New York sports fans have known John Jastremski for nearly a decade. First, it was as a regular on WFAN. Now, they can find him on The Ringer, where he hosts New York, New York, East Coast Bias, and The Ringer Gambling Show.
I first met JJ on the same day I met a fellow Meet the Bettors star, Ariel Epstein. I led a panel they were featured in during the 2022 BSM Summit in New York. What struck me instantly about him is he knows how to command a microphone and he has just as many opinions about the business as he does the games.
JJ has been gambling since before that was a-okay by the state of New York. He has seen not only practices change, but attitudes and conversations around sports shift too. It all makes him an ideal candidate for the final Meet the Bettors column of the season, presented by Point to Point Marketing.
During our conversation, JJ and I were both trying to find air conditioning to combat the heat waves we were dealing with in New York and North Carolina respectively. We talk about what is new on boards across the country, why we will talk to kids about spreads and totals in the future like we do trades and lineups now, and so much more.
Demetri Ravanos: When you are recording, whether it’s New York, New York or the gambling show, what sort of is the attitude or the goal for gambling content at The Ringer?
John Jastremski: It’s a great question. I would say for me and what I’m trying to do with the particular pods I have is I try to make the gambling talk that we do as relatable as possible to any common man or woman that’s out there. I know that’s going to sound cliche. I know it’s going to sound obvious, but I think there’s a sentiment in your audience that is very novice when it comes to gambling. That’s okay. I mean, it’s a new phenomenon across our country and really within the Tri-State Area over the last 5 to 6 years. It’s just become far more commonplace.
We try to have fun with it. We don’t take ourselves too seriously, whether it’s me by myself or me with [Joe] House and Raheem [Palmer], we want to get things right. I think there’s definitely a little pride that comes in, but the biggest thing is we have fun talking about the games, educating the audience, and letting it rip in the best way possible.
DR: I did a session with Mina Kimes at the BSM Summit last year, and we were talking about gambling. She said, “Obviously it is not the core of what I do, but the way I understood how it mattered to me is lines were a good way of understanding just how much better people thought one team was than the other.”
Do you find that people that maybe don’t start out listening to you, interested in hearing your take before they put their money down, can still find value that way? It’s almost adifferent way of explaining analytics to people.
JJ: No doubt about it. For me, when I’m looking at games and all of a sudden, the point spreads come out, if I’m kind of like looking at it and saying, “Yeah, I think Kansas City should be a seven-point favorite against Miami,” and all of a sudden, they’re a three-and-a-half-point favorite, and I’m off by a considerable amount. The oddsmakers in the way they kind of set this up from a power rankings standpoint, are usually not wrong.
Kansas City might not be the best example because they were underdogs, I think, in three consecutive playoff games and ended up winning the Super Bowl, for goodness sakes. So maybe that’s the wrong example there, but in general, when I look at agame and have like a general idea of what I think the spread is, you’re usually not going to be that far off.
I think, a good way for a whole lot of folks to kind of look at it where you see why you think somebody is a touchdown favorite, but they’re only three-and-a-half-point favorite, is to ask “What am I missing here?”
I think the lines, without question, tell a story. Like if you think a team should be no way, shape or form an underdog and they are, usually Vegas and the oddsmakers aren’t wrong about that sort of stuff.
DR: You mentioned that gambling is pretty new to the Tri-State area. It has been a theme that everyone I’ve talked to in New York has complained about the differences in restrictions between New York and New Jersey and Connecticut. So, I wonder what restrictions has New York specifically put on bets and gambling that just don’t make sense to you?
JJ: Now, listen, I’m not going to be able to speak to whatever the high rollers are dealing with, you know what I mean? I’m not sure what they’re not allowed to do and whatnot, but I’ll say this. From like, a state-by-state basis, I know it’s especially annoying for a lot of folks in the New York area being unable to bet awards, MVP or Cy Young in baseball. You can’t bet on that stuff in the state of New York. If you go to Jersey and you go to Connecticut, I think you can bet on it there. Why that’s the case? No idea. That’s something that I think is a bit frustrating. But, you know, that’s kind of above my pay grade as far as why they made that decision.
DR: Listen, that is the majority of what the complaints have been. The things that just aren’t on the board in New York. Speaking of what’s on the board in New Jersey, any interest at all in betting Car-Jitsu?
JJ: You have to explain to me what it is. I don’t even know.
DR: I stumbled upon this the other day because a bunch of people were talking about it on Twitter. It is basically like a street fight, but inside of a car. New Jersey just made it legal to bet on this thing.
JJ: Oh my goodness! I mean, listen. Unless I can get some insider information, maybe you can make me a box. I love betting on sports, don’t get me wrong, but this is a hard pass for me on this one, Demetri. I’m not gonna lie.
DR: We see eye-to-eye here. This felt like one of those “did New Jersey find the end of the Internet?” situations. Are they so bored with every other sport?
JJ: Hey, listen, you put it up on FanDuel, you’ll find somebody who’s taking action.
DR: Do you think gambling will be a part of how you experience sports with your kids? Maybe your toddler isn’t asking you to put money on the Yankees’ over, but do you think it would be part of the conversation about how the game is played?
JJ: Yeah, I think it’s inevitable at this point. And it’s not just me and how I’m doing content and how I’m doing shows. Think about just watching The Bottom Line on ESPN now. Every single game features a spread and a money line. So, it’s kind of inevitable that if you’re going to have your ten-year-old son or daughter say, “Hey daddy, why are the Yankees -165? What does that mean?”.
It’s like anything else that becomes so much more mainstream. You have to do it responsibly. You have to have limits and whatnot, but I think we’re in a culture now with sports and gambling where it’s just so intertwined, and I’m sure that’s going to be true for a whole lot of young people.
You can’t escape it, but you know, it was always a part of the fabric of sports. Point spreads have always been a thing. It’s not like they came out five years ago in the NFL, but now it’s bigger than ever before, and these mainstream brands have made it part of their vernacular more than ever before.
DR: With it becoming so much a part of the mainstream, how do you as a gambler feel the odds projection content on pre-game shows has been handled? Do you feel like you’re getting served? Do you feel like it’s too dumbed down for someone like you to get anything from because it’s catered to inexperienced gamblers?
JJ: For the experienced gambler, they’re going to want numbers. They’re going to want as nuts and bolts as you’re going to find and sometimes that’s just not entertaining. I totally understand that, and that’s why, to me,it’s a fine line on how you discuss it and how you present it, at least from my end.
I think we try to present numbers but be as conversational and as fun as you possibly can be, because if you just start throwing out a zillion numbers at your audience, you’re going to lose them. It’s going to become way too complicated. It’s just bad content.
I think the experienced gambler, to be perfectly honest, they’re going to make their opinions and do their homework, research without the help of us. You know what I mean? You could have a sharp and as hardcore X’s and O’s type of show, but I think for the hardcore gambler, they’re going to trust their research. They’re going to trust their models and homework and whatnot and kind of go from there.
DR: Can you imagine the sports content at The Ringer without the gambling element? You mentioned yourself and your partners on the gambling show, but you also have Cousin Sal. You have Bill. Everybody there looks at sports through a gambling lens it seems.
JJ: No doubt. And that was always something that was very appealing to me when it comes to working with Bill. When he called me back in 2012, he had been doing this on his podcast with Sal, geez, since I was in college. I mean, going back to when people didn’t even know what a freaking podcast was!
2006, 2007, they’re guessing the lines on the NFL games, so it’s definitely a big part of what a lot of us are doing on our specific shows. It’s obviously a big part of what I’m doing. I kind of look at my New York show and my gambling show in two different lights. I’ll do some gambling on the New York show, but it’s going to be more content driven, and we take it from there.
Our podcast, East Coast Bias, with House and Raheem, is far more “Hey, let it rip. Here’s what’s going on in the country and sports. These are lines for NFL, NBA, college” and kind of take it from there. But yeah, it’s a big part of what we’re doing across the board and it’s definitely a big part of what I’m doing. So, I guess to answer your question, no, I could not imagine our platforms and what we’re doing with, you know, the FanDuel partnership and whatnot without gambling being a thing, dude. No doubt.
DR: Let’s talk about sites like Prize Picks. They kind of reframe the old daily fantasy model, and obviously that particular site has had success. But for you, I wonder if it’s possible to mine that kind of stuff for content, or as long as books have prop bets available, will daily fantasy always kind of be behind the eight ball in that way?
JJ: I kind of get the sense that, yes, they’ll be behind because the books are just so good now when it comes to the props, and it’s become such a big part of what kind of takes place in the gambling space. I’ve always been a sides guy. Like, I was never a guy that really got involved with betting guys to hit home runs or taking the over on strikeouts and points.
But, you know, what ends up happening is you’re doing daily content or weekly content, and we’ve got to put together a four-legsame game parlay on a Yankee game. So, I’ll end up finding myself looking into that market a lot more than I used to. You know, you kind of hit the end of the NBA season where, “Hey, we have a pod that we have to do.” Well, you have one game that you’re talking about, so, you know, you can’t just rely on saying, “all right, who do you like?” You got to kind of look into Derrick White three-pointers made or you got to look into Al Horford rebounds or whatever.
I think the prop markets now, for all of these sites, they’re such a big part of what they’re going to do. I don’t get the sense that’s going to go away. I know, for me, it’s become a bigger part of what we’ve discussed because listen, it’s no days off with this now, you know? You have a show to do. You’ve got to do good content. So, the audience is counting on it from you in that respect.
DR: Have you thought about, how you are going to handle the Olympics from a gambling perspective?
JJ: That’s a good question. I haven’t. I’ll be honest, the basketball I know I’m going to be into. The other sports, I’m not going to have the slightest idea of what I’m doing.
Maybe I get into the golf, maybe I’d consult a buddy of mine on the tennis, but, you know, I’m not going to pretend that I’m the master of handicapping swimming or track and field. I don’t even know if they’re putting lines on them. I’m sure they are putting lines on that stuff, but how to read it and how to play it? I mean, I couldn’t tell you what’s what.
So, you know, the way I look at it is, “Hey, Olympics are in a couple of weeks.” We’ll see what’s in front of me, and we’ll try to navigate sport by sport what we want to get involved with and what we should probably avoid.
DR: I am going to need a text message if you decide to put some action on Olympic breakdancing this year.
JJ: Oh, yeah! Absolutely, I gotcha!
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