#2 Ted DiBiase Jr.
Iron Mike DiBiase was a multi-time champion throughout the various territories that existed in the U.S. during the 1950s and 1960s. ‘The Million Dollar Man’ Ted DiBiase was one of Vince McMahon’s greatest creations and enjoyed a highly successful wrestling career wherever he went. Ted DiBiase Jr...didn’t.
DiBiase was pushed in a significant way from the very beginning. He was paired with Cody Rhodes and worked many high-profile segments with Randy Orton during his initial years, which was proof that WWE’s bookers had big things planned for him.
Unfortunately, DiBiase’s flaws were exposed when he began branching out on his own. He lacked the charisma his father possessed and wasn’t really the same kind of grappling technician his father was, either. Simply put, he couldn’t fill his famous father’s boots.
WWE did try even further to get him over by pairing him with Maryse and Virgil (yes, that Virgil), but nothing developed. Ultimately, DiBiase left WWE in 2013 and retired from the wrestling industry shortly thereafter.