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Wonder if they could continue this storyline arch for him in a different direction, like maybe one of the legends (maybe one from the back, like a road agent or something) claims they see something in him and becomes his manager. (Could be Road Dogg, for example, with the whole musical background in his character)
We get him losing but getting in increasing amounts of offense for a number of weeks, all the while showing a few shorts promo bits on Raw or Smackdown of him training with Road Dogg (could be funny as well with Road Dogg involved). Then, finally, he gets a big win, followed by more wins and goes on a bit of a role. He starts to get cocky and they tease friction between him and the legend manager.
Eventually they could build to him turning on the legend manager and setting up a PPV match against them with him going over, setting him up as a good mid-card heel with a bit of a background, makes his character a bit more well rounded. Could easily challenge a face champion like Santino for the US title after a feud like that...
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