Despite all that, Tannenbaum’s piece shows that there are still traces of the old, rebellious Simmons within the Sports Mogul. For one thing, it’s quite clear he hasn’t completely embraced the ESPN culture. Consider this passage on his relationship with the Worldwide Leader:

Once Simmons got an ESPN assignment, he quickly found an audience. But just as immediately, his relationship with the Worldwide Leader in Sports was full of conflict. “ESPN was idiotic,” says Simmons, who can match any athlete for self-confidence. “They fucked with my column for the first year, taking out jokes, and I was pissed off. They were rebuilding their site around me, but they were paying me nothing. So I had a meltdown: I didn’t turn in a column. I was like, ‘Attica! Attica!’ ” He laughs. “I was probably smoking too much pot.”

ESPN rewarded his work strike with a raise. “Bill likes to be in control,” an insider says. “In the early days, he was very upset about where they placed his column, versus where other columnists were. He’s a great advocate for himself and his brand.”

It wasn’t Simmons’ last fight with his bosses. They’ve suspended him from Twitter twice for tweets: for referring to Boston sports-radio hosts who worked for an ESPN affiliate as “deceitful scumbags,” and also for saying an interview that aired on ESPN was “awful and embarrassing.” Does he think they were right to suspend him? “No, I don’t.”

ESPN is owned by the Walt Disney Company, and some of Simmons’ behavior — like, say, calling soccer “gay” or mocking people for being fat — makes him a far more troublesome employee than Mickey Mouse. Periodically, the two parties get annoyed at one another. ESPN president John Skipper once said working with Simmons was “about 99.8 percent great.” (“Working with ESPN is 99.1 percent great,” Simmons counters.) Convincing the network to do 30 For 30 required “a year of arm-twisting,” he says. When it was a success, and his basketball book had been a big hit, his contract was up for renewal. “I had a little leverage.” He told ESPN that he wanted his own site, or he’d leave and do it elsewhere.

That situation may be playing out again before too long. While the Sports Mogul and the Worldwide Leader may seem more joined than ever thanks to Grantland, 30 for 30, NBA Countdown and more, Simmons told Tannenbaum (in an additional quote published at Deadspin) that “My contract expires next year. If ESPN doesn’t have the broadcast rights to the NBA, it will make me re-evaulate what I should do next. I want to work for whoever has the NBA.” That probably doesn’t mean anything major; it’s very difficult to see ESPN winding up with no NBA games considering all they’ve invested in the sport, and Simmons is also likely trying to boost his own leverage here.

Still, for all the success the Sports Mogul has found building an empire at ESPN, there are still definitely parts of the rebellious Sports Guy within him that aren’t thrilled with its corporate hierarchy and culture. Simmons has certainly changed over the years, but it hasn’t been a complete transformation. Perhaps the Sports Guy and the Sports Mogul can co-exist after all.

About Andrew Bucholtz

Andrew Bucholtz has been covering sports media for Awful Announcing since 2012. He is also a staff writer for The Comeback. His previous work includes time at Yahoo! Sports Canada and Black Press.

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