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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6.) Edge

Edge won the MITB Briefcase in the first ever Men’s MITB Ladder Match at WrestleMania 21 in 2005 and cashed in at New Year’s Revolution 2006 to win the WWE Championship from John Cena after Cena retained the WWE Championship in an Elimination Chamber Match against Kurt Angle, Shawn Michaels, Kane, Carlito and Chris Masters.

Edge won his second MITB Briefcase after defeating Mr. Kennedy on the May 7, 2007 episode of Monday Night Raw. He cashed in the next night on the May 8, 2007 episode of SmackDown to win the World Heavyweight Championship from The Undertaker after an attack by Mark Henry.

Vince McMahon announcing his MITB cash-in was innovative but took away from the shock value of his cash-in. Nonetheless, Edge made MITB memorable by taking short cuts like a true heel MITB holder, capitalizing on the beaten down John Cena and later The Undertaker, and making everyone cringe when he walked off into the sunset with Matt Hardy’s ex girlfriend, Lita.

Alongside Lita, he had entertaining segments with the MITB Briefcase as well as entertaining teased cash-ins before cashing in successfully. He went on to become a megastar and legend in the WWE after his two successful MITB cash-ins.

Shock Value: 3.5 Stars (B-)

Memorability: 4.0 Stars (B+)

Booking Quality: 4.0 Stars (B+)

5.) Rob Van Dam

Rob Van Dam won the MITB Briefcase in the Men’s MITB Ladder Match at WrestleMania 22 in 2006 and announced his cash-in at One Night Stand to win the WWE Championship from John Cena.

It is very rare for an announced cash-in to end successfully (e.g. John Cena, Braun Strowman, Damian Sandow), but RVD is that one-of-a-kind superstar who actually pulled it off.

Although announcing his MITB cash-in advance took away from the shock value of his cash-in, the unexpected finish with Paul Heyman running from the crowd to make the three-count for RVD was epic, made up for the shock value, and was quite suitable for a Paul Heyman Guy.

It’s hard to forget this cash-in and the WWE Universe has Paul Heyman to thank for the added touch.

Alongside Paul Heyman, RVD went on to become a one of a kind, high-flying, legendary WWE superstar after his impressive MITB cash-in. He is now a WWE alumnus, but that MITB run was historic because it was the first and last time a superstar announced his MITB cash-in advance and did so successfully.

Shock Value: 4.0 Stars (B+)

Memorability: 4.0 Stars (B+)

Booking Quality: 4.0 Stars (B+)