Bill Simmons, Mike Richards, and Cancel Culture Double Jeopardy

The lucrative career of sports writer and now podcast personality Bill Simmons was born of free and unique expression. Historically, sports writers were known to impartially output facts and quote organizational sources, then Bill came along and changed the game, writing from the perspective of the overzealous fan and bringing previously unseen passion and even irrationality to the page. You might say Bill pioneered the “by the common man for the common man” approach to writing that both Dave Portnoy and Clay Travis would soon after adopt, iterate on, and master in their own right.

But back in the late 90s and early 2000s, it was Bill with his novel approach to sports writing that pushed back against the sports writing establishment and captivated audiences in the process. Like a Bill Maher or a Quentin Tarantino, Bill was a creator who expressed his thoughts freely and benefited immensely from it.

So you could see why in the late 2010s, Bill became skeptical of the creatively constricting “outrage culture” that was sweeping through the country. On a 2018 podcast, Bill lamented that “outrage culture” was “worse than ever” and “kinda scary.” He expressed sympathy for young, up and coming writers and podcasters who had no margin for error whatsoever: “You make a mistake” and then “people come at you left and right.”

Well about eighteen months after that podcast, George Floyd’s horrible death was televised on infinite loop. And whatever small window of allowable expression that still existed was slammed shut. Everyone and everything was either racist or anti-racist, no in-between. And if you were on the wrong side, angry Twitter mobs shepherded by blue checkmarked journalists might come for you. And if they did, everything you’d ever said and done was played back, and your worst moments were aggregated into a lowlight tape to be consumed by the masses on demand.

This is what constitutes journalism now.

But that sort of uncreative, packaged outrage bait isn’t the style of journalism Simmons should be into, right? More to his taste would be the “exposing powerful people doing wicked things” flavor of journalism that has been portrayed in movies like Spotlight, a film about journalists uncovering priestly sexual abuse of children, which Bill dissected on his Rewatchables podcast last fall. Bill has even quipped specifically about how digging through someone’s every word from a time gone by and adjudicating it today against a contemporary criteria is unfair and unproductive.

So you can imagine how conflicted Bill might have been when a reporter from his very own media outlet, The Ringer, dug through droves of an individual’s web content and previous legal proceedings and published an aggregation of the worst parts to This aggregation resulted in one of this year’s highest profile cancellations: the cancellation of would-be Jeopardy! host Mike Richards. 

Yes in mid-August, The Ringer reporter Claire McNear published this story to “A Smile With Sharp Teeth”: Mike Richards’s Rise to ‘Jeopardy!’ Host Sparks Questions About His Past

In the article, McNear details Richard’s involvement in a curious Jeopardy! host selection process and in corporate employment-related lawsuits as well as some offensive remarks he made on an old podcast.

Jeopardy!’s host selection process was strange, to be sure. Before being named host, Richards was already the show’s executive producer, making him responsible for choosing the next host. That is, at least until he recused himself of the duty after his own candidacy emerged. But even with the recusal, that has to be a conflict of interest, right? Richards would have had ample opportunity to either directly or indirectly select himself as host. Well even so, it wouldn’t be the first time we’ve seen it. In 2005, Miami Heat general manager Pat Riley ousted incumbent head coach Stan Van Gundy and gave himself the job. Miami won the NBA title that year.

And as for the offensive language and the employment-related disputes, as they relate to Richards in his capacity as host, dare I say, like Bert Cooper said to Pete Campbell who was trying to ruin Don Draper by verbally enumerating Draper’s past misdeeds – who cares? As the Japanese proverb goes, you are who you are in the room you are standing in.

Before the powers that be at Sony confirmed Richards as host, they must have already known about Richards’ involvement in those employment disputes involving models and pregnancy that took place behind the scenes of The Price is Right. Tabloid coverage of those incidents aside, show business is a small world, and word gets around. But Sony decided to confirm Richards as host anyway. After all, the disputes were either settled or dismissed.

It wasn’t the deeds themselves that got Richards canceled, it was the acute public outrage stemming from McNear’s article that hit the zeitgeist at just the right time. In the high courts of cancellation, there is no such concept as double jeopardy. You can be tried for your crimes time and again, so long as someone stands to benefit from it.   

And thus McNear now has the prized pelt of Richards, as well as the adulation of the establishment press, but it is the beloved Jeopardy! that is still without a host or a certain future.

But all of those details aside, the way the whole thing went down still seems wholly inconsistent with what Simmons wants for The Ringer. But once the piece was published and the genie was out of the bottle, to speak out against it or even to distance himself from it would have been to draw the ire of his woke aligned contemporaries and subordinates. So on his namesake podcast, Simmons said McNear’s article was an “incredibly reported piece” and a “true triumph.”

And thy sacrament hath been received.

You know I saw the trailer for the new Matrix movie the other day, and it got me thinking about alternate realities and such. What if in some alternate reality, a replicant McNear were writing with Simmons and The Ringer as her subjects, instead of Richards and Jeopardy!?   

What would a hard hitting distillation of lowlights to that end look like?

Maybe it would start by detailing Bill’s history of undermining and disparaging women in his writing. Like when he advised men never to give women the remote control because women can’t remember how to work the buttons. Or when he said the WNBA isn’t successful because it’s players lack sex appeal. Or when he said Serena and Venus Williams were cute in an Amazon kind of way

Then it might tell tales about how Bill is exclusionary and dismissive in the workplace. Just ask the lady whose desk Bill commandeered to store his gum and dispose of his wrappers. And look at Bill’s podcast guests from over the years, it’s just a bunch of white guys. The Old frat bros from Holy Cross.

After that, it might extrapolate out and posit whether The Ringer in its entirety and Bill individually are doing enough to foster diversity both in the workplace and in its programming. The Ringer has a lot of Dartmouth people. Have they recruited talent from more equitable sources? What measurable diversity progress has been made since Bill conceded last year that The Ringer needed to do better?

You get it.

Take all of that and drop it right as Bill’s next big venture gets announced, and you might start a kerfuffle. Would it bring Bill down? Probably not. For the same reason Jimmy Kimmel was pardoned for his literal blackface, while Megyn Kelly was condemned merely for defending the notion of it. Bill is on the right team and knows the right people. 

But then again, so did Andrew Cuomo. And that isn’t to compare the physically lascivious fondlings and geriatricidical covid policies of Cuomo to any of Bill’s comparatively mild unwoke offenses. But it does go to show, when it comes to cancel culture, your case can never be all the way closed. Just ask Mike Richards.

Written by Ethan Reese

Ethan covers digital media and popular culture after spending nearly a decade in corporate search engine marketing and digital product management


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  1. I couldn’t stomach ‘The Ringer, it’s a leftist point of view on every topic, movie, TV, sports. Simmons is a white Bostonian…a typical hypocrite of the left. I think it’s a cliche that Boston is one of the most “racist” cities.

  2. As the California recall vote showed us, it doesn’t matter if you vote against your own freedoms as long as you vote for “your team”. I used to enjoy Simmons. When The Ringer went full-woke, I stopped reading it. Maybe writing and reporting for “your team” is a valid business model. It just tells me that you have no honesty and no soul.

  3. The Ringer was a great website, for sports and culture, before George Floyd. Its wokeness was mild and easily steered around. Shortly after the Floyd incident Simmons was thrown into the lake to see if he could float. He was undone by one of his own writers, who has a Latin surname, claiming the C class was too white. Simmons capitulated.

    The site is no joy to visit now, eventhough I still pick out some podcasts to listen to. It was this event, as much as the woke deterioration of ESPN, that led me to Outkick.

  4. I’ve said it before or this site, and I’ll say it again. Simmons is another version of Letterman, Stern, Dan Patrick, and even Jimmy Kimmel. They all used to be anti-establishment, “screw the man”-type guys. I genuinely loved watching and listening to those guys 20+ years ago. They sold out, became less funny, less entertaining, and more elitist than the “establishment” they supposedly were fighting against back then. That’s why I love listening to Adam Carolla. He’s doing it on his terms, and thriving. That’s also why Outkick is my go-to for all the things the above names used to provide for me. Sports, pop culture, news, etc.

  5. The creation of Grantland and the way they covered sports, pop-culture, and the crossovers of both was a masterpiece. The Ringer had a chance to be the extension of that (especially after ditching ESPN), but instead it has gone UBER-woke and lost nearly all of its appeal. It’s extremely disheartening for the reasons you outlined. Simmons used to be a voice of the everyman and someone not afraid to speak the truth – now he and his site are primarily a sound piece for the establishment and no longer push the envelope in any way whatsoever. I used to laugh all the time reading his/their stuff. Now comedy doesn’t even exist there (nor do dissenting opinions obviously).

  6. This the same Bill Simmons that produced that Woodstock documentary a little while back that just spewed left wing bs and whined about Fred Durst, and whined about chicks whipping them out and whined about white rage. Bill Simmons is trash. Never been on one of his sites. If I wanted to hear liberals whine I’d turn on cnn or msnbc. Clay and Dave are 1000x better and put out content 10000x better than that obnoxious muppet.

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