Brian Pillman’s reputation for creating tension wherever he went has long been part of his legacy, and a recently resurfaced claim from his biography adds another layer to his complicated history. The story suggests that Pillman saw The Undertaker as a want to be tough guy and did not hold much respect for him during their time in the WWF. That idea, once discussed on The Jim Cornette Experience, led Jim Cornette to explore why Pillman may have held that view and how both men were presented in wrestling during the 1990s.

Cornette explained that the disagreement likely came from differing ideas about toughness and authority during that era. The Undertaker held a powerful position in the locker room, backed by his size, longevity, and influence within the Bone Street Krew. Pillman came into the WWF with a football background and a habit of stirring conflict to keep his character unpredictable, which often made him clash with established expectations.

Cornette noted that many early impressions of Pillman were shaped by his smaller frame and his high flying presentation as Flying Brian. He pointed out that some veterans did not immediately realise the genuine physical intensity Pillman brought to the ring. Cornette said, “I do not know whether he thought I want to be tough guy because The Undertaker is a tough guy, but so was Brian Pillman. And I can see that maybe Brian thought and maybe with validity, because a lot of guys, when they first saw Brian, they did not think much because he was short and he was not, you know that not only that big… and also the hair, the fluffy hair, and the whole thing when he was younger, and he was flying Brian.”

Cornette recalled that Pillman did not always receive a warm welcome in the locker room. One example came from 1997, when Pillman returned from a match to find his hair dryer with the large diffuser broken and stomped on. Cornette suggested this happened before many wrestlers fully understood Pillman’s story and could have deepened any resentment he held toward authority figures.

There was also the possibility of old tension. Pillman and Mark Calaway briefly crossed paths in WCW in 1990, and Cornette believed any lingering friction from that period might have carried into their WWF years.

By 1997, Pillman was dealing with far more than locker room politics. His 1996 car accident had left him in chronic pain, led to medication issues, and caused bouts of paranoia that affected how he interacted with others. Cornette said, “Brian’s relationships with most of the guys in the WWF at that point probably would not have been the best… if he was coming in as the old Brian who had not been injured, was not trying to hide stuff, was not paranoid about things, was not having personal issues.”

Shawn Michaels echoed this while recalling seeing Pillman shortly before his death in 1997. Michaels described Pillman as looking unwell that night, adding, “And remember, came out after his match got into his bag, and he had beer in his bag, right? throwing some stuff down, drinking a beer, and he looked bad.” Michaels said he was not close to Pillman but stressed how difficult it was to direct anyone in that environment, noting, “You cannot, you cannot tell anybody in this business what to do.”

Given Pillman’s mindset at the time, it is easy to see how he might have viewed The Undertaker’s leadership role as unwelcome scrutiny. To someone trying to hide pain, stress, and instability, a locker room enforcer could feel more like an obstacle than a support.

Cornette also took time to compare the Undertaker of the past with the public figure Mark Calaway is in 2025. Years of podcasts, interviews, and public commentary have made Calaway far more visible than the Dead Man ever was, and Cornette believes that shift has disappointed some fans. He said, “It all those years, The Undertaker was a cool gimmick, and you did not hear the real guy talk. But now that they hear Mark Callaway, he is not really a great stand up comedian, motivational speaker. He is very Trumpy.” Cornette even joked about his appearances with his wife, adding that the mystique fans once protected has faded. Brian Last agreed, saying the gimmick should have remained universally loved, while Cornette stressed that Taker should not be political.

That modern contrast places Pillman’s old comments in a different light. While Pillman questioned The Undertaker’s authenticity decades ago, debate over the blending of character and reality continues even today.

With Pillman no longer alive to share his full truth, the exact nature of his issues with The Undertaker remains unknown. What is clear is that the clash likely came from a combination of personality, presentation, authority, and the personal struggles that marked Pillman’s final years. His chaotic edge and anti authority mindset made him challenge almost anyone in his path, and The Undertaker’s firm leadership style likely made him a natural target.