Jim Ross Regrets Fighting with Vince McMahon Over Wearing a Cowboy Hat

Jim Ross earned widespread recognition as a commentator with WWE. Despite his dedicated efforts and contributions, he never fully gained Vince McMahon’s favor. Recently, Ross reminisced about a time when he defied McMahon’s directive to wear a cowboy hat and how it ended up costing him.

Jim Ross spent several years with WWE, gaining deep insight into the company’s inner workings. His extensive experience working closely with Vince McMahon has not always been smooth; Ross has faced ridicule on multiple occasions as a result of their interactions.

While speaking on his Grilling JR podcast, Ross’ co-host Conrad Thompson talked about Jim Ross’ wife Jan asking him the circumstances of Vince McMahon firing him, reminding Ross that he said at the time it was because he was reluctant to wear a cowboy hat and play the character.

Jim Ross acknowledged that he may have been wrong about making a big deal over what was essentially just costume television apparel. He compared it to an actor questioning whether they need to grow a beard or wear a specific costume. Ross said he didn’t mind wearing the hat; he wasn’t overwhelmed by the simplification of his character’s attire, which included things like a string tie and a Porter Wagoner-style jacket with wagon wheels, horses, and cows.

Ross noted that such attire was outdated and no longer appropriate for television. Ross stated that he could handle wearing a black hat and looked forward to it. However, he recognized that his refusal to comply with Vince McMahon’s request was significant because most people don’t have the experience of telling McMahon no and “living to tell about it.” In retrospect, Ross admitted that he had no real issue with the costume and regretted his decision.

“Conrad, I think I was wrong. I made too big a deal out of it when it wasn’t just costume television apparel. That’s like an actor going to the director and saying, ‘Do I have to grow a beard? Do I have to wear the hat?’ I didn’t care; the hat was fine. I wasn’t overwhelmed by the oversimplification of what my character was supposed to be.“

“You know, a string tie, a Porter Wagoner jacket with wagon wheels, horses, and cows. I kept saying we don’t dress like that anymore. You know, Porter Wagoner isn’t on TV anymore; he got canceled. I said wearing a black hat, I can handle that and I look forward to it. But here’s the theory: I told him no, and most people don’t have the experience of telling Vince McMahon no and ‘living to tell about it.’ I didn’t live to tell about it, but honestly, after looking back at it, especially in today’s world, I had no issue with it at the end of the day. But I said no, and he doesn’t like to be told no.”

Jim Ross also claimed that Vince McMahon lacked patience with unsatisfactory situations. Regardless, Ross has gotten wiser with age and realized his mistakes and that is all that matters now.

What do you think of what Jim Ross had to say regarding this? Do you feel Jim Ross’ relationship with McMahon suffered as a result? Sound off in the comments section below!

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