14. Jack Swagger waits just two days to cash in briefcase and wins World Heavyweight Championship, 2010
I know you’re probably looking at me a little funny right now and I can understand why.
Yes, Jack Swagger was a former Money in the Bank winner and yes, Jack Swagger was a World Heavyweight Champion at one point seven years ago.
Believe it or not, plans were supposed to be much bigger for Swagger in the coming years after his MITB victory and his cash-in victory over then-World Heavyweight Champion Chris Jericho just two days after winning the briefcase at WrestleMania XXVI.
But, before we hit on that, let’s break down Jack Swagger becoming Mr. Money in the Bank. WrestleMania XXVI brought the biggest Money in the Bank ladder match in history with 10 different competitors, including Swagger obviously. Swagger won the briefcase and then the question became, when was his moment going to be?
After just two days (although it was five on television because SmackDown wasn’t always live or on the USA Network), Swagger cashed in after Edge got some retribution from losing to Jericho for the gold at WrestleMania. It was similar to the cash-in attempt from CM Punk (which is coming later on this list) and actually, almost happened on RAW when Swagger looked to cash in on John Cena after he beat Batista for the WWE Championship the night before.
Despite the cash-in attempt, Swagger was a rather underwhelming champion in his short period of holding the gold and blew his chances to become a big star later on after an out-of-the-ring incident with drugs before WrestleMania 29 in New Jersey a few years later.
Oh, what could’ve been for the next People’s Champion.