Bill Simmons and ESPN parting ways is like ...

Bill Simmons is like ESPN.

They began, out of New England, to serve a niche for sports fans. It was just about sports and good, at times snarky, innocent fun. Eventually, they both got so big that sports started to fade into the background. The athletes and games mattered less than the entities covering them. It's not a football game as much as it is a three-and-a-half hour commercial for ESPN to advertise itself. It's not a basketball column as much as it's Simmons telling you what it's like to be Simmons at the Clippers game. The subject of every ESPN broadcast is ESPN. The subject of every Simmons column is Simmons.

As you're aware, ESPN announced that they're not going to renew Simmons' contract after it expires in September. The relevant details can be found here and here, via Vanity Fair and Deadspin, respectively.

If you found yourself surprised by the news, then clearly your life is full enough where you haven't been paying close attention to this stuff. Slowly but surely, Simmons has been angling for this outcome. He's far too smart to find himself blindsided by it. There has been a growing rift between the suits at Bristol and the fiefdom he's built in Los Angeles with Grantland. Year by year, Simmons has taken not-too-subtle steps to distance himself from "The Worldwide Leader," or at least the vast chunks of it he doesn't respect. He has guests he wants on his Podcast, writers he finds interesting on his payroll and an army of sycophants to prop up his empire.

He's gleefully accepted the Disney paychecks and enjoyed the exposure and privilege ESPN has given him, but turned his nose at the Chris Bermans and Skip Baylesses of the operation, the people who actually help the company turn a profit on television. That, in and of itself, is forgivable. But to then crusade against the NFL in general and its commissioner Roger Goodell in particular, when the league is one of ESPN's biggest partners?

That's an open, defiant act of war.

Simmons probably sees himself as a more popular, entertaining, multimedia version of "Outside the Lines," an oasis of smart, informative journalism amid endless hours of puerile drivel. What gets eyes rolling among the rank-and-file in Bristol though is that intellectually and commercially, he's always had far more in common with Bayless and Berman than with respected reporters like Bob Ley or Jeremy Schaap. The audience he's pandered to and who's made him the most influential sportswriter of our time has always been the lowest common denominator, as it must be for anyone to gain such extreme popularity.

Bill Simmons is like Family Guy.

He gained fame a decade ago for being irreverent, for being brazenly sexist and chauvinistic, and for writing that made lazy comparisons between two subjects that have nothing to do with one another. Both entities traded in crude, sophomoric humor and struggled to cobble together coherent, interesting narratives without resorting to unnecessary, cheap, self-referential tangents.

(South Park had a brilliant send-up of this years ago.)

Simmons' career was a perfect confluence of time and place. At the turn of the millennium people were just starting to discover the internet as a forum for something other than pictures of naked women. "Sports" online consisted of either box scores or message boards, which gave angry, dateless, frustrated young men an outlet to vent. His timing was impeccable. Boston isn't just a major media outlet but a mecca for sports fans who take their teams and moreover themselves way too seriously. In the early aughts the Red Sox and Celtics were making inroads back into contention after wallowing in mediocrity for much of the 90's, and the Patriots were just starting their dynasty after being an NFL laughingstock for most of their history. If Simmons came along a decade sooner, or hailed from somewhere like Cleveland or Minneapolis, would he have cultivated near the following? Of course not. Someone like him could've only come from Boston or New York.

Here are the "highlights" of a Simmons column back during his AOL Digital City Boston days. It's a running diary of the 1999 ESPY's, and by all accounts this is the story that convinced the suits at Bristol into giving him a shot.

There are bad fat women jokes, bad female athlete jokes, bad lesbian jokes. If that's not tasteless enough, there was also the line making fun of a car accident that put Detroit Red Wings defenseman Vladimir Konstantinov in a coma, temporarily paralyzed him and ended his playing career.

I know, you're thinking to yourself, "How could ESPN not hire this guy?"

It was a different time.

His writing, as unfocused and unedited as it was, resonated with people. We all watched Teen Wolf and Rocky and The Karate Kid. We all acted stupid and juvenile and irresponsibly in Las Vegas. Most of us dabbled in sports-betting (before learning our lesson) and all of us were growing addicted to fantasy sports, for the way it combined the low-stakes gambling thrill with bragging rights over friends and the satisfaction it offered to us wannabe GM's. Mostly Simmons made it seem fun, cool and socially acceptable to be a guy in your 20's who likes what guys in their 20's are drawn to, without having to apologize for it. Where old, jaded sports columnists at major newspapers and magazines openly antagonized their lowbrow readers for idolizing the monosyllabic, womanizing deadbeats who just happened to be able to run fast or hit a ball far, Simmons gave license to fans to cheer without shame.

Sports columnists have three common archetypes. Some write to rile people up, like a Bayless, a Jay Mariotti or a Mike Lupica. Some write to name drop and impress you with their access, like a Mike Wilbon or an Adrian Wojnarowski. The last group write to impress other writers. Pick anyone at Sports Illustrated or now, I guess, Grantland.

Simmons wrote to be read, by as many fans as possible, on a national scale. His target was younger men, bros in their 20's, who would go on to get cushy jobs and have disposable income in the next decade. The kind of person who wouldn't get in trouble for having ESPN.com on their work browser the way they would if it was Maxim. The kind of person who finds Rolling Stone or GQ a bit too stuffy.

He gained momentum like a snowball rolling downhill, and the bigger he became, the more he chafed with editors who tried to rein him in to the shifting corporate regulations and cultural mores. Simmons seemed to think the rules didn't apply to him because of his popularity, that he existed on an island that didn't have reverberations in the offices in Bristol filled with women and former players and coaches and general managers, all the groups he reveled in belittling. It was probably a good idea he moved to L.A. when he did.

Bill Simmons is like football.

He delivers you content once a week and when it does arrive it seems to take forever to finish. By the time you get through it, you find yourself wondering why you were looking forward to it the whole time. Reading his columns is just something you do out of habit more than anything else, a distant memory connecting to your youth. You tell yourself the games and columns were better back in the day, and maybe they were. Or maybe you were just less discerning.

I've often wondered why Simmons hasn't gotten in more trouble over the years. For example, Simmons has oft-stated that his magnum opus is "The Book of Basketball," which was 700 pages of sexism and unintended racism, with some basketball opinions intertwined for levity. The work he's most proud of contained literally over a hundred factual errors that editors had to clean up for the paperback edition.

He was taken to task for all the unflattering depictions of women in the book in the reviews, but the book was on the New York Times bestseller list for so long that the criticism didn't touch him. At least having a daughter and dealing with female colleagues in the Grantland offices has softened some of Simmons' chauvinism over the years. Having family members come out has made him more sensitive to the homosexual community.

What I've always found troubling with him is his utter lack of racial and cultural awareness. Simmons' default setting has always been to question the acumen of any African-American in a position of authority, whether it be a coach, an executive or a quarterback. No one ever calls him on this. He's always expressed skepticism that teammates of different races or backgrounds can hang out with one another socially. His go-to joke for years has been that "NBA team X acquired white player X to give incumbent white player X someone to hang out with."

I've always found his fascination with the physical attributes of the black athlete to be off-putting. How many times have we read or heard him say Kevin Durant "was put on Earth to play basketball?" How many times have we heard him theorize that if only they put their passion into that direction that an Allen Iverson or a LeBron James or a Russell Westbrook would've been "the best soccer player of all-time?" On a recent podcast with Lena Dunham, Simmons admitted he'd love to just stare at Serena Williams' body for 10 uninterrupted minutes. This is different than Donald Sterling how?

Most damning of all is Simmons' idea, which he's stated numerous times, that LeBron James and Serena Williams should breed to create the world's next super athlete.

Another word for that idea is "eugenics." The Nazis were into it. Popular CBS football analyst Jimmy "The Greek" Snyder was fired back in the 80's for explaining that the origins of the dominant black athlete traces back to selective breeding during slavery. People understood it was a bad idea to go down that road 30 years ago, before "Political correctness!"

No one has ever pointed out to him how messed up this train of thought is, and Simmons probably thinks of himself as the least-racist person around. Let's just say it has't escaped my notice that on his podcast "The B.S. Report," where he regularly books ESPN personalities, that Simmons has never had Bomani Jones as a guest.

Racist is probably not the correct word as ignorant or unevolved. He doesn't know what he doesn't know.

Bill Simmons is like pornography.

He was free and readily available on the internet and a pleasant, mostly harmless, way to amuse yourself in your late teens and early twenties. If you still indulge in him regularly in your late 30's, you likely have a skewed and unhealthy view of women and minorities.

There was no way this was going to last forever.

The thing is, as a writer Simmons knows he doesn't have it anymore, regardless of whether he ever did. Rolling Stone profiled him last year and the author of the piece submitted to Deadspin a list of quotes that didn't make it into the piece, among them this:

9) In Now I Can Die in Peace, he wrote that the shelf life of a sportswriter is eight to 10 years.
"And I might've been right, hahaha."

He hasn't curtailed his column writing because he's rich and lazy inasmuch as he just doesn't have anything original or insightful to say or angles to explore. All the 80's movies and TV shows have been mined to death. His favorite athletes have retired before some of his current readers were even born. Simmons hasn't just surrounded himself with younger, fresher, hungrier writers, but better ones, and on some level he understands this. There are only so many times Zach Lowe can politely correct one of his outlandish generalizations before it dawns on you that Simmons is a dinosaur, maybe not on the level of the Pardon the Interruption guys, but close enough for all intents and purposes.

Yet Simmons' employees are devoted to him. He gave many of them, in their mid-twenties, their big breaks. His writers have a major platform and earn good pay for their work. That doesn't happen without ESPN indulging Simmons back in 2010, the last time his contract was up.

The more prestige and acclaim Grantland was earning, the more entitled Simmons grew, despite the fact that the site was far less popular than SBNation and Deadspin, and about on par with The Onion's "A.V. Club." The particulars are detailed here, via Deadspin, so take that for what it's worth. What makes Grantland's numbers even more alarming is that Simmons' rabid and loyal fanbase still accounted for the lion's share of its clicks, not just for the rare columns he posted but also, more recently, the video podcasts.

ESPN President John Skipper pledged that "ESPN remains committed to Grantland and we have a strong team in place," but it remains to be seen if he'll stick to that stance much beyond September, especially if Simmons takes some of Grantland's best writers with him to his new venture.

I'm pretty sure Simmons got himself fired on purpose. Maybe it was a mid-life crisis and a need for something different, to rebel against authority one last time. Maybe this is the only way he could gain the freedom to say anything original. It is my fervent hope that instead of selling out to another corporate entity like Fox or Yahoo and having to kowtow to the same corporate rules of engagement of having to play nice with the other kids, Simmons stakes it out on his own, via venture capitalist backing.

I'm not interested in reading Simmons' ramshackle arbitrary rankings of basketball players, which are subjected to his recency bias anyway. I don't care what he thinks of this movie or that ballgame or some TV show. There are more talented, more nuanced, more qualified people I look to for those things.

The one thing Simmons can give us is the one thing he's been denied all these years, the right to give his unfiltered opinion on ESPN and other sports media personalities. I want to know what he really thinks of Bayless and First Take. I want to know why he shoved Wilbon out the door on the NBA Countdown set. I want jokes and insight on Berman, Stephen A. Smith, Keith Olbermann, the executives, whoever. I want opinions on talent from other networks too, people like Reggie Miller and Shaquille O'Neal and Mark Jackson and Jon Barry.

The Sports Guy is dead. Hopefully from the ashes The Sports Media Guy can be re-born. Otherwise, what's the point? Why start over to do the same tired shtick?

It's so easy and hackneyed to compare one thing to another. To go on for 2,500 words without a narrative or a point. It's terrible writing.

Anyone can do it.