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Not many NBA pros enjoy the loudest talking heads in the media. Especially the guys at All the Smoke. Setting their beef with multiple sports media personalities aside, they had Fox Sports’ former star, Skip Bayless on the podcast. Bayless had a lot of revelations from an extensive sportscasting career. Including the one NBA legend that didn’t take offense to his brash ways. Michael Jordan could truly turn anything into fuel and Bayless struck the right nerve. That’s more than what can be said for other NBA stars dealing with Skip Bayless.

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Bayless has been in every incarnation of professional sports media since 1974 when he graduated from Vanderbilt. Matt Barnes and Stephen Jackson wanted to know which was his favorite team to cover in a five-decade-long career. “’98 Bulls,” a very easy answer for Skip.

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Michael Jordan’s ‘Last Dance’ with the Chicago Bulls and the end of the dynasty was meaningful to many people, including Bayless. But Bayless had little contribution to pushing MJ towards the sixth chip. “Michael liked me and he didn’t like many in the media,” Bayless says which is true. Nothing personal exactly, MJ was notoriously media-shy. So it even baffled Bayless. “ I think he liked me because I was my own guy… and I didn’t care what anybody thought.”

In 1998, Bayless left a two-decade career in Dallas behind to become a columnist for the Chicago Tribune. Right away, he was making his way into the Windy City sports scene. Even Stak admits that Bayless is a “straight shooter.” Which cements why his ways appealed to Jordan’s hunt for motivation. “He got a kick out of me and he opened to me and would call me, if I left him a message, he would call me back.”

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A good few athletes would probably leave Skip Bayless on read. But not Michael Jordan. And now you know why Bayless is the Black Cat’s staunchest advocate. LeBron James probably doesn’t have the same policy as Jordan.

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Skip Bayless’ balancing act with Michael Jordan and LeBron James

It’s no secret that Bayless is the loudest LeBron James hater. More often than not, he uses MJ as a talking point to criticize James. For the most of it, Bron has made it a point to not acknowledge Bayless and his commentary at all. Although he has moments where he praises James.

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Someone decided to make a mockery out of it after Bayless’s unexpected exit from Undisputed. While sports fans speculate about his possible return to ESPN, a hacker took over the analyst’s X page to post fake tweets, including a fake apology to Bron. Bayless was able to get his account back and deleted all the false posts.

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Past that hiccup. Bayless is back on his Air Jordan bandwagon for good reason. His coverage of the ’98 Bulls was arguably the highlight of his long career. Within the first year in Chicago media, his column picked up awards. He can also narrate multiple stories that The Last Dance docuseries never touched upon in that era.  That’s the privilege of someone who has Michael Jordan on speed dial.

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Caroline John

3,534 Articles

Caroline John is a senior NBA writer at EssentiallySports, specializing in league comparables. She holds a master’s degree in Journalism and Communication and brings eight years of experience to the sports desk. Caroline made a mark in NBA media by covering the life of Shaquille O’Neal, which led to an exclusive interview with Josh Halpern, CEO of Shaq’s Big Chicken franchise. Her coverage was also personally highlighted by Shaq, who shared her article about his DJ Diesel persona and rapper GAWNE on Instagram. Drawn to the philanthropic work of LeBron James and Shaquille O’Neal, Caroline started following the NBA for its character both on and off the court, and has since become a respected voice covering many of the league’s biggest names. Her reporting stands out for accuracy, recognition from industry figures, and a strong connection with readers. Away from sports, Caroline is an avid reader, finding equal passion in books and storytelling.

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