I'd turn him heel and make the pimp gimmick gritty instead of funny.
He'd be a valet, not a wrestler, and he'd be a monster heel valet for a face diva thats a midcarder.
Beating up her female opponents and getting her ahead. Might even have some of the jobber girls he beats up join his stable against their will.
Give the face diva a push so that she is now facing (but losing to) top-level female superstars, but imply he beats her behind the scenes whenever she loses (increasing her babyface fans that feel bad for her and increasing his heat to X-Pac levels)
Then, I'd let him interfere in her eventual title match to win her the diva belt, but after that... he'd never let her hold it.
He would always carry it and talk about it like "Our championship or My championship" lke it was his and she'd look sad and co-sign what he said, increasing her face status as fans root for her to get away from him, and his heel status as ppl can't stand him.
Finally, I'd have a Cena or the Rock type of champion start feuding with him and using his pimp sweettalking skills on the mic Godfather would explain that he is already a champion, so the only way it would make sense is a title vs title match.