7. Ted DiBiase Jr.
The gimmick was tailor-made for him, for the most part. His father, "The Million Dollar Man" Ted DiBiase, played it beautifully in the 80s and 90s. He had more money than you did, and therefore, that made him better than you were. It's a really simple gimmick, but it was incredible effective. There were plenty of times when DiBiase was the WWF's top heel, getting bigger heel reactions than anyone else in wrestling. Again, the "Million Dollar Man" style of gimmick was tailor-made for Ted Jr. Everyone hates an arrogant prick of a millionaire, but what everyone hates more are the millionaire's entitled, arrogant prick children. The children that are now rich without having done anything to earn the money. The children that feel they're somebody special because their parents have worked hard for several decades. This had led to the "famous for no reason" generation we have today, with people like Paris Hilton and the Kardashians becoming famous simply because they are the offspring of people who have made money. It just never worked out for Ted Jr, though. He has nowhere near the same level of charisma that his father had (and still has to this day when he makes the occasional WWE appearance), and his in-ring work, while never considered "bad", was just incredibly boring, especially in comparison to a lot of the exciting action that the rest of the WWE roster was delivering. Ted Jr had basically lost from the moment he debuted.