4. Edge Missing Out On The MITB At WrestleMania 23
https://www.youtube.com/watch?v=n7FmUijrySs If there's one wrestler who encapsulates what Money In The Bank is all about, it's Edge. Although the "cash-in" has gotten progressively tedious as the years have gone by, when Edge cashed in on a battered John Cena it was a revelation. He told audiences that "none of you saw this coming", and we didn't. Edge's second cash in felt contrived in comparison. Wait, second cash in? Despite not winning Money In The Bank at Wrestlemania 23, Edge ended up being the man with the briefcase once again after wrestling it away from career-long underachiever Mr Kennedy. So what we're left with is a fun ladder match, that ultimately stands as a reminder of Mr Kennedy's failed attempts at becoming a main eventer. But that's a mere irritation, something that in hindsight would have been changed if the following year could be predicted. Still, nothing to get too worked up about. After all, Edge ended up with the briefcase anyway. So why is it on this list? Because Edge had never lost at Wrestlemania. If booked to win MITB twice, Edge would have walked into his classic World Heavyweight Title match against the Undertaker 6-0. As great as that match is, imagine the intensity of a Streak vs Streak showdown to close the show at the Citrus Bowl. The creative issue with the streak has always been to find a way to make the audience believe that The Undertaker could lose. They did a great job building up Orton as a credible threat with his "Legend killer" moniker, but otherwise the outcome has always been tediously predictable. But while audiences know that the WWE would never end the streak, the possibility of them passing it on seems distinctly more plausible. Imagine the tension in the room when Edge cuts Taker in half with a spear, knowing he could not just end the streak, but make it his own.