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

2. CM Punk

Brock Lesnar
WWE.com

Time With Contract Before Cash-In: 92 Days

Time With Contract Before Cash-In #2: 63 Days

The second man to win the Money In The Bank briefcase twice, CM Punk's glittering history with WWE's golden ticket produced two incredible cash-ins even if the first was something of a false dawn.

Claiming Edge's World Heavyweight Championship for Monday Night Raw as the 'Rated-R Superstar' threatened to take it to SmackDown after the 2008 Draft, Punk was unable to ascend to main events proper as a babyface titleholder.

It'd all be different when he repeated the feat a year later. After cashing in on Jeff Hardy following the 'Charismatic Enigma's brutal Extreme Rules war with (that man again) Edge, Punk liked the smell of his own farts a little too much. It fed a heel turn that was crucial for the character's growth and a programme that confirmed both men as bona fide draws atop the card.

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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