Kevin Sullivan had a long career, he worked for many promotions and played many characters. His career has had quite a few strange turns inside and outside of the ring which could put him in the position of having the weirdest career of any wrestler ever.

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Kevin Sullivan As The Prince of Darkness

Sullivan was a territory journeyman and NWA mainstay for many years before he hit his stride in Championship Wrestling, a Florida-based territory, portraying the character of “The Prince of Darkness.” As this character, Sullivan was able to tap into society’s fear of Satanism, witchcraft, and the occult in a way which wrestling had never seen before. It helped that the 80s was the peak of this paranoia with the popular tabletop game Dungeons & Dragons causing quite a stir amongst some religious groups.

Kevin Sullivan was one of the few who was able to cash in on the trends of the time. Wrestling in the southern Bible belt region, Sullivan was able to antagonize a fairly religious audience with his Army of Darkness faction, which included “Superstar” Billy Graham, The Fallen Angel (Nancy Benoit), The Lock (Winona Littleheart), and Sir Oliver Humperdink. His faction would attack the psyche of his opponents, leaving audiences bewildered and uncomfortable.

In his article, When Wrestling Went Metal, Benjamin Welton says, "During their heyday, Sullivan’s cult came to the ring and a series of black-cloaked and corpse-painted minions who usually brought with them boa constrictors of varying colors and sizes. Add in a half-naked Fallen Angel (Nancy Benoit), and then you’ve got a good idea of just how much of a spectacle Sullivan’s Army of Darkness was.

If you watch any of Sullivan’s matches from 1982 until 1988, you can see them in the audience booing or threatening to beat the spirit of the Lord into Sullivan’s ungodly Yankee body. For the Army of Darkness, this was proof positive that the gimmick was working; for the audience, the Army of Darkness was proof positive that the world, or at least Florida, was going straight to hell. If you were a child in the ‘80s, it was something you didn’t want your parents to catch you watching!”

In a shoot interview with Kayfabe Memories, Sullivan admitted he even wanted the boys in the back to be convinced he was a real devil worshipper, thinking that if he could convince them, he will get even more over with audiences at the shows.

The success of the Army of Darkness lead to his career in WCW. Sullivan altered his character to become the Taskmaster, adapting to the less edgy, more family-friendly style of WCW at the time. Sullivan became the booker of WCW (and would remain as booker throughout the Monday Night Wars) and it was at this time when Sullivan formed the infamous Dungeon of Doom, a main event faction who were particularly memorable throughout their feud with Hulk Hogan. Hogan even showed the first signs of becoming a heel in this feud, as Sullivan seduced him to the dark side for a short time.

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In 1997, Sullivan lost a retirement match to Chris Benoit, though that is just the start of the story.

Chris Benoit's Relationship With Kevin Sullivan

In his last feud as a full-time wrestler, many say that Kevin Sullivan booked his own divorce. His real-life wife at the time was Nancy Toffoloni, who portrayed his valet, Woman. As booker of WCW at the time, Sullivan booked the storyline of Chris Benoit luring Woman away from the Dungeon of Doom. Since these were the days of kayfabe, Sullivan insisted that Chris and Nancy would travel together to shows and eat together in public to give off the illusion that the storyline was real.

Sure enough, the storyline did become real as Nancy would eventually divorce Sullivan and marry Chris Benoit in real life.

The repercussions of this feud would have real life consequences years later. After the tragedy in 2007, in which Chris Benoit murdered Nancy and their son Daniel, conspiracies theories started popping up online suggesting that it was Sullivan who had killed Chris, Nancy and Daniel and then framed Benoit for the whole thing.

Obviously, there was no evidence of this and it was confirmed Benoit committed murder/suicide. In an interview with Chris Van Vliet, Chris Benoit’s son David Benoit confirmed that police had investigated Kevin Sullivan and ruled him out of any wrongdoing. David would say, “Conspiracy theories are just a joke. Just a joke. Kevin Sullivan didn’t do anything. We looked into that. We had the police look into him.”

Kevin Sullivan definitely had a long and strange career but it can’t be denied he played a big part in the evolution of wrestling over the years.