Being Too Comfortable with Bill Simmons
Being Too Comfortable with Bill Simmons
Good morning! I’m sending the newsletter late this week due to some travel that complicated getting it out the door. We’ll be back on track next week. Quick heads up, though: I will not be covering the Harper’s letter.
Your Weekly Roundup
We start this week, with a bit of self-referential news. On July 1st, Digiday published a piece looking at the rise of Substack (the very platform bringing you this newsletter) and a “new class of newsletter entrepreneurs.” It’s a well-done summary of why using Substack has led to success for different writers and different use cases, and how some creators are teaming up to kind of reinvent the magazine using the platform. While I clearly believe in the direct connection between a creator and an audience—and more chances for readers to pay creators directly—what is still unclear is how Substack is moderated in the future should its ease of use, and its simple means of driving revenue be applied for widely spreading disinformation or hate speech.
Speaking of Digiday, they also published a pair of pieces looking at how hard it is for publishers and brands to actually quit spending money on Facebook. These articles paint the picture well from each angle. And I know this predicament intimately: I hate Facebook and have no use for it personally (and Instagram too). But as a professional, their ad and retargeting tools are a big part of user acquisition strategies and are truly hard to quit.
On the Fourth of July, the New York Times published an op-ed by Soledad O’Brien that distilled this current moment of reckoning in the media industry—a time when journalists of color are finally feeling empowered to speak up about mistreatment in the workplace without fearing retribution.
And more journalists are speaking out. I failed to link to this story last week, but journalists at the Los Angeles Times are calling for equality at their paper, as NiemanLab reported. And Vice published a deep dive on those issues and more in their look at the Los Angeles Times under the leadership of executive editor Norman Pearlstine.
Meanwhile, on the other end of the spectrum, The Daily Beast published a scathing takedown of Barstool Sports Dave Portnoy, who is a well-documented racist and bigot, as well as a group of staffers who did not call him out directly enough about his racism.
WNYC has also found itself in trouble as it tried to improve the diversity of its staff. As the New York Times reports, WNYC hired Audrey Cooper as editor-in-chief, much to the confusion of the staff there who had been looking for a leader of color. Cooper is an experienced and successful print journalist but has no experience in radio, which makes the decision even more baffling.
Columbia Journalism Review recently published an excellent special report taking a look at the history of the “Defund the Police” movement, how journalists have failed to report on the movement with nuance, and how that failure is in many ways tied to a lack of diversity in newsrooms.
In the Monday and Tuesday editions of his newsletter, The Interface, Casey Newton provided his take on the recent tech founders/CEOs vs. journalists battle that has been taking place on Twitter. I’m not well-versed in all the tweets, but Casey did a great job summarizing it and giving his usual unique (and great) take on the situation.
And, finally, on Monday, The Daily Beast, published a truly fascinating investigative story about a network of fake personas originating from the United Arab Emirates who have had op-eds placed at right-wing media outlets like The Washington Examiner and even in places like the South China Morning Post. This piece is terrifying and an absolute must-read.
What I’m Engaged With
It’s been about two weeks since the New York Times published their piece on Bill Simmons and his failure to build a diverse staff at The Ringer, the media company he founded and sold to Spotify earlier this year. And over that time, I’ve had a chance to read a lot of takes on Bill, his behavior and his shortcomings; I’ve had a chance to hear Bill’s response to the Times piece on his podcast; and I’ve done a lot of thinking myself.
As I said when the news first broke, I’ve followed Bill Simmons’s work for nearly 20 years. I’ve dreamed of working at or writing for both The Ringer and Grantland, the publication he started under the ESPN umbrella. I almost had a piece published in Grantland back in 2012 about the Belmont Stakes—as in I was literally moments away from the story running, before it was killed when the favorite in the race had to pull out due to injury. It is the closest I’ve gotten to that dream of doing work for a Bill Simmons publication or production.
I’ve listened to countless B.S. Report and Bill Simmons Podcast episodes over the years, not to mention the other podcasts Bill hosts at The Ringer or that he makes guest appearances on. I’ve listened to dozens of episodes multiple times. I grew up in a house where my parents kept Howard Stern on in the mornings, which always made his voice a source of comfort for me. And in many ways, Bill’s written work and his podcast work have been that kind of familiar voice of comfort for me.
But, as New Yorker staff writer Doreen St. Felix tweeted, perhaps both Bill Simmons and I are way too comfortable.
Bill’s response to the Times article on his podcast was more defensive than anything else. And I’m sure in many ways Bill wants to do better, has always meant to do better. Just as I am sure in many ways he doesn’t really think he’s done a bad job. He’s built his own little empire by supporting and giving a platform to his college friends, loyal members of his staff, and, yes, his own family. And it has all (generally) worked. He’s also brought young writers of color to larger audiences. I should have known about Wesley Morris years and years ago, but I only learned about his work because of Bill Simmons and Grantland. Is that enough? No, absolutely not. Does it validate Bill’s response on his podcast? No. But does it give me a glimpse into why he might be defensive? A little, I think.
In the wake of the New York Times piece, two prominent figures in sports writing shared their thoughts on Bill Simmons. The first was from Drew Magary, the novelist who is best known for his columns on Deadspin. Magary openly acknowledges the debt he owes Simmons but completely eviscerates him, finishing the piece with this doozy of a final graf:
“Now, with the entire media industry in freefall, he alone has thrived and is overseeing one of the last solvent media outlets. The Ringer could have been a haven for voices that have either been cut loose or shoved out by other places. It could have been diverse, inquisitive, rude, and vital. Given our current state of affairs, it NEEDED to be. It’s not. Writing-wise, it’s a loss leader for a podcast company. Podcast-wise, The Ringer’s mission is to be, in the words of one friend of mine, coroners of dead culture. Simmons started the company to sell it, and he did. He’s too big to be cancelled now. That is his triumph. In every other aspect, the man is an embarrassment and a f--king failure”
Henry Abbott who is one of the most prominent basketball writers and editors out there, who played a huge part in turning online NBA coverage into what it is today, also wrote a piece about Bill Simmons on his TrueHoop Substack. Abbot’s piece takes the rather odd approach of explaining Simmons’s behavior through the lens of Simmons having been raised as an only child. In doing so, he shares stories of the times he worked with Simmons when they overlapped at ESPN. The stories paint Bill as difficult, conniving, and generally unpleasant to work with—things that have been relayed elsewhere. While I believe Abbott’s stories and respect his work tremendously, it’s hard not to also read this piece as slightly petty.
That’s what I find hard about reading opinion pieces about Bill Simmons. His career is singular and has spawned many imitators; and there are others that have covered the same topics as he has with greater seriousness and skill but who haven’t reached the same level of fame or success. And because of that, it can be hard not to read the critiques of him and his missteps as another way of communicating some level of jealousy—whether that jealousy or resentment is there or not.
But Magary and Abbott have both built fantastic careers of their own, so why should they be jealous? Most likely, they aren’t. Most likely, they are just delivering firm and deserving critiques of a man who has achieved an astounding level of success, but who perhaps hasn’t done enough self-reflection; hasn’t understood what it means to collaborate; or hasn’t learned how to change.
For years, I have turned Bill Simmons and his organizations into idealized workplaces that I was only able to idealize because I’ve always been far on the outside. But, as a 34-year-old adult, I should most certainly be beyond idealizing a workplace of any kind—as well as a media CEO (or a CEO of any kind, really). I know I’m not perfect, so how can I expect anyone else to be? And how can I go through life looking for an idealized workplace or an idealized leader?
Maybe that’s something I’ve learned over the past few weeks and will take with me. I’ll still listen to Bill Simmons’s podcast. I’ll still admire how he built his career. But now I’ll hear Bill Simmons a bit differently. I won’t be as comfortable.
A Little Bit of Culture
This Week: “Goodbye Colonel” by Ennio Morricone
Earlier this week, the Italian composer Ennio Morricone passed away at the age of 91. Ennio Morricone was more than a composer, though—he was a titan of 20th century composition. The majority of his work comprised film scores, but like a good film score, his music both defined and transcended the films it was attached to.
There are days when I’ve just wanted to listen to “Cockeye’s Song” or “Deborah’s Theme” from Once Upon a Time in America on repeat, just to feel vulnerable or remorseful. And sometimes, the only sound I ever want to hear is the buzzsaw of guitar that cuts through the moaning harmonica on “Final Duel” from Once Upon a Time in the West.
But my favorite Morricone track is “Goodbye Colonel” from For a Few Dollars More. The melancholy opening clarinet notes immediately take you off guard, open your chest up. Then as the strings build and the recurring “Watch Chimes” theme emerges a sense of triumph swells and disappears just as quickly. The song becomes quiet, then begins to fade. You notice the flute for the first time, and it sounds like something has just ended, but at the same time something new and mysterious is just beginning.
You don’t need a movie when you have music like that.
The Action I’ve Taken
Due to travel and personal logistics, I did not take any action this week. I’ll do better next week.