6. Randy Orton (2013) 35 days
WWE.comThe most recent round of MITB ladder matches featured an all-stars match consisting of six former world champs (Orton, Punk, Bryan, Christian, Sheamus and RVD). Orton would emerge victorious and then carry his briefcase around on Raw, threatening to cash in on champ John Cena. Five weeks after winning it, Orton pulled off the most sinister cash-in to date. At SummerSlam, Daniel Bryan had the feel-good moment of the summer when he knocked off John Cena for the WWE Championship in an instant classic. Orton wandered out, briefcase in hand, only for guest referee Triple H to turn on Bryan, Pedigree him and allow Orton to cash in and capture the title in mere seconds, thus completely deflating the crowd. The cash-in kicked off a feud that saw the title vacant more than it was held by either man. http://www.youtube.com/watch?v=elNxWbmycrs Of course, we all know how this story ended, with Bryan overcoming the odds at WrestleMania XXX and finally defeating Orton (and Batista) once and for all to capture the WWE World Heavyweight Championship.