It was, he would later tell a confidant, like something out of The Godfather. Bill Simmons was meeting with two of the most powerful executives at ESPN, John Skipper and John Walsh, in a conference room in ESPN’s then-unfinished Los Angeles office hard by the Staples Center. Within three years, this would be the Grantland office and thus the seat of Simmons’s power, but on this day he was feeling vulnerable, having spent much of 2008 in a sulk over one thing or another, whipsawed between his own petulance and his company’s prudishness. He’d had a run-in with Skipper a few months earlier. The then-VP had gotten uncharacteristically tetchy with him over some intramural sniping at ESPN’s newest big-ticket hire, Rick Reilly. Would the Sports Guy even have his job when he left the conference room in Los Angeles?


Simmons decided to lay everything out on the table, according to a source. His big complaint was over his weekly ESPN.com column. His editor worked on West Coast time, and the column, filed on Thursday night, wouldn’t hit the web until Friday afternoon, squandering hours of potential traffic. As Simmons saw it, according to the source, Skipper and Walsh were taken aback; they’d had no idea, and the meeting ended with the two of them promising to set things right.

It brought a peaceful conclusion to what was Simmons’s most fractious year at the company, and it seemed to confirm two central truths about Bristol: that the Disney property had grown so unwieldy that it could engage in open conflict with one of its most valuable talents without the people running the shop having any idea why; and that John Skipper, who would become president of ESPN in 2012, could be counted on to see things from his star’s perspective.


Six years later—with Simmons again on the sidelines, having been suspended three weeks without pay for restating conventional wisdom about NFL commissioner Roger Goodell on his podcast in a mildly profane manner and daring his bosses to punish him for it—only one of those things could reasonably be said to be true.

In the ESPN oral history Those Guys Have All the Fun, Simmons describes a certain type of employee who has problems with ESPN: “Very impassioned almost to a fault, and we just can’t believe ESPN works this way, and why can’t it work better, and it’s just like we’re a bad match for a company like that, and I think that’s why a lot of those people have left.”

It’s easy to read this as Simmons describing himself, and equally easy to understand disbelief at the way ESPN works. All through 2008, in the months leading up to his meeting with Skipper and Walsh, Simmons was, from his perspective, faced with a nearly uninterrupted series of provocations and insults.


In spring of of that year, the network nixed Simmons’s scheduled podcast with then-presidential candidate Barack Obama, canceling it “at the last minute.” The official line was that ESPN didn’t do politics; Simmons strongly chafed at that and, privately, at apolitical references to current events being taken out of his columns. At the same time, Simmons was taking public shots from Rick Reilly, who disparaged his colleague as a “blogger” who needed “a Lincoln Continental, if not a Greyhound bus, full of editors.” Simmons complained to higher-ups that Reilly’s inferior work was getting ESPN’s top real estate, both online and on the back page of ESPN The Magazine.

Fed up, Simmons gave an interview to Deadspin in which he was surprisingly critical of ESPN:

I still love writing my column and only re-signed last year because I really did believe that we had hashed out all the behind the scenes bullshit and come to some sort of agreement on creative lines, media criticism rules, the promotion of the column and everything else on ESPN.com. Within a few months, all of those things changed and certain promises were not kept.


A week later, he published an old article on his personal site, introducing it as coming from a time when “my column was starting to resemble what it’s like now, only if nobody was killing five of the best jokes or making me re-write them so they weren’t as funny.”

Bristol allowed the jabs to pass. Then Simmons gave an interview on Boston radio, in which he mock-earnestly praised Rick Reilly and his heartwarming tales of the triumph of the human spirit. It was Simmons’s first public mention of Reilly after absorbing multiple shots, but it was the breaking point for John Skipper, who gave Simmons a dressing-down.


Simmons has never made any secret of his love for Skipper, who like John Walsh has long been the columnist’s rabbi and his champion in Bristol. He’d never seen Skipper angry before, and the confrontation surprised Simmons. Rather than quit or accept a suspension, which he’d believed was coming, Simmons proposed time off to work on his book and to clear the air.

This didn’t entirely work. When he returned in September, according to a source, Simmons felt the atmosphere was even more uptight. One of his weekly NFL columns simply never ran on ESPN.com, under circumstances that remain unclear. Simmons said he turned it on time; an ESPN statement called it an “editorial decision.”


Around this time, ESPN also forced him to kick porn actors out of his private fantasy basketball league. Finally, in November, Simmons again went public. (His understandable frustration over ESPN allowing Rick Reilly to interview Barack Obama couldn’t have helped.)

First, he made a reference to the porn-actor ban on his podcast—which ESPN promptly edited out of the show before it went online. Then, Simmons quit his podcast in a protest that would last until mid-December, the impetus for his meeting with Skipper and Walsh in Los Angeles.


Things would improve, but the basic terms of the conflict had been established, and they evidently remain in place to this day: The bigger Simmons gets, the more he sees his prerogatives as falling out of plumb with those of the growing Disney property that employs him. Sure, Simmons wasn’t and isn’t fighting for anything nobler than the right to make gay jokes on his podcast, and, sure, you can understand a little why ESPNers might roll their eyes whenever the company’s most overindulged employee starts flinging shit from his throne in Los Angeles. But that doesn’t change the nature of the conflict. Simmons became one of the most powerful actors in American media by saying what was on his mind, and the corporation that facilitated that rise now would prefer he not do so.

In February 2009, Simmons went on buddy Adam Carolla’s podcast and told some entirely harmless dirty jokes. That led to a mess that involved Carolla claiming ESPN had banned Simmons from appearing on the show again, Simmons denying the ban, and ESPN memory-holing part of a livechat in which Simmons’s denial was questioned.


In October 2009, Simmons appeared on an episode of Kenny Mayne’s web series Mayne Street. The gag was that Simmons’s regular-guy persona was a total fraud, covering his actual decadent lifestyle and preposterously garish mansion. In the original version of the spot, Simmons lounges by a pool with two bikini-clad women. As he gets up to leave, one of the women asks him if they should make out while he’s gone. Simmons says to her, “You read my mind,” and then tells her to fill up the mud pit.

At least one person in Bristol didn’t find the video very funny. A week before, ESPN had suspended Steve Phillips for having an affair with a 22-year-old production assistant that turned into a stalking situation, and someone, perhaps even an executive, thought the Mayne Street episode was inappropriate in light of that particular mess. In Simmons’s telling, according to a source, the matter went before a committee, with ESPN executives holding a vote on whether the lines were funny or offensive; Simmons was told the vote was nearly unanimous. The episode was quietly taken down, with an edited version, minus the faux-lesbianism and mud pit, soon being posted in its place.

Simmons has likened this “censorship by committee” to his short-lived Sports Guy web cartoon, a dozen episodes or so of which aired beginning in 2004. The script for one, dealing with steroids in baseball, featured Barry Bonds’s head swelling until he turned into a giant Godzilla-like monster, breathing fire and destroying a stadium. It had been written and animated, but someone within ESPN felt the Godzilla parody was racist. That part was cut out of the final piece.


There were more issues with the podcast, too. On an episode in the summer of 2009, Simmons made a comment that didn’t reach his bosses’ radar until months later. This time his nemesis was ESPN VP Norby Williamson. From Those Guys Have All the Fun:

I had made some sort of joke like, ‘Note to soccer: if you want people to think you’re a little less gay, don’t call exhibition games friendlies.’ And we joked about it and moved on. So this guy or this girl— I don’t know if it was a male or female—hears this and flips out and sends an e-mail to Norby that I gay-bashed on the podcast.


Simmons said the attention from Williamson led to stricter standards for the podcast after that.

[T]hey start cracking down. So I ask Super Dave Osborne. He finishes the podcast I do with him. He tells this joke about— it’s a little off-color. They take it out. Little do they know he told the same joke on Conan O’Brien four days before, and it stayed in. So I’m like, “Now you’re telling me I don’t have as much leeway as an 11:30 late-night show on NBC? I have less leeway than that for a podcast with a fucking disclaimer on it?


In October 2009, Simmons appeared on the radio with WEEI, which months earlier had become an ESPN radio affiliate. The interview didn’t go well—Simmons believed the hosts went after him because he had publicly praised competing station WBZ—and WEEI hosts continued to criticize him in the days and weeks afterward, going so far as to name him their “Fraud of the Week.”

On Nov. 10, WEEI announced that Simmons had backed out of a scheduled interview. (Simmons claimed ESPN.com editor-in-chief Rob King had told him not to go on.) So Simmons went on the air with WBZ instead, and tweeted:

Hey WEEI: You were wrong, I did a Boston interview today. With your competition. Rather give them ratings over deceitful scumbags like you.


“I kept waiting for ESPN Radio to handle its ‘partner’ and it didn’t,” Simmons said of the tweet. “I ended up handling things for myself, and poorly.”

Years later, in Those Guys Have All The Fun, Simmons went further:

To be honest , I knew the “deceitful scumbag” posting would cause a splash, and I did it intentionally. That’s the same reason I went on the rival radio show. My attitude was, You guys aren’t handling this. You have let this fester and it’s become a real issue in Boston with these guys killing me for two weeks. I have a thick skin, and I’m totally used to getting killed by people, but this is our alleged partner, and they have on their website that I’m the fraud of the week, and you guys have done nothing. I escalated things intentionally to make them look at it and have meetings about it and fucking waste their day. That made me happy.


What happened next isn’t exactly clear. Simmons’s version of events is that he was never officially told he was suspended from Twitter for his tweet bashing WEEI—only that Rob King had asked him to take two weeks off, and that he had agreed. But when Simmons’s absence was noted, King wrote a blog post confirming it and calling it a “suspension.” Privately, Simmons chafed at the notion that ESPN had any right to suspend him from Twitter, telling people he interpreted it as a final warning: don’t tweet or we’ll actually suspend you. Either way, the timing made Simmons furious. His Book of Basketball had just come out, and he viewed Twitter as a huge promotional tool he was being denied.

Money and the promise of autonomy smoothed things over, as they often do. In the spring of 2010, Simmons re-upped with ESPN with a multi-million dollar contract that also included an agreement to finance what would eventually become Grantland. When asked how he convinced ESPN to fund his site, Simmons explained, “I would have done it with somebody else.”


And things were very good between Simmons and ESPN for a long time. (Bill even eventually got his interview with Barack Obama.) In interviews with the authors of Those Guys Have All The Fun, he was critical of colleagues including Chris Berman, Mike Tirico, and Mike Greenberg, and he wasn’t called to the carpet for it—at least not publicly.


Occasionally, though, the old conflict surfaced. It was as if Simmons, increasingly well-entrenched as ESPN’s face—not just a columnist and podcaster, but an editor of Grantland, producer of the 30 For 30 series, broadcaster on NBA games, and, functionally, a member of management—periodically needed to remind the public that he wasn’t really of ESPN.

In March 2013, Richard Sherman ruthlessly mocked Skip Bayless on an especially inane episode of First Take. It was—well, as Simmons would tweet that night, “awful and embarrassing.” ESPN suspended Simmons from using Twitter for the rest of the week. In June of that year, Simmons worked the NBA Countdown desk at the Finals and made a joke about Dwyane Wade heading to Germany for blood-spinning treatments. A later airing of the show edited the joke out, leading Simmons to complain on Twitter and take a shot at Stephen A. Smith at the same time.


Then, before this past season, Michael Wilbon was hustled off Countdown in a sign of Simmons’s growing influence over the show, resulting in Magic Johnson leaving the network altogether. Even Simmons’s denial hinted at tensions within Bristol. He claimed in a Nixonian response to SI.com’s Richard Deitsch that the Deadspin story about the power war was fake and had been planted by somebody at ESPN to make him look bad, neither of which was true.


All of this is the context for what finally came this week—Simmons’s three-week, unpaid suspension from all ESPN platforms, plus Twitter, for his podcast comments accusing Roger Goodell of lying and, especially, for daring ESPN to punish him.

What Simmons said was, in itself, harmless. Roger Goodell is a liar, as more or less everyone in sports media had said long before Simmons took to his podcast to wonder why no one was saying it. Simmons being Simmons, his “it’s such fucking bullshit” was presented in the spirit of bold truth-telling. Daring ESPN to suspend him came off as an adolescent tantrum, if not a non sequitur. Bristol being Bristol, it wasn’t taken that way.


As SportsBusiness Daily’s John Ourand and ESPN ombudsman Robert Lipsyte have reported, Simmons’s dare was, comically, taken as a legitimate challenge to corporate authority. This—along with, presumably, his history of mild insubordination—is what earned him a three-week suspension, out of all proportion to what other ESPN offenders have gotten.

More than that, though, the significance of the suspension lies in where it comes from. Both Ourand and Lipsyte, along with SI.com’s Deitsch, trace it directly to John Skipper. In all these stories, Walsh’s name is nowhere to be found. He apparently wasn’t involved.


Simmons has always divided the ESPN suits into the good cops and the bad cops. The latter has included the likes of former ESPN president George Bodenheimer (he said in Those Guys:”[T]hey’re willing to look the other way unless it ends up in the SportsBusiness Journal—if it gets in there, they know George is going to see it”) and Norby Williamson (whom Simmons has likened in private to The Godfather’s traitor, Salvatore Tessio).

In Simmons’s reading, John Walsh and especially John Skipper have always been in his corner. In nearly every previous clash with ESPN, Skipper has played the benevolent father figure, protecting him from the petty tyrants elsewhere in the company and giving him implicit free rein to keep doing what he does.


“Skipper has been my boss,” Simmons said in Those Guys, “and really, anything I’ve wanted to—other than interview Obama for the podcast—I’ve been able to do. They’ve never stood in my way, they’ve always tried to make things happen, and they’re always asking how to figure out how to do what I do under some of the constraints that we have.”

That isn’t the case now. Skipper isn’t merely yielding to a corporate culture that sees Simmons as the beneficiary of an unfair double standard. According to Lipsyte, he sees the situation as involving a question of character: “Simmons, Skipper believes, is transitioning into an important influence and mentor at Grantland, and needs to leave his well-worn punkishness behind.” While Simmons may be contemptuous of ESPN discipline, he’s unlikely to dismiss it as mere pettifoggery from ESPN tightasses when it comes from the executive he trusts the most, without any intervention from his other rabbi, John Walsh. And this isn’t happening in a vacuum: Simmons’s contract is up next year.


Would he actually consider leaving?

“I don’t know if the company is designed for people like me,” Simmons said around the time he signed his last contract, “but we’ll figure something out. It’d be a whole lot easier for me if I didn’t love Skipper and Walsh. If that dynamic was removed, it would be cut-and-dried, and I would leave.”


Dave McKenna, Tim Marchman, and Tommy Craggs contributed to this report. Top image by Jim Cooke.