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WWE took a chance signing Scott Steiner in late 2002. He was the last WCW guy they brought in and was definitely not on their Priority List to bring back due to his backstage reputation, not too mention the troubles he had in his first WWF run.
WWE took a chance signing Curt Hennig & Scott Hall too with their drug issues. They also took a chance signing Hogan with his backstage rep (which is minor compared to the very bad reputations that Hall and Steiner carry) and Steve Austin with his injury prone issues.
Sometimes the gambles pay off (Hogan, Austin), sometimes they don't (Steiner, Hall). Like Hall, Steiner has only himself to blame for having a history of pissing away his career in various ways.
Going into his 2000s WWE run, Steiner was pushed hard when he came in but wrestled poorly and had a bad attitude when he wasn't main eventing after getting benched for Mania 19 in favor of Booker T. Considering how much trouble he caused in WCW, he's lucky he even got that chance.
