5 Most Memorable Money in the Bank Moments

Dean Ambrose Cashes in on his Former Shield Partners (2016)

While not a high-flier like Kofi Kingston or Sin Cara, as physically imposing as Kane or Big Show, or as dramatic a cinderella story as Daniel Bryan or Dolph Ziggler, Dean Ambrose's balance of hardcore stamina and unpredictability are perfectly suited to the chaos of the Money in the Bank ladder match. Up against the absolute top talents of Chris Jericho, Kevin Owens, Cesaro, Sami Zayn and Alberto Del Rio, Ambrose emerged victorious to unhook the briefcase and claim the win in his hometown of Cleveland, Ohio.

But the Lunatic Fringe's moment in the spotlight wasn't over, as he cashed in his contract that very night against his former Shield Partners, defeating a weakened Seth Rollins for the WWE Title immediately after the Architect's win in a grueling match against Roman Reigns.

Seeing the title change hands between all three former Shield partners over the course of the main event, as well as Dean Ambrose wining the WWE World Heavyweight Championship contract and the title itself all in one evening, was an absolute shocker that gave fans exactly what they wanted.

Daniel Bryan's Surprise Win (2011)

The second edition of the MITB PPV hosted the legendary WWE Championship match between John Cena and the inusrgent CM Punk, but that didn't cast too much of a shadow on the eponymous match.

Along with the surprise winner Daniel Bryan, Sheamus and Kane propelled the match to a height that would be one of the benchmarks for ladder matches at the PPV to follow.

From the brutal moment when Sheamus powerbombed Sin Cara through a ladder, snapping it in half and sending the luchador out on a stretcher. He and Kane then together pulled off a Doomsday Machine on Daniel Bryan. But Kane would deliver poetc justice, choke-slamming Sheamus on a ladder he himself devised in the corner.

But Daniel Bryan's natural magnetism to the fans and perseverance ultimately lead to his emergence as the underdog winner, to the surprise and delight of fans.

The Big Show's Bad-Luck Ladder Burial (2010)

Perhaps the most entertaining moment in MITB history came from the very first Money in the Bank PPV in 2010. In a moment of ingenuity, the Big Show turned a ladder into a make-shift armored tank that would support his large frame. At one point, all 8 Superstars were climbing it. But the 500-pound giant would soon be entombed under a mound of ladders in no man's land, and Kane would instead emerge the final victor.

Paul Heyman Turns on CM Punk (2013)

The main event of Money in the Bank 2013 was a star-studded affair open only to former world champions. The 'All-Star Match of Legends' match, if nothing else, will be remembered for its star power. Six former World Champions – Randy Orton, Daniel Bryan, Sheamus, Christian, CM Punk and Rob Van Dam faced off for the briefcase.

At one point Daniel Bryan silenced all the competition in about a minute. But a late run-out by Curtis Axel put an end to Bryan's run in a volley of chair shots. But the surprises didn't end there as Axel, presumably sent by Paul Heyman to help his client Punk's chances, was disposed of by Punk himself with a GTS.

What followed was even more shocking, as Heyman turned from cheering Punk up the ladder to rolling into the ring and slamming the ladder into his client multiple times, drawing blood and knocking the Chicago native to the ground. The shocking betrayal ended Punk's night early, denying him the win and allowing Randy Orton to claim the briefcase.

Dean Ambrose Windmills a Ladder (2013) and Gets Back in the Fight (2015)

We began this list with Dean Ambrose and I'll give him the parting honors as well, for separate moments of defeat.

In the 2013 MITB match, Dean Ambrose made his mark against the tough competition of Wade Barrett, Cody Rhodes, Damien Sandow, Fandango, Jack Swagger & Cesaro. At one point, Ambrose made the surprising decision to put the ladder on his head and attack all competitors with a windmill. That is until Swagger and Cesaro got their hands on it, resulting in a hillarious spot where Dean repeatedly found his balance on the ladder until the pair used it to dump him out of the ring.

At MITB 2014, after what seemed like a withdrawal due to injury earlier in the match, Dean Ambrose charged back to the ring to foil Seth Rollins' plans of clinching the contract. But this show of determination was ultimately in vain as he was put down by the Kane, who stood guard while his Authority partner Rollins ascended and claimed the briefcase.

Honorable Mentions:

• Kofi Kingston hits Drew McIntyre with a Boom Drop Through the Announce Table (2010)
• John Cena & Dolph Ziggler win the briefcases for the WWE & World Heavyweight Championship contracts (2012)