9. Bobby Heenan
When Bobby Heenan took the money and left WWE for WCW, his career was never quite the same. While in WWE, he had an undeniable dynamic with his fellow announcers that wasn't even close to what he accomplished in WCW. While his work with Eric Bischoff, Tony Schivanoe, Mike Tenay and others wasn't bad, he definitely didn't seem as genuinely motivated as he was previously. He was one of the most hated heel managers and announcers of all in time WWE. But in WCW, he became an afterthought. WCW missed many opportunities to get Bobby Heenan involved in some top storylines. Imagine if he became Hulk Hogan's manager in the nWo after years of trying to destroy Hulkamania? This isn't a knock on Bobby Heenan, but when listening to his commentary in WCW, you could tell how uninterested he was in certain aspects of the show. If he would have stayed in WWE throughout the rest of the New Generation Era and into The Attitude Era, his talents would have no doubt been utilized to their full potential.