Predicting When Damian Priest, Iyo Sky Will Cash-in WWE Money in the Bank Briefcases

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Is Damian Priest eyeing an imminent Money in the Bank cash-in?Credit: WWE.com

Money in the Bank 2023 lived up to its billing as one of WWE’s most exciting and eventful pay-per-views all year, specifically with the crowning of a two new Money in the Bank winners.

Damian Priest opened the event outlasting six elite athletes to capture the contract in the men’s match. Later on in the evening, Iyo Sky reigned supreme over five of SmackDown and Raw’s finest female stars, including her Damage CTRL stablemate, to become Ms. Money in the Bank.

Both are first-time winners and among the favorites to secure the opportunistic briefcases. Now the countdown is on for when they’ll decide to cash in their guaranteed title shots and whether they’ll do so successfully.

The Money in the Bank has proven to be a one-way ticket to super stardom for some in the past and a death wish for others depending on how they’ve been booked. Priest and Sky deserve a chance to get over at a main-event level and continue climbing the ranks to the top of the card, but it’s all about the aftermath from here on out.

Let’s look at how WWE can properly follow up with the 2023 Mr. and Ms. Money in the Bank and attempt to predict when their cash-ins will come to fruition.

Why There’s No Need to Rush Either Cash-in

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Although the Money in the Bank contract offers its winners the option to cash in as early as the night of, that rarely makes for the strongest or smartest story.

In the near-20-year history of the concept, it’s happened more times than it arguably should have. It was a complete shock when Kane pulled off the unprecedented feat at the 2010 installment followed by Dean Ambrose six years later, but WWE has had every Ms. Money in the Bank since 2018 cash in either that same night or within 24 hours on Raw.

Needless to say, it’s become a tired trope with the women in particular and it’s imperative WWE stray away from making that same mistake for the foreseeable future.

Part of the appeal of Money in the Bank for fans is not knowing when and where the winners will cash in and on whom. Damian Priest and Iyo Sky are on opposite brands, so the company won’t run into the issue of two Superstars doing constant teases for months on end.

Playing the waiting game and having them hold onto their briefcases for a bit is the best course of action this year.

Racking Up Notable Wins and Continuing to Build Credibility

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WWE has fallen into a bad habit over the last decade of having Money in the Bank winners to lose a majority of their matches with the mindset that their bad booking will be forgotten about once they cash in their contract successfully.

They’ll sometimes attempt to avoid that by cashing them cash in immediately, and as previously noted, that isn’t always the ideal direction to go in, either.

As of now, Damian Priest and Iyo Sky are not completely ready to be a world champion and need to be built up more in the months to come before they can cash in successfully.

Of course, that’s assuming both breakout stars don’t have their sights set on midcard or tag team title gold, but they’re capable of thriving at the main-event level and that’s ultimately where they should end up, even if it isn’t necessarily soon.

Priest has lost a lot lately, and beyond Sky’s recent stellar match against Bianca Belair at Backlash, she hasn’t had many memorable performances on her own on the main roster due to being a part of Damage CTRL.

Their respective runs as Mr. and Ms. Money in the Bank should be spent giving them high-profile victories so fans can start to see them as the top talents they have the potential to be.

Breaking off on Their Own

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Before they can cash in to become champions, both Damian Priest and Iyo Sky must break away from the factions they belong to and establish themselves as singles stars on the rise.

Ideally, The Judgment Day would remain together as it’s practically perfect in its current incarnation, but that isn’t the story WWE is telling with them. Since the 2023 WWE Draft, there has been dissension within the group and all signs have pointed to Priest severing ties with Finn Balor.

Priest capturing the Money in the Bank briefcase while Balor fell short in his World Heavyweight Championship clash with Seth Rollins will only further drive a wedge between the two and cause Balor’s bad blood toward Priest to grow.

Meanwhile, Damage CTRL should have met its demise some time ago. A split was already being teased post-WrestleMania and Dakota Kai being out injured for the remainder of the year should expedite the process.

Bayley vs. Sky and Balor vs. Priest are logical programs to book soon, which will delay their cash-ins until they make more sense.

Potential Timetables for Cash-ins

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With all of the aforementioned timetables taken into consideration, neither Money in the Bank winner should be cashing in until the fall at the earliest. WWE will get two massive moments from the Money in the Bank cash-ins and should space them out accordingly.

As a member of the SmackDown roster, Iyo Sky will clearly be cashing in eventually on the WWE Women’s Championship, currently held by Asuka. That could change by the time Sky decides to challenge for it, but Asuka vs. Sky would be a fun and fresh feud, unless Sky takes the title from Charlotte Flair before the year comes to a close.

Priest’s path to the World Heavyweight Championship is slightly trickier, however.

WWE has established that the contract can be cashed in on midcard championships as well, so the idea that Priest could go after Intercontinental champion Gunther post-SummerSlam should not be discounted. The issue is that Priest has been a secondary champ before and the Money in the Bank briefcase should be what cements his status as a main-event player.

Seth Rollins is bound to have a lengthy reign ahead of him, and there’s a high chance Gunther will be the one to take it off of him. Priest vs. Gunther would work better as a world title program in early 2024.

No Money in the Bank holder has ever waited the full year and cashed in at the next installment of the event. While that’d be a cool concept to explore, it’s much more likely Priest and Sky will trade in their briefcases for title shots well before then.

Graham Mirmina, aka Graham “GSM” Matthews, has specialized in sports and entertainment writing since 2010. Visit his website, WrestleRant, and subscribe to his YouTube channel for more wrestling-related content.

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