A lot of the guys who have made this list had their pushes snuffed out before they made it to the mountaintop, but in the case of Rob Van Dam, circumstances led to his downfall while he held the richest prize in the business. When he debuted in WWF/E in 2001, RVD almost instantly became one of the most popular wrestlers on the roster. However, it took several years before he would finally break through to the top of the card, cashing in his Money in the Bank briefcase and winning the WWE Championship from John Cena in June 2006. Van Dam would be christened the new ECW champion as the extreme branch re-launched, but his adventure as a dual champion would be short-lived. Just a few weeks later, RVD got busted for drug possession, and he would quickly lose both titles in back-to-back matches on Raw and ECW before being suspended for a month. Less than a year later, Van Dam left WWE and would not return outside a surprise Royal Rumble appearance for six years.