WWE Money in the Bank: Top 10 Greatest MITB Winners Of All Time

HOUSTON, TX - APRIL 5: CM Punk successfully reaches the top of the ladder during the Money In The Bank Ladder Mach during WrestleMania 25 at Reliant Stadium on April 5, 2009 in Houston, Texas. (Photo by Bill Olive/Getty Images)
HOUSTON, TX - APRIL 5: CM Punk successfully reaches the top of the ladder during the Money In The Bank Ladder Mach during WrestleMania 25 at Reliant Stadium on April 5, 2009 in Houston, Texas. (Photo by Bill Olive/Getty Images) /
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4.) CM Punk

CM Punk won the MITB Briefcase at WrestleMania 24 in 2008 and cashed in a few months later at the June 30, 2008 episode of Raw to win the World Heavyweight Championship from Edge after Edge was attacked by Batista. CM Punk’s title reign was not as memorable after this cash-in.

After not being booked in any main events as champion, he was disrespectfully written off TV with a Punt Kick by Randy Orton in the backstage area and ended up relinquishing the championship. However, Punk received a second chance at redemption a year later.

CM Punk won the MITB Briefcase at WrestleMania 25 in 2009 and cashed in a few months later at WWE Extreme Rules 2009 to win the World Heavyweight Championship from Jeff Hardy after Hardy defeated Edge in a Ladder Match to become the new World Heavyweight Champion. CM Punk had very memorable championship reign after this cash-in.

He was truly in his element with his Straight Edge gimmick as he branded himself as the first ever Straight Edge World Champion and continually shamed Jeff Hardy for having a terrible history of alcohol addiction and drug abuse. He even went on to end Jeff Hardy’s WWE career after defeating him in a Steel Cage Match on the August 28, 2009 episode of Friday Night SmackDown.

Like Orton, Punk won the MITB Briefcase as a a babyface and turned heel with his second MITB cash-in. Punk made MITB memorable by eliciting heel heat with his vindictive MITB cash-in against Hardy, creating the Straight Edge Society in what was one of the most controversial factions in WWE history, and later becoming the ‘Best in the World’ and the longest reigning WWE Champion (i.e. 434 days) in the PG era before leaving the WWE in 2014.

Shock Value: 4.5 Stars (A-)

Memorability: 4.0 Stars (B+)

Booking Quality: 4.5 Stars (A-)

3.) Bayley

Bayley won the MITB Briefcase at WWE MITB 2019 and cashed in on the same night to win the SmackDown Women’s Championship for the first time in her career from Charlotte Flair after Flair dethroned Becky Lynch to end the idea of ‘Becky Two Belts.’

As many remember, this MITB cash-in blew the roof off the place and was one of the most memorable babyface cash-ins. Many naysayers and critics tend to say that MITB Briefcases only work for heels but Bayley proved them wrong with his victory and cash-in.

Her cash-in had top-notch shock value, which kickstarted Bayley’s road to super stardom. After becoming a grand slam champion, she quickly put the SmackDown Women’s Division on notice by letting the women in the locker room know that she is at the top and they need to catch up.

Bayley made MITB memorable by receiving one of the biggest crowd pops for a babyface MITB victory and cash-in, elevating the SmackDown Women’s Division after turning heel, and later becoming the best SmackDown Women’s Champion in WWE history.

Shock Value: 4.5 Stars (A-)

Memorability: 4.5 Stars (A-)

Booking Quality: 4.5 Stars (A-)