The Downfall of Bill Simmons and the Rise of New Media, Part 1

Major league American sport is sports media, and the media is American culture. Before the internet took over from the fake news, it took over sports media. This is why those outside Bill Simmons’ fan base should care that his HBO show was cancelled.

Simmons was one of the internet’s first success stories, making the leap from blogging to podcasting to running his own website to TV. Simmons was released by ESPN just as the internet came of age and became the new mainstream. What went wrong? What can other internet luminaries learn from his failure?

Writers like Simmons used sports to explore styles of sports writing such as long form analogy pieces and listicles, that embraced the advantages of the medium. The technology allowed for innovation, for example, links allowed obscure extended metaphors andthe use of short clips for humour. Tech innovation led to writing innovation.

As ESPN’s Sports Guy he was a blogger before for AOL subscribers. He wrote in an opinionated editorial style. For a while he was positioned as an alternative to the straight journalism of the main brand. He was the ‘net nerds insider in a world of alphas, extroverts and jocks. He brought obscure pop culture references and extended, tenuous metaphors in a style that imitated college friends talking about sports in a bar, a style perfected on his The BS Report. He used references from RockyThe Karate Kid and Teen Wolf. The internet facilitated this style, and also allowed for a sense of contuity between stylisiticly relsted articles. Search engines, Wikipedia and pre-copyright YouTube allowed for an expansion of what could be referenced, implied or used by way of analogy.

As the internet grew Simmons audience expanded and culminated in making The Book of Basketball: The NBA According to the Sports Guy a massive success that earned him considerable clout at ESPN, ultimately leading in Grantland, a sports/pop culture journalists creative playpen. He made the transition for sports blogger to TV personality behind the scenes with the 30 for 30 series, then in front of the camera on NBA Countdown and The Grantland Basketball Hour. His love of hip-hop was novel in a time when the NBA was actively suppressing players being too hip-hip. Referencing 2Pac or NWA was edgy. Simmons is now a nearly-50 year old man who gushes over every new hip-hop act like an awkward dad trying to relate to his son.

How could one man go from pioneer of a new kind of media empire to out of touch in such a short time? For Simmons readers, the disease of more might sound familiar.

Whether Simmons knew it or not, he had lucked onto one of the most sustainable, low-overhead, high exposure double as a podcasting sportswriter. Unfortnately, growing up in old media meant his vision of success was defined by an outdated model, and his downfall was a result of his failure to update his vision.

Grantland was a way for the ESPN dino-media to keep Simmons and his kind at arms length. Simmons seemed happy, but kept working on his plan to his vision of a variety show. This was probably the result of his work for Jimmy Kim Mel. 30 for 30 was a success, but in front of the camera Simmons was a failure. He is a good writer whose style has become ubiquitous to the point of overexposure, and his references have become dated. He has become an imitation of himself.

The Book of Basketball will likely be his legacy. His threats to update are (ironically) more in keeping with a website. A book should be a reflection of the time of its publication, a time that was Simmons’ creative peak.

But then he had to go and try to be a real journalist, even if it was out of pride, and tackle the NFL and Roger Goodell.


The story is adequately covered in Business Insider, Vanity Fair or Deadspin.

Simmons was a victim of the dino-media. Simmons contract itself is evidence that ESPN did not understand how to quantify internet popularity. He was continually at war with John Skipper, like a conservative working for CNN or the Washing Post. In his attempts to question the NFLs handling or the Ray Rice controversy Simmons was suspended, then later let go faster than a New York Times writer criticising Carlos Slim. Simmons is either the victim of a conflict of interest relating to Disney’s ownership of ESPN and other companies like the NFL that prevents it from effectively reporting on  controversies like domestic violence and concussion related injuries in the NFL, the internal discplinary procedures of the league and the nature of Goodells authority, or of  ESPNs desperation to ditch his exorbitant contract to save money because its social justice friendly objectives have left the company unable to pursue its corporate mandate of profitability. So essentially, fake news, or SJWs.

Such corruption, obfuscation and conflicts of journalistic integrity were rife during Trump’s campaign, and the aftermath has brought into question the very nature of establishment media. One might think Simmons would notice such parallels. This corruption is a 2oth century virus the dino-media is attempting to infect the 21st century with. Social media is the cure.

Simmons was an internet pioneer who used an established platform to build his own personal brand, through a multimedia approach. This is the template for all internet brands. Following his departure I eagerly awaited the launch of his new website to replace GrantlandThe Ringer. Any Given Wednesday was to replace The Grantland Basketball HourThe Bill Simmons Podcast replaced The BS Report. Backed by HBO, he had the time and the money to build his vision of what ESPN had always held back. Simmons was out of excuses. All this has meant Simmons no longer actually writes…

His failure to transcend his former persona has left him. His attempt to recreate the echochamber he built at ESPN was a little too familiar. His revenge on ESPN has failed, because they both follow the same misguided social justice agendas. Simmons has failed to differentiate his product from the mainstream at all, at best promoting a kind of liberal predictability that only seems creative to journalism majors who love Rolling Stone. It lacks the testosterone of the old-school coverage, but also any edgy counterculture elements. It is a safe product, about as edgy as the rebels in Disney’s Star Wars or Lady Gaga. This is what controlled opposition looks like. Like an indie band signing with a major label, Simmons has alienated the non-mainstream internet with his lazy politics. As noted by Vox Day in a recent periscope, sports journalists seem to virtue signal to ‘real’ journalists for legitimacy. Chasing lowest common denominator numbers is the old way.

Simmons mistake was attempting to recreate his old platform, his old vision, rather than be a true visionary and come up with a new one for a new time. Embracing a cable station that would own your video content just as everyone stopped watching TV is like trading in a T-model Ford for a luxury horse and carriage.


The pattern of 20th century media and culture was to co-opt and corrupt every countercultural movement or revolution and render it a meaningless husk. In the ’90s Grunge, Marilyn Manson and rap music were all symptomatic of depression growing into frustration, shouts for attention to neglectful parents, manifested as nihilistic rebellion or rejection of Western culture, co-opted into the next trend; frustration that gave form to a new cry for help – the school shooting. The mainstream assimilated all as it grew, like Akira.

It was not until the internet destroyed the music industry that people took notice. The technology made the choice – music files were smaller than videos. The internet has changed the way we watch TV. Hollywood has felt the economic hit, and has taken up arms against the internet, which has exposed them in every way. They know their industry is next. The internet had become the best way for athletes to built their brands. Conor McGregor’s use of twitter and podcasts with Ariel Helwani to promote himself has made him the biggest draw in modern sport.

In 2016 it was the news media industry that the internet chose to destroy. And it did it on the grandest stage of them all – the Presidential Election.

Part 2


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