John Jastremski would like you to know that he’s not bitter about how things ended at The Ringer. He also wants you to know he completely understands how these things happen, even when you don’t see them coming.
“When I’m working at a place, I always assume I’m gonna be there forever,” Jastremski told host Brandon Contes on this week’s Awful Announcing Podcast, addressing his departure from Spotify after five years co-hosting The Ringer Gambling Show and New York, New York. “And maybe that’s naive of me because, like, the business tells you otherwise, but like you’re so in it. You’re so ingrained in it, you’re like, hey, everything’s great. Everything’s going the way I want it to go. And unfortunately, business doesn’t work that way.”
Spotify shut down New York, New York in March as part of a round of layoffs that hit as many as six staffers across the company, including special projects lead Andrew Gruttadaro and staff writer Miles Surrey. Jastremski said he holds nothing against anyone involved. Companies shift their priorities, and talent must adapt when the business moves in a different direction.
“That’s just how it works. “It’s not personal,” he told Contes, quoting The Godfather. “It’s simply business.”
What he’s most proud of is how he left — the same way he left WFAN before it — with his relationships intact on both sides. He said that if he texts someone in the Ringer building today, he’ll hear back in five seconds, and that matters to him as much as the work itself.
The five years were worth it, he said, in large part because of what he got to learn from Bill Simmons. Jastremski was co-hosting The Ringer Gambling Show alongside Joe House, Cousin Sal Iacono, Raheem Palmer, and Anthony Dabbundo — a show that was airing weekdays on FanDuel Sports Network by the time the layoffs hit — as well as The Ringer Sunday Pregame, hosted by largely the same group, in addition to New York, New York, all while having direct access to one of the most successful people in the history of sports podcasting. Having Simmons invested in what he was doing was something Jastremski couldn’t have anticipated upon his arrival.
“You want to talk about somebody who’s invested in what you do, he’s invested in what you do,” Jastremski said. “Some of the lessons he gave me as far as not only being a talent — he’s your boss, but yet he’s a talent, he has his pod, he obviously has had these unbelievable successes in business — when you hear lessons from him, it matters.”
He said Simmons could not have been more hands-on throughout their time working together, and that he means every word of that as a compliment. He put Simmons in the same category as Mike Francesa, two icons of the business who gave him lessons he’ll be carrying into whatever comes next, and whose influence doesn’t go away just because the job ended.
“I couldn’t be more flattered that five years ago, he took a chance on me and that I was able to work with him for five years and take all of these lessons with me now,” he said. “Like, I feel like he’s somebody that I’ll always have a line with, hopefully, God willing.”
One thing Jastremski came away with, which he hadn’t taken for granted, was his podcast feed. The Ringer let him keep it on the way out, which he described as incredibly gracious and something he’s genuinely appreciative of. He was careful not to get into the mechanics of how it came together, or compare his situation to anyone else’s, but when Contes raised the Russillo transition as a reference point for why the feed question matters so much in these situations — Russillo famously had to start a new feed entirely when he left The Ringer for Barstool because Spotify kept his — Jastremski confirmed that framing was exactly right.
“It’s a big deal, and I’m super, super grateful for it,” he said.
As for what comes next, the honest answer is that he doesn’t yet know, and he told Contes he’s fine with that. He’s still at SNY, still putting out content, and is a free agent in the audio, digital, and gambling space for the first time in his career. He told Contes he wants to keep his New York content and his gambling content on separate feeds rather than fold everything together, because the two audiences don’t necessarily overlap the way you’d want them to.
“I have New York content that I do a really great job of. I have gambling content that I do a really great job of,” he said. “They’re kinda not elements I want to combine together into one pod.”
He compared it to how every now and again a spread comes up in a New York context — that’s fine — but he doesn’t want the gambling show to be the New York show or vice versa. The next few weeks are about figuring out who the right partners are, what the right formats are, and how to get everything into place so that when the next run starts, it starts correctly.
“I’m more than happy to join the pod, Brandon, as soon as I figure that out,” he told Contes, “hopefully sooner rather than later.”
Listen to the full episode of the Awful Announcing Podcast featuring John Jastremski on Thursday, April 9. Subscribe to the show on Apple Podcasts, Spotify, and wherever you get your podcasts. For more content, subscribe to AA’s YouTube page.
Listen to the full episode of the Awful Announcing Podcast featuring John Jastremski beginning Thursday, 9. Subscribe to the show on Apple Podcasts, Spotify, and wherever you get your podcasts. For more content, subscribe to AA’s YouTube page.
About Sam Neumann
Since the beginning of 2023, Sam has been a staff writer for Awful Announcing and The Comeback. A 2021 graduate of Temple University, Sam is a Charlotte native, who currently calls Greenville, South Carolina his home. He also has a love/hate relationship with the New York Mets and Jets.