Bill Simmons has many ardent fans who’ve followed the sportswriter and podcaster through the years, but some people believe he has, euphemistically speaking, “lost some of his fastball.”
The Ringer founder and former ESPN personality airs his views on The Bill Simmons Podcast. Several prominent sponsors back the podcast and Simmons reads their promotions. Some fans have noted that Simmons’ pitches sometimes come off as inauthentic. Specifically, he will often spend one ad read trashing a business only to turn around and praise it in the next.
This take will appeal to maybe six people but I’m loving Bill Simmons doing ads for Airbnb where he makes fun of hotels, and ads for Hilton where he makes fun of home rental sites, both in the same episode!! no one is doing it like the old man.
— Little Orphan Funkhouser (@BLymanWarrior) December 20, 2023
Bill Simmons doing ad reads for Hilton AND AirBnB https://t.co/4SaSuxWtdU pic.twitter.com/2Ngc8jAaO4
— The r/BillSimmons Podcast (@rBillSimmonsPod) December 20, 2023
It's so funny when I get back-to-back @BillSimmons ads for AirBnb and Hilton.
"Why worry about hotel people when you can have a whole house to yourself?"
"Why deal with a random host when you can have the support of the whole hotel staff?"
— Ramon (@PQyosoymoreno) December 20, 2023
The r/BillSimmons Podcast, which debuted earlier this year with a mission to critique Simmons’ podcast, pointed out that issue this week, noting he has a conflict of interest with some of his spots. The podcast brought on a longtime Simmons fan, “Richie from Twitter,” who roasted Simmons on the topic.
“The Airbnb [promotion], where he reads, ‘Oh, Airbnb has bailed me out so many times … you don’t have to see anybody, you don’t have to deal with anybody, you go in, the place is yours,” Richie said. “Then he has the read for Airbnb where he talks about renting out your own home … ‘What’s your house worth? Check with Airbnb.’
“Twenty minutes later, the next break, the next ad read is for Hilton. And what does he say in the Hilton read? ‘Who wants to deal with looking for a key under a pot or the mat or fumbling with a lock box in the middle of the night. … You know what’s great about Hilton? There’s somebody available 24/7.’
“Wait a second, you are literally going against everything you just said 20 minutes ago. Both of these companies are giving you money and within the same structure of the pod, you’re bashing the other company.”
Richie, who noted he’s a Simmons fan dating to his Page 2 days at ESPN.com, said he’s baffled by the apparent conflict of interest.
“Can you make this make sense for me?” he said.
We discussed exactly this on today’s pod! https://t.co/xE8EfRObLu pic.twitter.com/i8xybntSMo
— The r/BillSimmons Podcast (@rBillSimmonsPod) December 20, 2023
It’s worth noting that advertisers are usually quick to point out these types of conflicts; if they have an issue, they will definitely request changes. But advertisers also love their pitch to come off as genuine, and some fans think that’s an issue with Simmons these days, and it goes beyond his promotional spots.
People have noted the competing ad reads for a while now, so it sounds like they’re fine with it. Or they’re not listening. For all we know, Simmons is doing it on purpose at this point.

About Arthur Weinstein
Arthur spends his free time traveling around the U.S. to sporting events, state and national parks, and in search of great restaurants off the beaten path.
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