#4.) Dean Ambrose – 2016
It could be argued that Dean Ambrose’s MITB cash-in was the most satisfying one in WWE history. The reason for this is due to two simple words – poetic justice. A year prior, Ambrose failed in his attempt to capture the WWE World Championship from Seth Rollins, after The Architect won by sheer fluke in their intense ladder match.
Ambrose cut a heartfelt promo about not winning because of a “technicality”, expressing his frustrations but still vowing to become World Champion one day. On June 2016, in arguably the greatest MITB PPV of all time, Ambrose won the briefcase in one of the most star-studded ladder match line-ups ever.
In the main event, Seth Rollins defeated Roman Reigns to become WWE World Champion again. Just 2 minutes after, Dean Ambrose’s music hit. The Lunatic Fringe waited less than an hour to cash in his briefcase, ending the night by winning his sole World Championship in WWE.
It was one of the most perfect PPV endings ever, with all three Shield members having held the World title at one point that night.
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