Michael Wilbon Credit: Pardon the Interruption

While he was in Miami covering the NBA Finals, Michael Wilbon stopped by to reconnect with his former ESPN colleague Dan Le Batard. That led to Wilbon detailing his life and career on an all-encompassing episode of South Beach Sessions.

The whole conversation is worth listening to, but one of the highlights of the 75-minute interview was the revelation that Wilbon once nearly took a job as a columnist at his hometown paper, the Chicago Tribune. After much deliberation, including a conversation with Chicago Bulls legend Michael Jordan, Wilbon decided to stay at the Washington Post, where he wrote from 1980 to 2010. Once Wilbon turned them down, the Tribune quickly pivoted to another up-and-coming journalist, one by the name of Skip Bayless.

“The Chicago Tribune was saying come home. Skip Bayless took the space after I was offered [it],” said Wilbon. “They offered me the world. My hometown paper. The paper I delivered as a kid growing up. My face was already on the side of busses. They had the ad drawn up. I saw it.”

The decision, which he regards as arguably the toughest of his career, ate at Wilbon for weeks. And that prompted him to seek Jordan’s advice.

“We talked about it and I learned how much I didn’t know about money. The Tribune’s offer or the Washington Post, Don Graham’s offer. I literally went through it with Michael. And he had serious, hard advice. Like financial philosophy,” said Wilbon of his bidding war, which happened to coincide with Jordan’s “Last Dance.” “Guys like him—Charles [Barkley] and I were working on a book—they know so much more, even though those guys are four years younger than me, they know so much more about money and finance than we’d ever know as sports writers.”

While Wilbon insists he has “no regrets,” accepting the difficulties that come with being a journalist, he does acknowledge what his career cost him, missing out on precious moments he could have shared with his son, Matthew.

“He was seven before I spent Christmas Day with him. I spent Christmas Day with Magic [Johnson], Stuart Scott, Jon Barry, Jalen [Rose] and Stephen A. [Smith],” said Wilbon, now in his 23rd year hosting Pardon The Interruption. “He was in eighth grade and I went to a game and they said, ‘Did you hear what Matthew did Wednesday? Too bad you didn’t come to Wednesday’s game.’ I said, ‘What did he do Wednesday?’ ‘He had seven straight threes.’ I’m like, ‘What?!’ Yeah, I missed that. I miss a lot.”

By maintaining his loyalty to the Washington Post, did Wilbon indirectly provide a larger platform for Bayless (then a columnist for the Dallas Morning News), a career breakthrough that would open the floodgates to future success at ESPN and eventually Fox Sports? Who knows, though it’s a fun hypothetical to ponder, leaving us to imagine an alternate reality with Wilbon in Chicago and Bayless remaining a local fixture on the Dallas news circuit.

[South Beach Sessions]

About Jesse Pantuosco

Jesse Pantuosco joined Awful Announcing as a contributing writer in May 2023. He’s also written for Audacy and NBC Sports. A graduate of Syracuse’s S.I. Newhouse School of Public Communications with a master’s degree in creative writing from Fairfield University, Pantuosco has won three Fantasy Sports Writers Association Awards. He lives in West Hartford, Connecticut and never misses a Red Sox, Celtics or Patriots game.