)

Damian Priest has tried cashing in his Money in the Bank contract on Seth Rollins multiple times, only to get interrupted. Nevertheless, he has also overlooked countless fantastic opportunities.

During The Visionary's heated rivalry against Shinsuke Nakamura in the fall of 2023, the latter was leaving the former lying in or just outside the ring on almost a weekly basis. If The Judgment Day member had played his cards right, he could have brought the World Heavyweight Championship to the group.

Arguably, his biggest fumble has to be not taking advantage of a battered Rollins on the September 18, 2023, edition of WWE RAW. During the episode in question, the World Heavyweight Champion and Nakamura got into a hard-hitting brawl ringside. The fight ended with The King of Strong Style reinjuring his rival's worn-out back.

With Rollins unable to even walk properly, an impromptu world title match would have almost guaranteed a new champion. Surprisingly, and for no valid reason, Damian Priest chose to wait for another occasion.

#1 On Roman Reigns at WWE Money in the Bank 2023

The 41-year-old wrestler could've joined the small list of WWE Superstars who cashed in their MITB contracts within 24 hours of winning it.

At the namesake premium live event last year, The Punisher of Judgment Day won the briefcase in the opening bout. The final match of the evening saw The Usos beating Roman Reigns and Solo Sikoa. That was the first time in over three and a half years that someone had pinned The Tribal Chief.

So, the window of opportunity was wide open for Priest to sneak in and pull off an even more impactful heist of the century than the one Seth Rollins accomplished at WrestleMania 31. On the night, The Bloodline was down to only two wrestlers, and Roman Reigns was totally shaken by his unexpected defeat, on top of having gone through a gruesome clash.

All Priest needed was to show up with his Judgment Day allies, attack Reigns and Solo, and walked away with the biggest prize in WWE today. However, he might have been too busy celebrating his iconic win, to see the opportunity that was staring him in his face.