“Use your best judgment at all times.”

—Jed Drake

That’s how a high-ranking ESPN executive hilariously described the company’s approach to commentary guidelines in 2008, well before tweeting mushroomed into ESPN’s third-biggest ongoing adversary (trailing only cord-cutters and common sense). Over the course of three astonishingly lucrative decades, ESPN built a juggernaut that feasted on live sports rights, highlights, radio content, print and digital content, journalism, breaking news and provocative opinions. The Worldwide Leader never really needed those opinions. For those first few years in Bristol, it never had them.

Eventually, ESPN realized something: If you aren’t commenting with style and substance, what are you? Would you rather be a drive-thru joint or an actual restaurant? ESPN decided to be both. That paved the way for Keith Olbermann and Dan Patrick, Mike Wilbon and Tony Kornheiser, Craig Kilborn and Stuart Scott, Chris Berman 2.0, The Sports Reporters, Outside the Lines, Sports Night, Cold Pizza, Around the Horn, ESPN.com, ESPN The Magazine, Page 2, and eventually, me and Jemele Hill.

They hired me in 2001 and Jemele in 2006, mainly because they didn’t have anyone like us. I made my mark as a wisecracking, sitting-on-his-sofa sports fan from Boston, while Jemele became the company’s black female sports nut from Detroit. My favorite thing about ESPN: You could start there doing one job, and within 10 years you might be doing four other things. It was the place where you pitched Grantland, 30 for 30, a 700-page NBA book or even a crappy animated cartoon … and the company might actually do it. Or you might stumble into your own daily show only because someone noticed that you and Michael Smith made each other laugh. It’s a company without a ceiling.

The worst thing about being a creative for ESPN? The company’s finest ombudsman ever, Le Anne Schreiber, spelled it out perfectly in 2008.

“Even longtime pros of the soundest judgment would be challenged by the compartmentalization of qualities ESPN asks of its on-air and online talent: be objective in the booth, subjective outside it; stick to the facts as a reporter on ESPN.com, but speculate beyond the facts when we ask for your analysis on TV; be edgy in your Page 2 columns, but don't cross any lines. Where are the lines? We'll tell you when you've crossed one.”

I don’t remember the first time I read that paragraph, just that I reacted like the groundskeeper in Rudy.

Le Anne never could have imagined what was coming. Over the next few months, as the majority of ESPN’s talent gravitated to Twitter (including me), that aforementioned “compartmentalization” became cloudier. Doesn’t everyone battle “bad judgment” on Twitter? Isn’t that kind of the point? You have a thought and throw it out there, and maybe one out of every 40 times, you wish you hadn’t. Live television or radio brings inherent caution; you measure your words because of the adrenaline. Twitter should work that way, too, but it’s too comfortable. Your fingers start moving, you stop giving a shit for three seconds, and suddenly … boom. It’s out there.

I knew that I would screw up on Twitter, eventually, but it never stopped me from tweeting.

In November 2009, ESPN suspended me for two Twitter weeks after I skewered the drive-time hacks from a Boston radio show. (I deserved it. Although so did they.) Three years later, I still had the same column and podcast, but I was also running Grantland, shepherding 30 for 30 (Vol. 2) and cohosting NBA Countdown. I had the highest concentration of ESPN Kool-Aid running through my veins in 2012. I believed in ESPN president John Skipper and worked my butt off for him. I wanted us to beat everyone else. I wanted us to be great. I really did. I took it personally whenever anyone at ESPN undermined all the terrific stuff we were doing, like the time First Take promoted a Richard Sherman–Skip Bayless showdown like it was a SummerSlam match.

If Schreiber was confused by ESPN’s objectivity-subjectivity issues in 2008, then this particular First Take episode probably split her cerebrum. Should we invite a famous NFL player to eviscerate our host in deeply personal ways? Apparently so! I couldn’t believe the clip, but I also couldn’t believe anyone was surprised by it. Wasn’t that the underlying point of this show: shoot from the hip, say crazy shit, try to back it up the best you can, and be ready to get called out at any time? Hadn’t they been courting a Sherman-Bayless moment for years?

I hopped on Twitter that night and typed this …

A few minutes passed. I realized people might think I wasn’t appropriately horrified by that train wreck of an episode. I typed this …

And this …

Within 36 hours, ESPN had suspended me from Twitter. My boss called and explained that—even though I was right—my profile had risen inside and outside the company. I had ignored one of their few crystal-clear guidelines: don’t attack other shows on ESPN. They couldn’t let it go.

My counter: They paid me and dozens of others to give my educated opinions on sports (and other stuff, too). The consistency and creativity of those opinions builds a certain level of trust with your audience. You have to be genuine. If not, people will see through you. Anyone who reached a certain level at ESPN fussed over being watered down, impeded or being made to seem less genuine. As I told Schreiber in 2008, “When you are supposed to push the envelope, but you are afraid of the repercussions of every decision, I think it affects you.”

It’s a constant give and take. I tweeted about First Take because, as someone who was working crazy hours for the company at the time, I felt personally betrayed.

What the hell was that? Is that where we’re going as a company? That’s what we are? Why am I killing myself every week for you guys?

And granted, that segment happened just two days after Grantland produced House Eats 3—our New Orleans eating contest that ended with Cousin Sal vomiting like the star of an Exorcist remake. But our silliest stuff was just that: silly. We weren’t demeaning the company. I never regretted those three tweets.

Sixteen months later, when my friend Michelle Beadle ripped Stephen A. Smith after his clumsy attempt to discuss the Ray Rice scandal, the company decided against disciplining her. Why? Nuance. Smith discussed domestic violence in an offensive way; she’s a woman; she was offended; she tweeted about it. Had they suspended Beadle for those tweets, it would have been ESPN’s dumbest decision in nearly 40 years. (Other than ESPN the Phone.) She backed the company into a corner. The powers that be could handle their decision only like … thoughtful human beings? What a concept.

If it seems like ESPN handles everything on a case-by-case basis, that’s because it does. It’s almost like a golfer wetting his finger, holding it up and checking the wind. Which way is it blowing today? That happens for five reasons: ESPN is way too big; ESPN draws way too much attention; ESPN has contradicted itself way too many times; ESPN’s business relationships can sometimes be in direct conflict with its obligation to report and entertain; and finally, ESPN is just TERRIBLE at this. It’s really, really bad. We have decades of evidence now.

BUT …

(And this is a big BUT …)

The bosses were always adamant about ESPN sticking to sports. They wanted ESPN to be your escape from the real world. We don’t care what you believe, how you voted or where you live. We won’t judge you. You’re safe here. Come talk sports with us. For writers and talkers and talking heads at ESPN, politics was our invisible third rail. There was no nuance. They wanted as many sports fans to consume ESPN as possible. Even when they bought FiveThirtyEight, they made it clear—this was an analytics site, not a political site.

Photo by Mark Wilson/Getty Images

And that’s how it stayed for 35 years. Once John Skipper placed a bigger emphasis on diversity—first by finding and promoting talent that didn’t look like me or Scott Van Pelt, then by funding The Undefeated—it became harder to stick to sports when sports kept colliding with everything else. When Donald Trump won the election and Colin Kaepernick began kneeling in protest during the national anthem, it became impossible. When President Trump started dividing Americans in increasingly hideous ways, it became truly impossible. And when Trump declared war on the NFL recently, it became inconceivable. ESPN couldn’t ignore race and politics because NOBODY could ignore race and politics. Especially when the president was blowing his own version of a dog whistle.

Here’s where the dual personalities of ESPN blossomed into full view. On the one hand, it’s the company that funded Ezra Edelman’s staggering vision for O.J.: Made in America, turned over a high-profile SportsCenter block to Jemele and Michael Smith, spent God knows how much on The Undefeated, throws a lavish espnW summit every fall, and does whatever else you’d want to stick in this paragraph.

On the other hand, it’s the company that found itself paralyzed when Jemele tweeted that Trump was “a white supremacist.”

Uh-oh. Now what?

This was easily one of the most flagrant social media violations in the company’s history, as well as a mortal lock to draw six to eight pages in Jim Miller’s next ESPN book. Was she deliberately provoking her critics or her bosses? Maybe. Maybe she felt so overwhelmingly frustrated—about the state of the country, about social media haters relentlessly attacking her, about how poorly ESPN was managing her show, about our race-baiting, incompetent fraud of a president—and wanted to transfer that pain elsewhere. Whatever happened, Jemele did not stumble into that tweet.

Well … wasn’t this the whole point of HAVING Jemele Hill?

She’s smart and funny and engaging as hell. Her opinions, and her life experiences that led to those opinions, are just about impossible to find in the television landscape. I always thought Jemele and Michael should have a morning show—like Regis and Kelly, but younger and hipper—because I always enjoyed when they weren’t talking about sports. I once watched them argue about cereal for 10 minutes. They could babble about anything. But when the show demanded more weight, they could handle that, too.

You know what I didn’t want to watch them do? Host SportsCenter (ESPN’s most broken show) at 6 p.m. (ESPN’s oldest-skewing time slot). Their “show” didn’t belong to them, but it didn’t belong to SportsCenter, either. Nobody was happy. (Jemele detailed as much to Bryan Curtis in September.) Within a few months, you could tell from their expressions that they didn’t love this show, either. The country changed and they changed. They had more to say. It was clear.

Did Jemele checkmate ESPN deliberately with that tweet? Was she looking for a way out? Who knows? Who cares? Three sides emerged from the aftermath:

1. I like Jemele, but she was definitely out of line. She could have used her platform for a greater good. Instead, she sabotaged it.

2. LEFT-WING ESPN IS RUNNING AMOK AGAIN!!!!!!!!!!!!

3. Wait, we have an egomaniac running our country who seems intent on suppressing the First Amendment, provoking other lunatic leaders, and dividing America. We’re really going to nitpick about tweets? We’re suppressing free speech from a diverse voice during the one year when we need all the high-profile voices we can find?

ESPN handled the ensuing hullabaloo even more awkwardly than I expected. The company didn’t support Jemele, or publicly reprimand her, or do anything other than wait for it to blow over. Two days later, she was twice as famous and there was no going back. From what I heard, they met with Jemele in Bristol and made her feel sorry for putting THEM in a bad position. I knew this was true because the company had done the same thing to me. Multiple times. When you believe you’re right and it’s handled that way, it only deepens your resolve.

How much does Disney CEO Bob Iger shape these decisions? When ESPN suspended me for three weeks (two without pay) after a 2014 podcast rant about Roger Goodell during his full-of-shit apex, I was advised a few weeks later by someone very, very, very, very, very high at ESPN that I should lay off Goodell. And not just because the NFL was ESPN’s most lucrative partner, but because Los Angeles was going to land two NFL franchises soon. And Iger wanted a piece of one of them.

I never laid off Goodell even though the tip eventually turned out to be correct. The following May, I went on Dan Patrick’s show and was asked about Goodell and Deflategate. I made a “testicular fortitude” joke that read worse than it sounded. People wrote about it. Stories were emailed up and up and up the ladder, even as I was hosting The Grantland Basketball Hour on ESPN that same night. The next morning, we found out on Twitter that Skipper wasn’t going to renew my contract. It happened that fast. I have always believed that Iger made the final call.

He’s going to be making it with Jemele Hill, too. Maybe not tomorrow, but it’s coming. She didn’t wait a month before tweeting her way into trouble again—this time, discussing a hypothetical NFL advertiser boycott shortly after her bosses warned her about social media. The company quickly suspended her for two weeks (with pay). You think that’s stopping Jemele upon her return? And why can’t I read coverage of this on The Undefeated, ESPN’s site that’s allegedly devoted to the intersections of sports, race and culture?

Hey, ESPN—WE ARE AT THE INTERSECTION. Look, it’s Jemele Hill!

Jemele’s latest tweets imagined a boycott but never advocated for one. What would happen if we boycotted NFL sponsors? How would that play out? In other words, she did her job. She made me think. ESPN still suspended her. This time around, a few colleagues defended her even as her bosses sprinted in the other direction. Why push for a diversity of voices if you can’t handle them? Please tell me that these past three years weren’t just a marketing ploy, something to be waved around for advertisers every spring, like the WatchESPN app. After the president slammed Jemele on Twitter and the company failed to defend her, it’s hard to believe anything else.

Hey, ESPN? We have at least three years of Trump left. Three! Are you a drive-thru or a restaurant? You can’t be both. When Jemele called Trump a “white supremacist,” I didn’t necessarily agree, but she made me consider it in a new light. Over the next two weeks, I read everyone’s takes, including this Ta-Nehisi Coates piece, which affected me the most. Jemele Hill got my brain going. That’s what smart people are supposed to do right now. We need dialogue. We need help. We can’t marginalize our most distinct voices.

At the Vanity Fair New Establishment Summit recently, Iger explained ESPN’s decision not to suspend Jemele (the first time) by saying, “And so I felt that we needed to take into account what Jemele and other people at ESPN were feeling in this time, and that resulted in us not taking action on the tweet that she put out.” (Notice how he used the word “I” when it was allegedly Skipper’s call. Hmmmmmm.) After the panel, Jim Rutenberg of The New York Times asked Iger about running Disney in the age of Trump.

“[Iger] told me he had his limits, including with Mr. [Jimmy] Kimmel, whose passion regarding guns and health care Mr. Iger said he appreciated. ‘That show is to entertain and, frankly, I understand him talking about Vegas, because that’s where he grew up,’ Mr. Iger told me. ‘But I think he should be careful.’”

As long as any third-rail topics directly affect Jimmy, it’s fine for him to tackle them. Otherwise, he should be careful.

What?????? Millions of viewers loved those Kimmel shows because they were authentic. Be careful? This might be Disney’s biggest blind spot now. If Iger plans on pursuing a 2020 presidential bid, as Rutenberg speculated in the same piece, then he knows that every politically charged decision from his Disney reign will get tossed in his face. Donald Trump, if he hasn’t gotten us all blown up by then, will be feasting on it. You want to lead America when you supported that troublemaker Jemele Hill? You want to lead America when you kept funneling money into left-wing ESPN? Be careful, all right.

The bigger questions: Does ESPN’s failure to back Jemele run the risk of talent losing faith in the company (and the people running it)? How will up-and-comers like Pablo Torre and Katie Nolan thrive creatively in a company that couldn’t handle Jemele? Could any ESPN talent emerge organically as a meaningful voice for the country, the way Kimmel has these past few months for ABC, or will the Worldwide Leader continue to undermine that ever happening? (Bet “yes” on the latter.) And if ESPN couldn’t govern authenticity during calmer times, what makes us believe the company could succeed during our most anxious domestic moment in 50 years?

All of it makes ESPN’s old creative struggles seem adorably innocent by comparison. In 2008, Le Anne Schreiber hypothesized that, “They may have to make niche-specific, show-specific, platform-specific guidelines that allow ESPN the flexibility to respond to changes in the cultural landscape while remaining consistent on basic journalistic values … if the boundaries are clear, there are ways for ESPN to be as edgy as it wants.”

Nine years later, it’s the funniest thing she ever wrote.

Let’s quickly tackle the Week 6 picks (home teams in all-caps) …

—Packers (-3) over VIKINGS … $550 to win $500

—Three-Team Parlay: SAINTS (-210 over Lions), Patriots (-500 over JETS) and BRONCOS (-700 over Giants) … $500 to win $503

(Coming next week: a big-ass football mailbag.)

Last week: 0-3, -$1,650

Season: 8-8, -$595