5 WWE superstars who held the Men's Money in the Bank contract for the longest time

The Money in the Bank contract, introduced in 2005, is one of WWE's most intriguing and potentially career-altering concepts. Protected within a briefcase, often conveniently used as a weapon, MITB allows its holder to cash-in on any reigning champion at any time or place of their choice, for up to a year from winning the contract.

Given its clear strategic advantages, the contract has changed the careers of some of pro wrestling's top names, like Edge and Seth 'Freakin' Rollins. However, over the last two decades, fans have seen the MITB briefcase holders employ different strategies.

Some impatient individuals, like Kane and Dean Ambrose (now Jon Moxley), cashed in the same night they won the coveted briefcase. On the contrary, other holders were more cunning and calculated, playing the long waiting game for the ideal opportunity to seize their moment.

On that note, let's look at five WWE Superstars who held the Men's Money in the Bank contract for the longest time.

Note: Only those stars who successfully cashed in to win their intended titles have been considered in this article.

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#5. Sheamus waited more than 5 months to successfully cash-in on Roman Reigns at Survivor Series 2015

Sheamus is a sure-shot future WWE Hall of Famer. Among his many achievements, The Celtic Warrior became Mr. Money in the Bank in June 2015, a booking decision that cultivated much conversation and debate in the wrestling community.

Although a staple in the upper mid-card division with little fanfare, the Stamford-based promotion decided to make Sheamus the WWE World Heavyweight Champion at Survivor Series 2015. After Seth Rollins was forced to vacate the top prize, Roman Reigns won a tournament to win the title.

The Big Dog's celebration was short-lived, as Triple H came out to congratulate the champion, only to get attacked by Reigns. This allowed Sheamus to capitalize on the moment and successfully cash-in his MITB contract.

The Celtic Warrior waited 161 days to cash-in his Money in the Bank contract. To his credit, he couldn't have done so at a better time with a distracted champion and biased authority figure to add to the mix.

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#4. Dolph Ziggler infamously cashed in his MITB contract on the night after WrestleMania 29

Widely considered Dolph Ziggler's (now known as Nic Nemeth) career highlight, The Show-off successfully cashed in his Money in the Bank contract after waiting 267 days, on a battered and bruised Alberto Del Rio to win the World Heavyweight Championship on RAW after WrestleMania.

It was a special moment, a pay-off for years of commitment, perseverance, and passion. As soon as Ziggler's music hit, the crowd erupted in one of RAW's loudest ovations. An injured Del Rio fought back, but it was The Show-off's night as a Zig-Zag won him the World Title.

Unfortunately, while this should have been Ziggler's ticket to stardom, he suffered an untimely injury, keeping him off TV for much of his underwhelming reign. The current TNA star dropped the title back to Del Rio.

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#3. Seth Rollins planned and plotted "The Heist of The Century" at WrestleMania 31 for 9 months

From one memorable cash-in to another. Seth Rollins made history at WrestleMania 31, a show that was doomed to fail because of the controversial nature of the main event.

Roman Reigns, whose push has been rejected by the WWE Universe, was up against Brock Lesnar, who had just re-signed with the promotion. The two men fought tooth and nail in a hellacious bout that exceeded expectations.

The match reached a still-stop at the climax when both men were spent. Suddenly, Rollins' music hit, and Mr. Money in the Bank rushed to the ring. Mid-way through the match, Lilian Garcia announced that The Architect was cashing in, making the main event a Triple Threat Match.

After Reigns Speared Lesnar, Rollins capitalized and hit the Curb Stomp on his former Shield brother to win the WWE World Heavyweight Championship. Michael Cole called it, "The Heist of The Century," and few disagreed with the veteran commentator.

The threat of a cash-in was looming as The Architect had waited 273 days, but the facial expressions of the fans in attendance, Rollins' excitement, and Cole's commentary showed that no one genuinely saw it coming. It was brilliantly executed, and WWE must be given credit for avoiding disaster while creating a new top star.

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#2. Edge laid the blueprint with his well-executed Money in the Bank cash-in at New Year's Revolution 2006

It is impossible to discuss the Money in the Bank without mentioning Edge. The Hall of Famer won the first-ever MITB Ladder Match in a star-studded field at WrestleMania 21.

Edge waited 280 days to cash-in his contract, and it couldn't have been executed at a better time or place. The WWE Champion at the time, John Cena, had just retained the title in a grueling Elimination Chamber Match when Vince McMahon interrupted the celebration and introduced Mr. Money in the Bank.

Flanked by Lita, Edge Speared his way to the WWE Championship. The successful cash-in had major implications. It earned him the moniker of "The Ultimate Opportunist," catapulted him to superstardom, setting the stage for the Edge-Cena rivalry, and laid the blueprint for future cash-ins.

Edge showed future winners the way with his memorable cash-in. Rollins, CM Punk, Daniel Bryan, and others used The Ultimate Opportunist's strategy to win the World Title eventually. Therefore, the HOF's history with the MITB had a far-reaching impact.

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#1. Damian Priest waited the longest to cash-in his MITB contract

Señor Money in the Bank, Damian Priest, is the latest addition to this list, having won the World Heavyweight Championship less than three months ago.

The Archer of Infamy won the contract on July 1 in London last year. He waited 281 days, just beating Edge's long-standing record, to cash-in on a weakened Drew McIntyre, who had been assaulted by CM Punk at ringside, to become champion.

Priest's MITB run aroused much debate in the wrestling world. Some felt he had kept the briefcase hostage too long, and received many opportunities to cash-in, but when the dust settled, few were left complaining. El Campeón was smart and wise with the contract, and it paid off for him.