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Some Thoughts on Bill Simmons - Pinwheel Empire
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Some Thoughts on Bill Simmons

submitted 8 months ago by in Politics

Bill Simmons had his TV show canceled yesterday. Given his prominence, his occasionally controversial, sometimes ignorant, and frequently wrong, perspectives Mr. Simmons has accumulated a number of enemies who have no shortage of grounds to attack him. He’s got pretty retrograde views on women, he’s petulant, he’s selfish, and he’s also frequently wrong. But a read of his critics would leave you believing Bill Simmons is just a stupid guy who gets extremely disproportionate attention for writing bad opinion columns about sports. I have to be honest, I used to think this.

Now as Bill’s professional future appears to be imploding with the impending spiral of failures sure to result in him guzzling Suazo instead of Don Julio, I come to offer him the greatest salve: an admission of error from yours truly. It’s not that Bill Simmons is actually right, or even particularly insightful about sports or pop culture. In most cases, his analysis is glib, biased, short sighted, and frequently incorrect. What makes Simmons compelling despite being wrong and slipshod in his analysis is that whether he is correct or logical is frankly entirely beside the point.

Simmons singular great talent is generating a sort of Alice in Wonderland maze of references, theories, callbacks and heuristics that can be used to understand American sports. This is a structure generally built around 1980s movies, a love of losing money wagering on football in a semi-entertaining manner, and an apparent distaste for certain NBA players in the 1990s. Now the critics will say that none of this actually helps anyone understand sports. This is true so far as it goes, and for a long time I was of the opinion that this was a fatal blow to Bill Simmons’ credibility. What changed my mind is this interesting column about Donald Trump’s speaking style. The gist of the argument is as follows:

Every interaction is both an exchange of semantic information and a dance of social positioning, even those, as in science or academia, that strive to be purely the former.

To all appearances, Trump is engaged solely in the latter form of communication, and only in a narrow way: He treats all social interactions as zero-sum games establishing dominance and submission. In every interaction, someone is going to win and someone is going to lose, be with Trump or against him.

Clearly Simmons is not a Trump-like power obsessive. However, what is parallel about Simmons’writing is that the truth of what he writes is generally beside the point. The entire point of sports to him is to place them in the context of his existing heuristic, which relate to gambling, bad 80s pop culture, weird stories fetishizing college life, or maybe just more accurately, his own life. What sets Simmons apart is he was able to draw these comparisons more aggressively and more vividly than anyone. He really does draw you in to the theory that a hyped or nervous crowd, a gambling teaser, or a handsome quarterback can make a difference in a football game.

The reason these tropes are a lot more compelling than the truth about sports (which is that the team with better players and better strategy usually wins but not always and injuries make a big difference), is primarily because it just is a much better fit for how our brains are wired. Our brains want to perceive patterns, and we want to relate things to ourselves. Thus, the Teen Wolf or Meg Ryan references are a lot more interesting than something that is actually accurate. There is nothing wrong with this, since sports is entertainment, and being correct is only currency to the extent that you can make money on it. Simmons never really makes many bones about being correct, and is admittedly a farcically bad gambler.

The early Simmons descended on a landscape with little in the way of interesting and relatable sports columns. Most columnists in the 90s were old white guys who loved to make value judgements in 500 word segments. Simmons falls on many traditional tropes, but the Early Simmons was much more relatable to the average person than the average stupid sports jock. Additionally, Simmons was able to use the unlimited space provided by the internet to create constant callbacks to his theories. This has served him well in the podcasting realm, but is ultimately what doomed his TV career.

Over the nearly 20 years Bill Simmons has been writing sports columns, he essentially constantly relies on the same low-brow material. However, the way he writes about it is downright sophisticated. He constantly references old theories and references the references with updates using new athletes or teams. At his peak he would then fold this in to mailbags, where he forged a connection with readers by publishing their stories about how regular peoples’ lives (primarily relating to sex, drinking and sports watching), were governed by the paradigm Simmons himself had created. This created a rich fodder for a highly interesting and actually relatively sophisticated column. The guy clearly loves old movies, clearly loves the NBA, and clearly loves losing money on football, and it was all evident in those 5,000 word missives he’d go on.

As much as I’ve been kind of crapping on the guy throughout the column, you can see how he would be a great guy to have a beer with. He has an opinion on everything and a theory for everything. If you are an interesting person, you will have even more interesting things to say when talking to Bill Simmons, because you’ll have to respond to some question about how your area of interest relates to the ’86 Celtics or U2. These conversations, I would imagine, are what made Grantland a success. Simmons consistently encouraged his writers to draw comparisons between different subject areas, allowed massive freedom to experiment, and I’m sure prodded them to new places with his theories.

Again, this also makes for a great podcast. The podcast medium is just as much about the host as the guest in an interview. Nobody is flipping on a show for an hour without total and complete buy-in. In this environment, Simmons’ strength is keeping the conversations in territories that are interesting to his listeners, who are already familiar with his world view. It is interesting to see diverse guests grapple with Simmons’ questions and hypotheticals. When the listener is familiar with how Simmons structures the conversations, they are logical and interesting to follow. From a traditional standpoint, these are pretty bad interviews. The guests aren’t really allowed to talk that much, and a lot of the time is spent with Simmons rehashing old theories. But I think their break with tradition is what makes podcasts great. You can kind of listen to the same thing with a different twist for hours on end, and still learn a lot due to the new guests who are facing questions that are unfamiliar to them. It’s almost like the listener has the familiarity where the guest is the stranger, which is actually quite a lot of fun.

While this penchant for twisting the world into a bunch of analogies to 80s movies is highly adaptive for longform interviews, it’s exceedingly maladaptive on TV, for a variety of reasons. I’ve seen some critiques of Simmons’ show that go to the optics, or his voice, or something else. I don’t think any of this is particularly accurate. What’s going on here is that Simmons actually believes his own worldview, and is completely incapable of distilling it or explaining it in a neat package for television. Where Simmons’columns and podcasts rely on loyal consumers who are fully on the “in,” TV shows need to be able to hook people with just a few seconds of tape. When Bill Simmons is requested to provide prescient analysis on the news of the day, the results are unfocused and uninteresting. That’s because all his analysis and talent as a writer and podcaster hinges on the audience understanding 15 years of Bill Simmons content. Without this context, you’re just left with a bunch of nonsensical wrong opinions instead of entertaining wrong opinions.

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