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John Jastremski always wanted to work in radio. The Staten Island, New York, native and diehard New York sports fan grew up listening to Mike Francesa’s talk show everyday on WFAN, a radio station in New York City. He pictured himself being the next radio show host on the network.
Jastremski achieved his goal six months after graduating from Syracuse in 2010. He worked at WFAN and eventually landed his own radio show, JJ After Dark, an evening talk show where he’d talk sports news and New York sports.
“I have New York running through my blood,” Jastremski said in an interview with The Daily Orange. “It’s in my veins.”
But after working his dream job for 10 years, Jastremski left WFAN to join The Ringer, a media upstart by Bill Simmons, whom Jastremski has followed since his time at SU. Jastremski launched his podcast, “New York, New York,” last month and has appeared on numerous other Ringer-sponsored podcasts since he began working for the upstart. While podcast and radio are different mediums, he still incorporates his radio background into the podcast world, though he prefers the latter.
Jastremski’s radio background started at WAER at SU. After graduating and working odd jobs for six months, he entered WFAN’s “Fantasy Phenom” contest, where the winner received a year-long contract at the station. Among 1,000 applicants, Jastremski was one of 50 chosen to do a segment on Francesa’s show, and he ultimately won the contest.
He earned a one-year contract and began to show his abilities on the air. He was given a twice-a-week show from 1-3 a.m. in his initial contract, working part-time overnight and filling in on holidays and weekends. Eventually, he received his evening show, “JJ After Dark.”
Jastremski’s show quickly gained popularity and was shifted to slots earlier in the evening. He gained a loyal fanbase, with many listeners comparing him to other WFAN stars in Francesa and Christopher “Mad Dog” Russo due to his New York angle, strong opinions and boundless energy on air.
“I learned how to create my own brand and build what my voice was going to be,” Jastremski said. “I learned how to interact with callers, how to piggyback off of thoughts, how to plan out what each show will be.”
But in December 2020, two months after the New York Yankees’ season ended, he received a direct message on Twitter from Simmons. While Jastremski was in college, Simmons was a rising star at ESPN and Boston sports media. He started The Ringer in 2016. Simmons saw something in Jastremski, and he asked him to chat.
“Bill says, ‘I got an idea I want to run by you, when can we chat?’” Jastremski said. “I knew the minute he told me that, I was mentally all-in. You don’t say no to a guy like that.”
Simmons proposed that Jastremski appear on Simmons’ podcast, “The Bill Simmons Podcast” later that month, and offered Jastremski his own show after it was a success.
The new podcast, “New York, New York” debuted in April. It emphasizes an “intense New York energy,” and Jastremski gives quick, blunt reactions along with expletive-filled rants. Notable New York personalities such as Francesa, Jeff Van Gundy, CC Sabathia, Peter King and Frank Isola have all made guest appearances on the podcast.
With New York dominating the sports news sphere, Jastremski has discussed the Knicks and their first potential playoff appearance since 2013, the Jets’ and Giants’ NFL drafts and the start of the Mets’ and Yankees’ seasons.
“I always thought my dream job was to be the afternoon host at WFAN,” Jastremski said. “That’s evolved, and now I have this platform where it’s my show, my brand, and I’m able to do whatever I want to do.”
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