Up to the Task: Remembering ‘The Taskmaster’ Kevin Sullivan

July 9, 2025

Posted on  by bdamage1

Brian Damage

He was a wrestler, a manager and a booker who had a great influence on the pro wrestling business for decades. Today on the blog, we look at the life and career of the man known as ‘The Taskmaster’ Kevin Sullivan.

Kevin Sullivan was a good amateur wrestler from Boston, who decided to give professional wrestling a try in late 1969, early 1970. Sullivan had no formal training and learned “on the job.” He first wrestled under the name Johnny West and then eventually Kevin Caldwell and ultimately under his real name. Sullivan competed for various territories including Montreal, Georgia Championship Wrestling, Memphis, the WWWF, Mississippi and Championship Wrestling from Florida. He credited much of his learning of the ins and outs of the wrestling business under the tutelage of Ole Anderson, Dusty Rhodes and Eddie Graham.

Sullivan considered Graham to be like a surrogate father to him and that is where he learned the most and had the biggest moments of his career while wrestling in the Florida territory. For a brief time, Sullivan got into bodybuilding, competing in a few competitions, thanks to his friendship with Tony Atlas. Sullivan’s career really didn’t take off until the early 1980’s. By chance, Sullivan was seeing on the news how the government was concerned with heavy metal music and the satanic influence it had on its young children. The so called “Satanic-Panic” was alive and well in the United States, espcially in the bible belt portions of the country.

Sullivan decided to create a gimmick for himself that made him into a satanic like cult leader. He started out by hanging in dressing rooms before and after shows blaring music like Ozzy Ozbourne and other heavy metal bands, all while acting like he was in some sort of a trance from their music. Kevin’s rationale for doing this, was to first make the boys in the back believe you are the Prince of Darkness and then that will assure you that the fans will buy it too. Indeed they did.

Sullivan formed a faction he dubbed ‘The Army of Darkness’ that saw him align with others like Mark Lewin, Curtis Iaukea, Luna Vachon, Bob Roop and Fallen Angel. According to Sullivan, fans down in Florida genuinely hated and feared his gimmick. Sullivan was allowed to push the envelope on the character and said the only time he felt he pushed too hard was when he was hung over the top rope by Dusty Rhodes. He felt that it was a bit too dark for families watching on TV. It was in Florida, where Sullivan learned the art of booking from Eddie Graham, who he said taught him the stark difference between great matches and drawing money.

Sullivan would join Jim Crockett Promotions courtesy of his friend Dusty Rhodes. Rhodes wanted Sullivan to bring his Army of Darkness act to JCP with the feeling that it would do big business with national exposure. The problem was, Jim Crockett Jr was a devout Baptist and decided that the entire gimmick was too dark for his liking. So instead, Sullivan was put in a faction called ‘The Varsity Club.’ A group that consisted of All American athletes being led by Sullivan. Kevin was not a big fan of the gimmick calling the members and himself “The Three Stooges.” He said Rick Steiner was Curly, Mike Rotundo was Larry, Sullivan was Moe, and “Dr. Death” Steve Williams was Curly Joe. Despite not liking the Varsity Club, he did admit that it generated good heel heat and made a babyface star out of Steiner.

Eventually, Sullivan became booker in WCW and created the ‘Dungeon of Doom’ faction, which he said was intentionally made cartoonish to help get Hulk Hogan over as a babyface in the company. He figured the more outlandish the gimmick, there was no way that fans would think they were cool heels and cheer for them. They would root for Hogan to destroy the DOD and end them. While the Dungeon of Doom proved ridiculous and too out of the box, Sullivan still had a great wrestling mind and booked many great storylines, such as the classic feud between Ric Flair and Ricky Steamboat and booked many of the early nWo angles.

Sullivan did admit that Vince McMahon came calling to join the WWF and were in serious negotiations, but Sullivan asked for too much money and Vince decided to back off. Sullivan was not a big fan of the WCW tag team of Hollywood Blondes (Brian Pillman and Steve Austin) feeling they were too good as heels to be a team, as they canceled each other out. Sullivan pushed for both Austin and Pillman to be single stars and saw big money in them both. Of course, I would be remiss if I did not mention his booking of his wife Nancy being paired with Chris Benoit. For years after fans and wrestlers said that Sullivan “booked his own divorce.”

The Taskmaster Kevin Sullivan is credited with giving Paul Heyman his first big break in pro wrestling, by making him a heel manager. He and Heyman formed a friendship and mutual respect for each other that survived the period where Sullivan was working for WCW and taking talent away from ECW. Sullivan said he would always give Heyman advanced notice before signing talent away, so he could properly book and prepare. Sullivan wanted to sign Taz and Tommy Dreamer, but said that Heyman relied heavily on both as stars and Sullivan did not want to go that far.

One Man Gang remembered his time wrestling in Florida and Eddie Graham was about to fire him because Graham felt he wasn’t much of a wrestler. OMG said that Sullivan stood up for him saying One Man Gang isn’t supposed to be a wrestler, he is a gimmick that sells itself. Graham relented and Gang kept his job in the territory. That’s the type of persn Kevin Sullivan seemed to be. He would attend wrestling conventions and sit in the hotel lobby with fans talking wrestling and sports in general.

Sadly, Kevin Sullivan suffered an accident and he apparently developed sepsis, which caused his health to deteriorate rapidly. He died on August 9th, 2024. He was 74 years old.

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