Shelton Benjamin’s singles push led him to a post-WrestleMania 22 program with Rob Van Dam, the second-ever holder of the Money in the Bank Briefcase. Benjamin, the Intercontinental Champion, appeared alongside Van Dam in the second-annual Money in the Bank Ladder Match, and began to agitate RVD in the weeks to follow with the intention of challenging him for his Money in the Bank briefcase. Van Dam agreed to Benjamin’s proposal, provided he put his Intercontinental Championship on the line first. Instead, Benjamin entered a match against a mystery opponent the following week on “Raw” with a big stipulation: If he won, RVD’s briefcase would be on the line at Backlash, while if he lost, his Intercontinental Championship would be on the line. The mystery opponent turned out to be Benjamin’s former tag team partner Charlie Haas, who beat him with a jackknife roll-up after Benjamin attempted to taunt RVD.
Desperate, Benjamin begged Mr. McMahon to make things right. As a result, Van Dam had the same stipulation imposed on him, though instead of a mystery opponent, he had to defeat The Spirit Squad in a five-on-one handicap match. With Van Dam falling victim to superior numbers, his impending match with Benjamin became winner-take-all, an epic first that saw the Intercontinental Championship and Money in the Bank Briefcase be put up for grabs in the same match. Van Dam ended up defeating Benjamin in just under 19 minutes of hard-hitting, hyper-athletic fare befitting of the skills and abilities of both wrestlers. The only downside to the month-long program between Van Dam and Benjamin is that it did not last longer, as the two made for natural adversaries between the ropes.