Meltzer recalls Pillman conveniently scheduling a surgery around a match that he didn’t want any part of. While working in WCW, Hulk Hogan wanted Pillman included in an upcoming match where he and Randy Savage were going to basically squash eight other competitors. Hogan wanted Pillman in the match because he was so over, and Hogan wanted to pin him last.
Pillman knew that this would be the absolute worst thing for his character at the time and wanted no part of it. He even told Meltzer at the time that this might be one of the worst matches of all time, and it turned out to be just that. Pillman scheduled surgery for himself so he wouldn’t have to take part in this match.
Meltzer informs that Pillman and Bischoff worked together to get him his release from WCW, but the plan was for him to always return to the company. In the meantime, Pillman began negotiating with WWE.
After signing with WWE Pillman began struggling with drug addiction and this resulted in him crashing several vehicles. One crash in particular nearly killed him, and it resulted in him requiring ankle fusion surgery. From that point on it was very difficult for Pillman to perform in the ring, and he struggled to simply walk through airports on his surgically repaired ankle. He soon dove further into drug abuse.