During the Monday Night Wars, Shawn Michaels was one of the top stars of WWE, but WCW tried to sign him as they had tried for other talents in WWE. It seems there were a few reasons for this.
During 83 Weeks, Eric Bischoff was asked if he was ever interested in signing Shawn Michaels to WCW back in 1993. He explained that WCW did not possess the money to pay for a bigger star at that time. To add to that, Michaels had a reputation for being very difficult to work with.
“Shawn had a reputation for being difficult to work with. When you reach a certain level of success in the entertainment business, there is a tendency to become a primadonna. I think that was Shawn Michaels’ reputation. I don’t remember anybody even suggesting for a minute to bring Shawn in. I like Shawn Michaels and I have a ton of respect for him. I think Shawn would say that during this period of time that he was distracted with a lot of bad habits and probably wasn’t at the top of his game mentally or emotionally. You have to remember WCW in 1993 didn’t have a lot of cash laying around. There was nobody in 1993 in Turner Broadcasting, Ted Turner included, that was going to write any big checks. WCW was broke in 1993.”
HBK stayed with WWE till the end. We do wonder what would have happened had he signed with WCW at the time.