5 WWE Stars Who Deserved to Win Money in the Bank But Never Did

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Here are five stars who deserved to win the Money in the Bank:

#5. Chris Jericho

Chris Jericho was the visionary who conceptualized the Money in the Bank ladder match at WrestleMania 21. However, he never got the opportunity to win the coveted briefcase that he helped invent. There is no doubt that Jericho was the absolute master class of elevation throughout his storied career in WWE. He was capable of carrying World Championship feuds entirely on the mic while putting great matches inside the ring.

During his 2008 and 2012 returns, Y2J was riding on red-hot momentum and had every tool to become the Men’s Money in the Bank winner. He could have executed brilliant, cowardly cash-ins, weaponizing the contract to steal championships. Rewarding Chris Jericho with a Money in the Bank victory would have served as the ultimate tribute to his creativity, as he was one of the most deserving names to win the coveted briefcase.

#4. Shelton Benjamin

Shelton Benjamin was one of the most promising names in the early years of the Money in the Bank ladder matches. He absolutely deserved to have won the briefcase during that period, as the 51-year-old was riding on red-hot momentum back then. Year after year, Benjamin single-handedly stole the show with breathtaking stunts that left the WWE Universe in absolute awe.

Despite consistently delivering iconic, career-defining moments, he never actually got his true reward. WWE should have handed Shelton Benjamin the Money in the Bank briefcase, as it could have elevated him to stardom. Doing so would have acknowledged his years of hard work and given him a world title push that Benjamin was overdue for in the Stamford-based promotion.

#3. Christian

If there’s a list of WWE’s most criminally underrated utility players, Christian would have been somewhere at the top. He possessed an elite combination of technical wrestling, psychological depth and elite mic work, making him a perfect fit to become the Money in the Bank winner. During his prime years, the Canadian proved he could anchor the main event scene seamlessly.

He was a master technician, often referred to as Captain Charisma. Christian’s strategic mind would have thrived if he had the Money in the Bank briefcase. Winning the contract would have provided him with the definitive transitional catalyst to solidify his main-event status organically. Unfortunately, the MITB briefcase always remained out of his grasp.

#2. Mustafa Ali

Mustafa Ali was inches away from having the biggest moment of his WWE career in 2019. He was scheduled to win the Money in the Bank briefcase that year, but Ali got robbed at the eleventh hour due to a change in plans. Just when the 40-year-old was inches away from retrieving the briefcase, Brock Lesnar showed up and snatched his moment away from him

Well, Mustafa Ali’s Money in the Bank moment being squandered in 2019 is one of the most glaring missed opportunities in WWE history. During that time, the 40-year-old was gaining popularity among fans. Winning the contract would have served as the perfect vehicle to elevate him from a promising mid-card talent to a top-tier star. However, the company failed to capitalize on his momentum.

#1. WWE star LA Knight

LA Knight not winning the Money in the Bank yet is perhaps the biggest missed opportunity in recent history. The Megastar was on a meteoric rise in the company during 2023, with him receiving Stone Cold-level reception from the WWE Universe all around the country. Every time Knight grabbed a microphone, the entire arena erupted in a frenzy, echoing his catchphrases and treating him like the biggest babyface in the industry.

Winning the 2023 Money in the Bank ladder was the perfect storybook payoff for LA Knight that could have cemented his status as a true top-tier star. The atmosphere was electric and the stage was set, yet WWE did not pull the trigger. Fans waited year after year after year, but Knight’s Money in the Bank moment never came. Despite having the perfect setup in 2023, 2024, and 2025, Triple H miserably fumbled the opportunity to give The Megastar the briefcase.

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