What would it take for you to leave your dream job?
John Jastremski filled in on every weekday timeslot, and he was a full-time overnight host building his own brand and following with JJ After Dark. He developed a relationship with station icon Mike Francesa and was often compared to another in Christopher “Mad Dog” Russo.
But as a lifelong listener to WFAN who was living out his dream as a radio host for nearly a decade, Jastremski was offered a new venture, one that was too good to pass up.
Few people sound more like New York than Jastremski, so leaving the city’s heritage sports radio station was surprising at first, but joining the ever-growing digital space with Bill Simmons and The Ringer presents a new playground to perform on. Creative freedom, flexibility to turn the mic on at a moment’s notice, reaching a new audience, and still being able to retain a relationship with his old listeners as he remains focused on his hometown city in a new podcast New York, New York were part of the appeal. I took some time to chat with JJ about his past, present, and future.
Brandon Contes: Just as a general starting point, what was it that appealed to you about The Ringer?
John Jastremski: Wow! Loaded question [Laughs]. Bill Simmons is somebody I’ve had a great appreciation for, for a long time. I’ll be honest, when I stepped foot on to Syracuse in 2006, I had no idea who he was, but I was living with some Boston guys who introduced me to him. And even though we rooted for different teams, that ability to be an entrepreneur and connect with fans really resonated with me. When he reached out back in December with this idea, it wasn’t like I was hearing it from a random podcast company or an upstart, I was hearing from a guy who has been incredibly successful in a lot of ventures.
BC: That’s a good measurement of talent, if you’re listening to someone and you’re not emotionally invested in the teams or topic, but you’re still able to be entertained.
JJ: Yeah! And listen, his style is very different from Mike and Chris, Joe Benigno and everyone else I grew up listening to. But he’s done a great job of developing characters and you kind of revel in the fact when his teams lose. I get a kick out of knowing he was going to be miserable on those days [Laughs]. It’s a very different sound from what I grew up with and even what I’ve done for the last nine years, but the idea of bringing a New York style podcast where I can have the same energy, same nuttiness, mix in some gambling and listener interaction on this platform is exciting.
BC: Is this move more about what The Ringer is as a platform today? Or is it about where you see them having the ability to grow?
JJ: If you look at the variety of different podcasts they have, they’re building around young talent, they’re supporting their talent, it’s great to have Spotify backing the platform as well. They’re making a real investment into the digital age and I’ll be honest, if you would have told me four years ago that I’m going to leave radio for a podcast I would have said, ‘dude you’re out of your mind!’ But it’s a different world now! So yeah, I see the company’s success and when you have a guy like Simmons saying he believes in you, it was just super appealing.
BC: This is the first New York specific podcast with The Ringer. In your conversations with Bill and the company, do they want to place a larger emphasis on regional projects?
JJ: I don’t know how they’re going to handle that moving forward. Would it surprise me if in six months they have a Boston show? No. But they may look at this as an exclusive deal to get in the number one media market and have a presence in New York. I can’t tell you what they’re thinking, but I’d be more than happy to inspire offshoots in other markets because that means I’m doing something right!
BC: Was Mike Francesa in anyway the catalyst in jumpstarting the relationship between you and Bill Simmons?
JJ: Great question because that was the first thought I had. And I asked Bill point blank, ‘how the hell did you find me?’ I thought Mike might have played a big role in that. As you know, Mike has always been in my corner, he’s always been a supporter of mine and I look at him as a mentor in many ways. This was not Mike’s doing as far as I know. It was more Bill doing prep work and research, discovering my show and taking it from there.
BC: There were only a few people ever mentioned as possible co-hosts for Francesa once Dog left. Sid Rosenberg, Bill Simmons and yourself. Did you at any point think there was a chance you could be added to Francesa’s WFAN show?
JJ: To work with Mike full-time, no. Would I have been fired up about it? Yeah. But listen, I would have forever, unfortunately, had the Mad Dog comparison because we’re both a little zany, we both have a lot of opinions and energy. Dog’s memory from 50, 60 years ago is hopefully what my memory will be about sports in the ‘90s and 2000s.
But to work with Mike, that would have forever been ‘is it going to be like Mike and Dog?’ There’s never going to be another Mike and the Mad Dog, it’s the best sports radio show in history. End of discussion. I’m grateful I was able to do a bunch of stuff with Mike, I’ll always remember that, it was an absolute thrill. It didn’t end up working out that way, and that’s OK, I’ll never have to worry about matching Dog. Now it’s my career moving forward.
BC: There was the report a while back about you not wanting to work as part of a three-person show on WFAN, was that accurate?
JJ: I never wanted to work on a three-person show. I gave it a try for a week and let me be clear, I liked both people involved, I think they’re terrific, but a three-person show to me is a lot.
But this idea that’s been out there that I wouldn’t want to work with a partner is absolute garbage. If you look at my career, I did shows with Evan Roberts, Kim Jones, Chris Moore, Brian Jones, the list goes on, and I had a blast. I very much enjoy having a partner, but it’s important for me to always have my radio show be as organic as possible. The day after a Yankees game, I know the big talking points. I want to flip the microphone on and have mutual trust with my partner that we can just go. I can’t do a radio show before doing a radio show. I’ll always be prepared, I know what’s going on, but I can’t rehearse before a show.
BC: I remember Boomer and Gio made a big deal about it, because Gregg was more of the mindset to take the opportunity no matter what, and you said if you were offered a show with a co-host that you didn’t believe could be a successful pairing, you’d decline it rather than risk it being a bust.
JJ: And everybody’s entitled to their own opinion. There are so many different avenues for people to get where they want to be. To say it’s cookie-cutter like going to school to be a doctor or lawyer, sports radio and media isn’t like that. That’s where Gregg and I beg to differ.
I love Gregg, I think he’s super talented, we’re just not going to see eye-to-eye on that. You have to believe, going into a show, that it’s going to work. And I know there will be conflict, but you have to believe in the vision. And if you don’t, then I don’t think it’s the right fit for the talent.
BC: When you are paired up with a co-host, do you take a step back to try and build chemistry or are you yourself and it’s more on them to make sure they can keep pace?
JJ: I’ll step back from time to time, depending on who you’re working with. It also depends if they’re a radio person or not. When I worked with Bart Scott, I know the nuts and bolts, so I’ll handle more of the going to calls or the ins and outs of breaks. When I work with Evan Roberts, we’ll probably go back and forth. I’m always going to be me, no matter who I’m working with. That’s how I am, I’m the same guy down the street yelling about games that I am on-air. I’m more than happy to step back when I need to, but I’m still going to yell and get into it. You just have to get a feel for how the show is going.
BC: Callers were a huge part of JJ After Dark, a huge part of overnights at WFAN, I know the new podcast is planning on taking voicemails, but without that back and forth, can voicemails have the same feel?
JJ: I’m going to miss the calls like crazy. It’s been a big part of what I’ve done over the years. I know some radio hosts hate calls, I love it and I’ll miss the back and forth. We’ll have voicemails out of the gate and I can tell you we’re working on some things. For somebody like me, it makes it more important to use a lot of platforms. I can hop on Instagram Live after a game, especially if it’s a day that I’m not doing a podcast. I’ll also utilize apps like Clubhouse, and Spotify just acquired Locker Room, because those are avenues where I can have give and take.
BC: Have you thought about trying live calls? Even though it’s prerecorded, you can tweet out the topic and number while taping to let your following chime in instead of just reacting to a voicemail.
JJ: That’s something we’re absolutely thinking about, 100%. It’s not going to be immediate, but I’ve definitely pushed for it, because I’m not going to take two hours of calls the way I would on an overnight, but for 15 or 20 minutes, I think it would be great. It combines the old school aspects of what I did at WFAN and throws in the new age platform. I’m talking New York sports, but have the backing of Spotify to get some bad ass guests, mix in the interaction and gambling, and away we go.
BC: How much will gambling be an aspect of the new podcast?
JJ: It’s a big part of what I do, but let me be clear, this is not a gambling podcast, this is New York sports, still with my same style, and some gambling mixed in. If I’m doing an hour podcast, I might do seven to ten minutes on gambling. And if I’m focused on Mets and Yankees for a show, the gambling section actually allows me to get into other topics like the NCAA Tournament. Once the NFL season starts, I’ll probably expand the gambling a bit, but it will be a case by case basis and depend on the season.
BC: With so many sports radio stations, networks, digital platforms all investing heavily in gambling, is that a content bubble you think can ever burst?
JJ: Anytime there’s oversaturation in anything, you’re concerned, but right now, there’s such a great demand for it. You’re seeing more legalization and betting companies are throwing lots of money at radio stations, TV, podcasts and even partnerships with the leagues. Did you ever think we’d be watching games and the ESPN bottom line would have betting lines and sponsors?
When I started radio in 2011, I was walking on eggshells talking about this stuff, now almost every sports podcast in America has a partnership with some sort of gambling company. I get that it’s not for everybody, but if you’re an aspiring broadcaster, you should be learning about this sphere.
BC: Sports gambling itself is obviously an endless realm of money, but the reason I wonder if the content will reach a max one day is because people listen to talk radio for personality and unique opinions. Is there an endless need for that with gambling? Do I need another gambling show or do I need another list of picks?
JJ: The idea of doing gambling content without personality doesn’t work. You need to combine personality and entertainment in a relatable and charismatic way. I understand not everybody is as zany and off the wall as I am, but you still need to relate to the audience with this stuff. Mention a great win or a bad beat they can relate to, don’t make it so formulaic. If I’m showing personality about a bad beat, even if you didn’t have money on the game, you’re still invested in the fact that I got screwed on the game. It allows the listener or viewer to be connected in that way.
BC: Do you feel that you still had room to grow within WFAN if you stayed?
JJ: I do. Listen, I had a great run there. They allowed me the platform and let me fill in on every timeslot. They gave me five nights a week. I wasn’t actively looking to leave, but this came across my desk and my jaw dropped when I received the Twitter message from Bill Simmons. It’s all about The Ringer and what they’re providing me. Do I think I could have grown at WFAN? Absolutely, but this platform and opportunity just turned out to be the next logical step for me to grow to another level.
BC: Do you mind Gio’s impressions of you?
JJ: No! I absolutely love them! I love them! I think they’re great and I hope and pray that just because I’m leaving the radio station, those impressions won’t come to an end. I learned in this business, don’t take yourself too seriously and I get annoyed when people do take themselves too seriously. You can laugh at one another, you can go back and forth, it’s all in good fun as long as nothing gets personal or vindictive. I know the radio wars get good play, but I think they can be some of the dumbest nonsense known to man. But I think the impressions are great and hope it continues.
BC: Was it you who told the story about Bob Costas giving the advice at Syracuse where he essentially said be yourself, don’t try to change your voice?
JJ: Yes, very good memory! That is absolutely true and accurate. I was super stoked when I went to Syracuse, but I quickly realized how competitive the journalism school was, even just getting on their student radio station was competitive. And I have a very unique sound.
So freshman or sophomore year I was at a student-seminar, and I asked Bob that question. I said ‘there are a lot of people here who are the buttoned up, polished broadcasters with perfect inflection in their sound and voice, is that something I have to change if I’m going to make it in sports radio?’ Bob said ‘no, if you have a sound and style, just let it roll.’ And when Bob Costas tells you that, you’re not going to do anything else.
BC: I always thought Joe Benigno wouldn’t be successful anywhere other than New York because he sounds so much like New York. Did you ever believe your style might be limited to New York only?
JJ: Interesting. I think I could have worked elsewhere. I had an opportunity about three years ago to work in Boston and I turned it down because it just wasn’t the right fit from a lifestyle standpoint.
BC: You did a few weekday shows at WEEI.
JJ: Yeah, I had a great time doing it too. I know my relationship with the audience and callers would have been drastically different. If you go to a new city, especially one that’s territorial, it’s going to take time to win them over. I probably would have been the bad guy for a while which is OK, it would have been interesting. But for the time being, I like the idea of doing New York content. I think I can work somewhere else, who knows if that opportunity would happen down the road, but at the end of the day, I’m a New Yorker through and through and that’s where I’ll be at my best.
BC: When you view the future of sports media, is talk radio still a major part of that landscape?
JJ: I think talk radio will absolutely still have a platform, but the media landscape is very different with so many avenues to stand out. The ability to listen whenever you want is paramount, and for me, the idea that I don’t have to wait until my shift to turn a microphone on is awesome. We’re scheduled to do three days a week, and if something crazy happens and we’re not planning to tape, you can bet I’m turning the microphone on even if it’s just for 20 minutes.
There’s a place for the new-age media to coexist with talk radio, I’ll always root for WFAN. That’s home and I wish them nothing but the best, but to be looking at the podcast industry as this plucky, spunky upstart, it’s just not that anymore. There’s too much money and media backing with on-demand content, it’s taken off already and I think it will continue to change in the next few years.