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I always preferred Cody Rhodes out of the Legacy dudes, even back when all the dirt sheets were reporting that Ted DiBiase was going to challenge The Undertaker at WrestleMania and that sort of thing.
DiBiase got derailed when he was aligned with Maryse. The two never had any chemistry together and the gimmick that his father played just didn't work with him. Damien Sandow has got the essence of what a "Million Dollar Man" type heel should be with his intellectual challenges and such.
Many liked his babyface run, but I felt it was boring as hell. I don't think it was the performances (they were quite good), but it never really felt natural that this guy who always had a sour attitude and thought he was better than everyone because he was rich would suddenly start slapping fans' hands. It probably made slightly more sense than Alberto Del Rio's face turn, given that DiBiase could explain that he had come to love the people and that money wasn't everything in life. DiBiase could have gained perspective and "matured" as an adult after having his career spiral whilst aligned with Maryse and focused more on the dollars than his abilities. But there wasn't much there to work with.
When DiBiase returns, I think they need to plug him in somewhere meaningful. His random little returns on Superstars where he wins a match and celebrates like he is going somewhere is not going to demand any attention from people. DiBiase needs a "re-branding," much like the one Curtis Axel has.
DiBiase should change his theme music, too. The "I Come from Money" song made sense when he was a heel rubbing it in everyone's face, but now that he's not doing that anymore, DiBiase could really use something a bit heavier. Given that he does have money, maybe the WWE should spring for him to have his favourite song or dream theme and use DiBiase's kayfabe personal wealth to explain why he can have this big song as his entrance theme?
Another idea is to look at the success of Bruce Wayne as a character in The Dark Knight Trilogy (and Batman in general) and Tony Stark in Iron Man. Those characters manage to be wealthy but somehow likeable and, ultimately, babyfaces in their stories. If DiBiase channelled the "millionaire playboy" type, he could get quite over and has a niche that no one else holds in WWE. The WWE should show vignettes of DiBiase hanging out at penthouses with beautiful women and cheekily talking about how great it is to be Ted DiBiase. Make the vignettes tongue-in-cheek, so that we know we are meant to like this guy and not hate him for getting into a hot-tub with beautiful Swedish women he doesn't understand.
For a first feud, why not have DiBiase set his sights on the Intercontinental Championship. DiBiase can respectfully talk about the heritage of the championship and just what it would mean if he could win it. Curtis Axel and DiBiase could play up a past together, and Paul Heyman could perhaps even try and woo DiBiase over as a client. The pops DiBiase could get for essentially telling Heyman to go screw himself could be enough to make people want to get behind DiBiase out the gate. DiBiase's reasoning for turning down Heyman could be his original character motivation -- he doesn't want anyone else's legacy; he wants his own legacy. Even if the WWE doesn't go through with the high-cost theme song for DiBiase, they could just bring back the Legacy theme and have establishing himself be DiBiase's true goal.
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