#4. Raven
The hardcore icon Raven was once thought to have a bright future with WWE, even though his wrestling days were dwindling.
Possessed of great creativity--he even penned novels and comic books--WWE made Raven a backstage writer, a role he performed quite well. However, spending all that time with officials backstage worked against him in an unusual way. He was fired and blacklisted from WWE because of his friendship with Shane McMahon.
Shane and Raven would go out drinking together and become heavily intoxicated. While drunk, Raven would complain about decisions Shane's father Vince made. The still-drunk Shane would call from his hotel room and ramble at his father about all the things Raven said he was doing wrong.
Vince eventually got tired of this cycle and fired Raven, shutting the door on any future returns. So unless Vince thaws his attitude or retires as CEO of WWE, Raven won't be working for them anytime soon.