10 WWE Legends Who Should Have Won The Royal Rumble But Never Did

6. Ted DiBiase Sr.

Everybody has a price, according to the Million Dollar Man. He certainly proved that the Rumble has a price, buying the coveted number thirty spot in 1989. DiBiase finished as runner up that year and he has a couple of other good Rumble showings to his name. Ever the workhouse, Ted lasted 44 minutes as the No.1 entry in 1990. This was a nice bit of continuity from WWE after DiBiase's shameless purchasing of the thirty spot the previous year. The Hall of Famer was never the top heel in the company, although he did main event WrestleMania IV against a babyface Randy Savage so it might not have made sense for him to win the WrestleMania title shot. In 1989 the title shot was not on the line though, and that would have been the perfect time for DiBiase to win the Rumble. He would have been a more worth winner than Big John Studd, no doubt. Hell, he already bought the No.30 spot, so why not go a little further and have him pay off a bunch of cowardly heels to eliminate themselves?