Every WWE Money In The Bank Winner Ranked From Worst To Best

For when a golden ticket becomes a silver medal, and EVERYTHING in between.

Brock Lesnar
WWE

When Andre The Giant first teased the heel turn he was about to spring on Hulk Hogan, he did so by placing his giant hand towards the WWE Champion and simply noted how three years was a long time.

He wasn't wrong, and nor was his intent alongside new manager Bobby Heenan. The two had colluded to try and stun 'The Hulkster' into shock so they could bring that three years crashing down so hard that it'd hurt inside. Three years was a lifetime in 1987, and that was how tough it was to even get near a title shot at the singular pay-per-view event in the calendar.

By comparison, Money In The Bank is the reflection of modernisation. Instant gratification promised through surviving but one gruelling battle. A shortcut to the very top taken by the vast number of people invited to try the route, and it's that we've been made to look on at for nearly twenty years to ensure that a title tyranny quite like Hogan's simply wouldn't stand in the modern age.

Or wouldn't had it not been for Roman Reigns' post-2020 rebirth as 'The Tribal Chief' anyway. Which perhaps explains a couple of the early mishaps in this list...

28. Otis

Brock Lesnar
WWE.com

Time With Contract: 168 Days

Count the terrible things attached to Otis' cursed time with the Money In The Bank contract.

He "won" the thing by accident when AJ Styles was too much of a klutz to hold on to it at the climax of one of the worst matches in company history. 2020's cinematic variant was a risible and artless failure, much like Otis' actual run when the creative team lost interest long before they'd considered how the Heavy Machinery man might actually benefit from it.

RIP to that tag team too - Tucker turned heel on his partner to rip the prize away before Otis even found the time to turn funny into money. After several months of barely any teasing or direction, the future Alpha Academy man lost his best friend and his briefcase in a match against The Miz, and has been nowhere near singles glory since.

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Michael is a writer, editor, podcaster and presenter for WhatCulture Wrestling, and has been with the organisation nearly 8 years. He primarily produces written, audio and video content on WWE and AEW, but also provides knowledge and insights on all aspects of the wrestling industry thanks to a passion for it dating back over 35 years. As one third of "The Dadley Boyz" Michael has contributed to the huge rise in popularity of the WhatCulture Wrestling Podcast and its accompanying YouTube channel, earning it top spot in the UK's wrestling podcast charts with well over 62,000,000 total downloads. He has been featured as a wrestling analyst for the Tampa Bay Times, GRAPPL, GCP, Poisonrana and Sports Guys Talking Wrestling, and has covered milestone events in New York, Dallas, Las Vegas, Philadelphia, London and Cardiff. Michael's background in media stretches beyond wrestling coverage, with a degree in Journalism from the University Of Sunderland (2:1) and a series of published articles in sports, music and culture magazines The Crack, A Love Supreme and Pilot. When not offering his voice up for daily wrestling podcasts, he can be found losing it singing far too loud watching his favourite bands play live. Follow him on X/Twitter - @MichaelHamflett