4. Ted DiBiasie Sr.
The Million Dollar Man was a great gimmick, conceived by Vince McMahon and given to Ted DiBiasie in 1987. With his gaudy suits and ostentatious "Million Dollar Belt" DiBiasie was a man you wanted to hate, and man you wanted to see get his comeuppance. He was the premier heel in the late eighties, culminating with his foiled plot to buy the WWE Championship from Andre the Giant. DiBiasie actually held very little singles gold during his tenure with the WWE, his biggest accomplishment arguably being his Tag Team Title reign with IRS as the Million Dollar Corporation or possibly his King of the Ring victory in '88. There was no surprise that in 2010 he was inducted into the WWE Hall of Fame. DiBiasie competed in 4 Rumbles between 1989 and 1993, lasting a total of 75 minutes over his 4 outings. In the 1990 Rumble DiBiasie started the match as No. 1 and lasted 44 minutes, an impressive feat of endurance and one that his son (Ted DiBiasie Jr.) replicated in 2009. He was also the runner-up in 1989 after purchasing the coveted final entry, no.30, and surviving through to the final two with the eventual winner Big John Studd. DiBiasie buying the Rumble win would have been another classic move from The Million Dollar Man, surpassing his need for physical excellence and relying upon his vast wealth once again. DiBiasie would have been a great Rumble winner: completely undeserving winner who, having bought his way to success, would still be rubbing that success in everyone's face. He'd be the Kim Kardashian of 1980's wrestling, completely underserving of success but somehow obscenely proud of it. We'd just have to hope he made different decisions regarding video releases. Which Royal Rumble could they have won? 1989. This would have been a good year for DiBiasie to win the Rumble. DiBiasie had already purchased the No. 30 entry, so it wouldn't have been a huge leap of the imagination for him to have also bought the compliance of some of his competitors. With no title shot available his win would have just been another feather in DiBiasie's cap, a huge confirmation of his already legendary heel status.