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

2.) Seth Rollins

With Corporate Kane’s help, Seth Rollins won the MITB Briefcase in the Men’s MITB Ladder Match in 2014 and cashed in at WrestleMania 31 to win the WWE Championship in a triple threat match against Roman Reigns and Brock Lesnar. Rollins was the first superstar to cash in at WrestleMania as well as before the championship match even ended.

Like Orton, Rollins sold out and joined the Authority. He did this after turning on the Shield and he needed to win the MITB Briefcase to take him to the next level because he never won the WWE Championship before that crowning moment.

He made MITB memorable by taking short cuts like a true heel MITB holder, cashing in at WrestleMania, and making the MITB Briefcase as prestigious as possible after holding it for ten straight months.

Thanks to his rivalry with Dean Ambrose, he had entertaining segments with the MITB Briefcase as well as entertaining teased cash-ins before cashing in successfully. The funniest segment involving his briefcase run was when Ambrose played a messy prank by having Rollins’ briefcase blow goo up his face.

Unfortunately, Rollins’ reign was cut short since he was injured and had to relinquish the title and miss the following WrestleMania, but his run with the briefcase and cash-in more than made up for it.

Shock Value: 5.0 Stars (A+)

Memorability: 5.0 Stars (A+)

Booking Quality: 4.5 Stars (A-)

1.) Dolph Ziggler

Dolph Ziggler won the MITB Briefcase in the SmackDown Men’s MITB Ladder Match in 2012 and cashed in on the Raw after WrestleMania 28 to win the World Heavyweight Championship from Alberto Del Rio after Del Rio won a 2-on-1 Handicap Match against Jack Swagger and Zeb Colter.

Unlike Mr. Kennedy, Dolph Ziggler actually retained the MITB Briefcase at WWE TLC 2012 against John Cena thanks to some nefarious assistance from AJ Lee. Just like James Ellsworth helped Carmella and Lita helped Edge as mentioned earlier, AJ Lee helped Dolph Ziggler keep the MITB Briefcase in his possession.

Ziggler needed to win the MITB Briefcase to take his career to the next level. He made MITB memorable by taking short cuts like a true heel MITB holder, cashing in on the Raw after WrestleMania with the biggest crowd pop of the millennium, and making the MITB Briefcase as prestigious as possible after holding it for ten straight months.

Alongside AJ Lee and even Big E later on, Ziggler had entertaining segments with the MITB Briefcase as well as entertaining teased cash-ins before cashing in successfully. His title reign was unfortunately very short but his run with the briefcase and cash-in more than made up for it. Thanks to the absolutely perfect shock value, memorability, and booking quality, he was truly the best Mr. MITB of all time.

Shock Value: 5.0 Stars (A+)

Memorability: 5.0 Stars (A+)

Booking Quality: 5.0 Stars (A+)