5. Vince Russo
Vince Russo's stints in TNA did him no favours, carrying over much of the shenanigans he dabbled in while booking WCW into the ground. Speaking of booking WCW into the ground, the guy made himself the World Champion in 2000.
In a typically weird spot, Goldberg interfered in Russo's title Cage Match against Booker T, spearing the writer through the structure and out onto the floor... giving him the win by accident. He held the belt for a week before deciding he wasn't actually a wrestler and just giving it up.
These days the Long Island native has his own podcast which is its own unique form of entertainment, ranting until the cows come home on anything and everything about the industry. He's released two books as well, and has also found the time to kick off an incredible beef with Jim Cornette that has resulted in a restraining order and multiple attempts at setting up a legitimate fight between the two.