The Big Boss Man was a prominent upper midcarder for the WWE throughout the late 80s and early 90s, with him playing his role perfectly wherever he was needed, whether it be to push towards the main event or compete in the midcard. He moved very well for someone of his size, especially since he had to wrestle in full officer attire. His character was very 'gimmicky', but it fit in perfectly to the way professional wrestling was at the time, with it being full of bold gimmicks. He would leave WWE in 1993, before making several small returns from 1998 all the way until 2003. In the middle of that was a forgotten stint in 2001.
Boss Man's second run in WWE wasn't quite as glamorous as the first, with him now acting as a brute heel rather than a fun-loving cop. He would become an enforcer for Vince McMahon, later joining The Corporation, where he was very much a background character to the bigger stars. He would win some gold, with Tag Team and Hardcore Title reigns, but he was hardly at the forefront of many major angles aside from an abysmal Hell in a Cell match against The Undertaker at WrestleMania, and a failed main event push during a WWE Title feud with the Big Show, which flopped.
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Over the next year or so, he was relegated to losing TV matches, before going down the card further, only competing on Sunday Night Heat and on house shows. In April of 2001, he would stop competing and seemingly disappear from the company. The only time he would show up over the next few months was on an independent show, with his WWE career up in the air. However, he would once again return to the WWE late in December of 2001, in what might be one of his more forgettable returns.
On the December 20 episode of SmackDown in 2001, the show was built around the WWE trying to nail down a contract for Booker T to make him fully WWE property following the Invasion. There seemed to be something that Booker was overly happy about throughout the night, but it wasn't clear exactly what that was. The main event of the night would see Steve Austin battle Booker T in a First Blood match, with the pair going back and forth in a brawl to close the show.
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Towards the latter stages of the match, Big Boss Man would appear out of nowhere, no longer donning his old attire, but instead wearing a suit. He would clock Austin with a chair, making the Rattlesnake draw blood, leading to Booker picking up the victory. This had been the plan all along, it seemed, with Vince McMahon laughing as the show went off the air. The follow-up on Raw was simply that it seemed as though Boss Man was to act as Booker's enforcer, and that was that. There was no grand introduction despite an eight-month absence, with little being made out of his return.
The Rock, but they made little to no advancement as a duo. Less than a month after they had joined forces, their tandem was disbanded without any rhyme nor reason, with Boss Man steadily leaving his spot on TV once again to work on lesser shows like Heat, aside from a few unspectacular losses on Raw and SmackDown where he was presented as a glorified jobber, whilst Booker turned out to be a success on his own.
Things didn't improve for Boss Man as time went on, as he struggled big time to get any chance to make an impact, although he wasn't as young as he once was, so it may have been understandable. He did briefly team with an also aging Mr. Perfect, but that duo was short-lived too, with nothing ever really sticking for him in terms of direction and character.
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In May of 2002, Boss Man would go up against Tommy Dreamer in what would ultimately turn out to be his final WWE match per cagematch.net, where he went out in a losing effort, completing what was an absolutely pointless return to action. He didn't add anything to storylines, he was never the focus, and the legacy he had built up over the 80s and 90s was seemingly just ignored. Following a small stint as a trainer in OVW, Boss Man was released in 2003. This was a terrible return for Boss Man, and it would be unsurprising if fans had removed this from their memory, as it served no purpose whatsoever.