Life After SI

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1:05Congratulations! You made the varsity of the podcast. My name is John O 'Ran and I am Puck's sports correspondent and the host of this pod. And today's going to be a fun one. Jimmy Trana joins the pod. Now, Jimmy has been with Sports Illustrated for more than 20 years. And just last week, he announced that he was leaving to start a New York-focused media company with a couple of guys from WFAN. So we're going to spend a lot of time just talking about the business. I like Jimmy. This is going to be a good one. But before I get to Jimmy, today is Sunday, August 23rd, and I want to highlight the In the Arena conference that Puck is putting on with Moffitt Nathanson.

1:40It's going to be held October 1st in New York, and we have a stellar list of speakers, including the head of the NCAA, Charlie Baker, and the head of the SEC, Greg Sankey. The content chief from Netflix, Xpela Bejeria will be there, and so too will NBCU head Matt Strauss, NWSL commissioner Jessica Berman, and plenty others. Go to puck.news for more information. And before I begin, I want to highlight a statistic that I wrote about in my private email last week. It was about a month ago that ESPN published a story that quoted the Indiana Fever's Sophie Cunningham on her position that women shouldn't have to compete against biological men.

2:19Her comment created a firestorm, and for the The past four weeks, the focus around the WNBA has been on the country's culture wars and not on the competition on the court. But guess what? In those four weeks, the WNBA has seen its TV ratings rise by 20 percent. All of the attention around the sport, even negative attention, is helping the league's TV numbers. But this is what I found most interesting about that. Media executives don't love it. They love the added viewers, of course, but this rise feels like a fad, like when Colorado games became hugely popular when Deion Sanders first became coach.

2:58Media executives believe in the sport. It's perfect for the slow summer months, but they want growth to be steadier. It's something to keep an eye on. Okay, now let's get to Jimmy Trena. Jimmy Trena, first of all, thank you for joining the pod here. you uh announced on twitter and then saw a couple of stories out there it hit like a thunderbolt because you have been with sports illustrated for about 20 years and you announced that uh uh you are leaving sports illustrated to set up your own shop uh underscore media uh which is going to focus mainly on on new york sports but i think what i want to do is i want to get into to your decision-making about why you left SI, what went into the decisions to make SI.

3:52I was just, for context, I was at Sports Business Journal for 18 years, and that's when I ended up leaving to go to Puck. And it was terrifying. I'm very happy I made the move, but at the time it was totally terrifying to make that move after almost two decades. You were a little bit more than two decades. Take us through when this started. Just tell me the story about it. Sure. Well, first of all, thanks for having me. It's an honor to be on the varsity. You know, I'm a big fan of yours. Read your stuff on puck. So thrilled you asked me, especially at this time, because I need to let everyone know they need to subscribe to my new podcast because I wasn't taking the feed from Sports Illustrated.

4:33So I appreciate you having me on. Um, the decision was not something that came quickly. Um, I would say for probably two years, at least I have been wanting to stop writing five days a week. I've been writing five days a week a daily column monday through friday since 2007. and you know we have jobs where no one ever wants to hear us complain about our jobs we're sort of in the playground covering sports but when you wake up every single morning and have a blank page in front of you and you have to fill it. There's a lot of stress there because you don't want to shortchange people. You want to give them a good column.

5:29And I don't know how you give people a good column when you're doing it five days a week. We're covering sports media. If I covered a league, if you cover the NFL, yeah, you could probably write five days a week in your sleep, but there's not sports media news every single day. So for a long time, I sort of wanted to get out of the five days a week

5:53writing ritual. That coincides with seeing how the business has changed. And I'm probably late on this. I mean, you can make the argument I should have made a move maybe two, three, four years ago, just because there is a move in this business, whether you like it or not. I don't like it, but this is what it is. It's all about YouTube, reels, TikTok. that is, I felt, where you need to sort of be. And I was only doing one pot a week at SI. I don't think we maximized the clips. I don't think we maximized the promotion for it.

6:35So at that time then, you know, with all this in my head, then this startup media company, Underscore Media, pursued me and they want to do the things i want to do more podcasts less writing you know the days of trying to get google search seo headlines like those days are over um there's other avenue revenue streams now you know live events watch along stuff like that i'll probably be doing those um so it was you know i think when you leave a job and you you know i'd love to hear what you thought when you left sports business journal but when i when you leave a job it's not for one reason i don't think i mean unless there's an issue you know we saw that seattle columnist this week leave because they killed a column or something like that but for me it was the the way media consumption has changed it was wanting to do less writing more podcasting uh going to a startup where I'll have way more freedom and, you know, long time at SI and, you know, looking for something different.

7:46You know what I find fascinating about your answer is I follow you, right? I follow you on social. I read your columns. I listen to your podcast. I saw you put this on X when you announced that you're tired of writing five days a week. God's honest truth, I was like, he writes five days a week? You're known so much more for your podcast, it seems, and for your social feeds, it seems. When did that change? When did you sort of notice, because I'm sure I'm not unique in viewing you that way, when did you get that sense that that had changed? Well, first of all, I'm happy to hear you say that because that sort of justifies the move that I made.

8:36I would say, so I took over the sports media podcast, Sports Illustrated from Deitch in 2018. I would say, I would say, I think, how did you word the question? When did that shift where people knew me more for the podcast? I would say that happened, started to happen in 2020. And bizarrely enough, not a good phrase here to use, but thanks to COVID. Because before COVID, we didn't post video of my podcast. It was audio only, you know, Apple, Spotify, et cetera. Then COVID came. We all became trapped in our houses. And, you know, I feel like this is a majorly, majorly underrated media story. It was COVID that made everyone become video podcast people.

9:30We started doing them on Zoom. You know, before COVID, I would be in a studio. And in fact, even beyond that, it was COVID that made people accept video that wasn't from a, you know, billion dollar TV studio. It's like, oh, you know what? And high quality. I can take. Exactly. I can take a Zoom interview or I can take like, and you're even seeing that show up now on ESPN and Fox. You know, Mina Kimes from her kitchen sometimes calls in to, you know, NFL Live. Yeah. So the podcast before COVID, I'd be in a studio in the SI office, excuse me, and the guests would be on the phone. I haven't done a phone interview.

10:14I can't remember the last time we did a phone interview. Now every interview is on Zoom or we use StreamYard. So I think it was that. And COVID was, you know, a weird time because there were no sports going on. So I think I got a little bit outside the box during COVID. I had Steve Schirippa and Michael Imperioli on one episode to talk about their Sopranos podcast. I mean, Keith Hernandez did the podcast. He sat outside in his backyard in Sag Harbor. I remember that being kind of a... I had Stephen A. Smith on. He did it from his car with the sun beaming in his face. So you make a great point about how, you know, you didn't need this high-quality network-type video.

10:54And then also I have to give a lot of credit with the segment I started doing at the end of each pod with Sal Akata, who's part of Underscore Media, with me. I sort of – I almost underrated – I didn't realize how much people enjoyed that segment. It was basically the person in charge of podcasts at Sports Illustrated came to me one day and said they want you to do a segment. I had always – I wanted to avoid segments. I think segments – I wanted it to be different. When I started Hot Clicks, I wanted it to be different. I didn't want it to be the same. I feel like every podcast does segments, and they have these, you know, hokey names, and it's let's, you know, do this segment.

11:35And I just wanted to have conversations. But they said, we want you to do a segment. So they wanted to take the column, the train of thoughts column that I wrote five days a week and make that sort of a segment. But I didn't want to do it solo. I wanted to bring someone in and they wanted me to use, I think, you know, someone at SI, which I didn't love that idea because I wanted it to be someone I knew and had chemistry with. So it was my idea to bring in Sal because Sal does radio. He was on WOR, WFAN. He's on SNY TV. um and when this will tie into your first question i because i should have mentioned this sal was unceremoniously let go by wfan in december of 2025 and he told me in his in his journey looking for a new job and talking to people talking to agents talking to executives people in the business he basically said every single person said to him love this segment with you and Jimmy, that should be its own show.

12:31You guys should be doing something more with that, et cetera. Meanwhile, at Sports Illustrated, they wouldn't even post that video on YouTube. So that was part of all this as well in terms of your first question and second question.

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13:32T. Rowe Price Investment Services, Inc. What the heck is going on with all these promotional popcorn buckets? The giant shorts that all of Gen Z is wearing now? And whatever the heck High Rocks is? I'm comedian and certified hater Matt Bellassi, and these are the types of questions I'm demanding answers to on my podcast, What the Heck with Matt Bellassi. Listen or watch every Thursday as I rant about all the internet trends, pop culture stories, and personal mayhem that makes me scream, what the heck? Follow What the Heck with Matt Bellasai wherever you get your podcasts. When I left Sports Business Journal, Puck was only a couple years old, and I knew what Puck was, but it was just kind of new.

14:16And I have to say, I'm old school. I prioritize brands. And so the idea of like Sports Illustrated of 2026 certainly isn't the Sports Illustrated of 1996. You know, everybody certainly knows that. But the Sports Illustrated brand still resonates with something like sort of deep inside of me. I'm convinced that one of the reasons that it was tough to leave SPJ was the SPJ brand. It's been around since the 90s. You know, I feel like I helped build it up, you know, and it was difficult to leave that. you're leaving Sports Illustrated to go to something called Underscore Media. Walk me through the pitch.

14:59How did they talk you into doing that?

15:03Well, the person behind Underscore Media, Steve Hirsch, he runs a firm, a media and PR firm, Hirsch Leatherwood. They've done PR for the Mets. I know they have some connections to the Omaha productions, which is obviously huge in our business. And the pitch was really, they wanted me. They wanted what I've done. They love the podcast. They love the way I do the interviews. They love the segment with Sal. And they pitched me on this idea of joining the team that was going to start out small and focus on, you know, Sal and John Jastrzemski, who's a part of this will focus on the New York angle of things.

15:46They don't want me to do that. They want me to still do national. Obviously, listen, I'm a Yankee fan, as you know. The Yankees are in the playoffs. I'm sure you'll see me doing some things. By the way, that was a total fair ball that Alonzo hit. I mean, by every angle, it's going over the pole. I mean, come on. It's cold foul. It's cold foul, even after replay. Not quite to Jeffrey Mayer levels, but, you know, still bad enough. But anyway, I interrupt. Go ahead. definitely um and you know i don't know you might not have had this to the extent i did and i'm not saying this in in a negative way in any shape way shape or form but it's just the reality when you are at a brand like sports illustrated there are certain rules there are certain standards there are certain things you may not cover or certain things you may not say a certain way and at underscore media here they've told me do whatever you want basically i you know if i it sounds like a dream job we'll see yes exactly exactly um you know listen i'm not going to be that listen maybe you were getting 50 of my personality at sports illustrated and maybe now you'll get 75 of my personality at underscore media um because you are representing a brand i mean listen i'm representing underscore media so i'm not going to go out there and just say crazy stuff for the sake of saying crazy stuff that's not going to happen but i can sort of push the envelope a little bit more which appeals to me for sure so what does that mean like what are we going to see I just want to say they also when I said they also I had said to them I love I complain about the podcast because I book it so people but when I do this when I just have the conversation I love this so I said to underscore that I really too would like to expand outside of sports if I want to have a stand-up comedian on the show or an actor or Or, you know, even someone from TikTok who's going viral, whatever it is.

17:57And green light, go right ahead. So, you know, at Sports Illustrated, I would think twice if I'm doing the Sports Illustrated media podcast with, you know, Bill Burr. You did the Sports Illustrated media podcast with The Sopranos. Was that hard to push through? or did you just do it and ask for forgiveness later? No, well, listen, it was during COVID. So anything went during that time period, number one. Number two, I want to be clear. No one from Sports Illustrated ever came to me and said, you shouldn't have that guest or you can't have that guest. But I could see in the way things got promoted or not promoted, if you didn't have a sports guest it might not get promoted as much all right so i'm going to try to pin you down on underscore media how often are you expecting to do the podcast how often are you expecting to write you mentioned live events what am i going to be able to watch a yankees game uh with you like a bar meetup or something along those lines Take me through what consumers should expect.

19:16Well, first, it'll be three podcasts a week. They will be free. Per week. One podcast will be the podcast I've always done where I interview you or Deitch or Martian or a broadcaster, Joe Buck, Jim Nance, Al Michaels. The same exact pod, the same exact interview that I've been doing since 2018, that will be one episode. there'll be a second episode that will be the train of thought segment that i was doing with sal we're going to do that as just a separate episode and that segment will be the same as it was when we did it at sports illustrated nothing changes the only thing i could change is we can go maybe slightly longer we used to stick to like 20 25 minutes now maybe we go 30 40 minutes um so that doesn't change either and then there'll be a third episode that'll be sort of like a wild card it It could be just me talking about sports media news of the week.

20:08It could be another interview. It could be anything. It could be someone outside of sports, inside of sports. We're going to see how that goes. And I'll be doing a newsletter twice a week covering sports media. And in terms of live events, we haven't sort of hammered that out. I don't know if it'll be me in person or like Zooms or something like that for subscribers. but you know i'm sure sal and i'll probably do a live podcast somewhere we've gotten a ton of requests because sal and i are both from long island um my listeners like do a do a live podcast from maureen's kitchen which is this famous breakfast place on long island so i'm sure you'll see us do something like that i wish i could give you like a more declarative answer on that stuff but my focus right now is on the pod which will be all on youtube as well i think the show with sal we're going to do that live on YouTube and then obviously it'll be on Apple and Spotify.

21:05YouTube's obviously going to be a huge part of this for the interview I do and the show with Sal. So everything will be on YouTube, Apple, Spotify. And that's really where the main focus is till we get launched. And I get a couple of episodes under my belt. I want people to understand nothing's changing with the tone of the show and my interviews. I want people to understand I'm still going to get phenomenal guests. I've heard from so many people in sports media, so they're still going to come on and join me. So you're not going to see anything radically different. You're just going to see more pods, more video, more clips and less writing.

21:39And what about a start date? When should we expect this to come out? I think our official start date is September 8th, which is the day before the NFL season, because you know this in our business, everything revolves around the NFL season. I would say, though, keep your eyes and ears open to social media. You may get a surprise before September 8th. This is going to be my favorite question because I'm going to talk about how you disappointed me so dearly. I can't wait to hear this. Your time at Sports Illustrated, you put yourself out as like the everyman. And, you know, you wrote a column and you came out, you had opinions and you specifically did not attend events.

22:27You specifically did. I think you did talk to some PR people, but they had no idea what to do with you because you weren't like Marchand and you weren't like like me, you know, sort of calling. Right. And then every August, CBS Sports holds a NFL meeting. And I go all the time because the executives are there. Where were you this year? I missed you. Oh, you know what? I was out in California this year. Yeah. But one year, I look up and there's Jimmy Drana. I think it was the first time I ever laid eyes on you. I said, what are you doing? You're not the type of guy that should be walking around this whole thing.

23:06I just want to but I do want to talk about your persona Can I tell you whose fault that is? That was Richard Deitch's fault and I'll tell you why It always comes back to Deitch Everything you said there was accurate and then when Deitch left in 2018 when he left Sports Illustrated for The Athletic the bosses at Sports Illustrated came to me and said they wanted me to do more hardcore sports media coverage because I was taking over the podcast and his column was going away. So, and that wasn't a problem for me. I had no, because I love sports media. I'm all, I love, I can talk about the announcers and the broadcasters and scheduling and all that stuff.

23:48So I was, I was honored and, and thrilled that they asked me to do that. And that's why then I started attending those events and getting out there a little more. Is that a good answer for you? Am I forgiven or what do you think? Oh, you know, you're forgiven because you still maintained this sort of like, you know, every man bit, but you sort of got out there a little bit more to a way that really did surprise me. But I do want to talk about like how that, because if you're writing five days a week as the every, it's hard to maintain that, you know, hey, I'm just a guy watching sports on TV and let me write about it.

24:32How were you able to maintain that? Because I think that there have been subtle changes from when you started to where you ended, but you still have been able to maintain that persona, I think, in a pretty cool way. I appreciate that. I'll tell you what the trickiest part is by far and away. And you know this as well as anyone in this business. If you write a column torching an announcer or torching a broadcast or torching a network, you get page views, no problem, traffic, attention, engagement, all that stuff. It's not difficult. Number one, I never wanted to do that, even in the hot clicks days.

25:13And I always said to my bosses, I can't just do bash, bash, bash. I got to mix. There are plenty of things I don't like. I got to mix in what I like and what I don't like. It's got to be a balance. But in terms of writing negatively about people or networks or broadcasts, I then have to turn around and book these people on a podcast. So just an example, I've written and said many, many, many times that I think Sean McDonough is the best college football play by play guy in the business. And I think Sean McDonough should be ESPN's lead play-by-play guy. And I'm not a huge Chris Fowler play-by-play college football fan.

25:55I think he's phenomenal on tennis. It just doesn't resonate with me on college football. So if I write that and I say it on my podcast, it's very hard then to call Chris Fowler and say, can you come on the podcast? That was the tightrope that I had a walk that was extremely difficult. in terms of staying sort of as like joe fan that was never difficult to maintain because sports illustrated never tried to change me from that way so when i would you know bitch and complain about streaming all the time no one ever said don't do like that was how i felt like i wasn't i never lied i never made up stuff if any complaint i had was legitimate and i think you know you listen you hate talking about yourself like this you just end up sounding like a jerk but i i think i i maintained my authenticity throughout my entire tenure at sports illustrator i think that's what the key was all right so uh i'm gonna ask you a question and the answer to this question is going to be the rise of social media and the rise of uh of video like you like you like you talked about but so i i don't want to go to that sort of like obvious area because, of course, you know, from when you started in 2007 to right now in 2026, how has your writing changed or opinions changed?

27:19What's different about you beyond the obvious differences that we see every day in media? Well, I will say, you know, the older you get, I tried to be a little more careful in how I would rip people because these are people who have here. I never, this is the honest to God's truth. I never really thought any networks or executives were ever reading me or listening to me. I never knew that. I never thought it. And it would be Martian and Deitch who would say to me, oh, you know, this executive said this, or this person said this. And I'm like, why are they paying attention to me? Who the hell's paying?

27:57Like, why are those people paying attention to me i thought i gotta interrupt you for a quick second give me give me the story when was the first time you realized like my goodness sean mcmanus the head of a cbs sports that might might read me well i remember someone someone had told me someone had told me that bob costas was ripping me to them and said something like sports illustrated used to have this great media writer richard deitch and now they have this guy jimmy train he's terrible um because i would write negatively about bob so and i was like wait but like if you but if you would have said here's a million dollars do you think bob costas knows who you are my answer would have been no every time and i always like to say what was this what would the 10 year old jimmy train i think if like he knew that bob costas was taking shots at him well i mean listen i you know this is going to be inside new york here but obviously growing up in new york i listened to mike and the mad dog every single day of my life if you follow me you know that i have this sick obsession with mad dog i think he's so entertaining and you know now the nation has come to see him on first take but a couple of years ago i went to a 65th birthday party that was the biggest trip for me mentally that I've probably experienced in this, you know.

29:24But even so, like even last week when I announced my resignations, like the people who called and texted, I was just blown away, blown away. Because, again, like I don't – I'm still of the belief that, like, when I tape my podcast, I swear to God this is the truth. Maybe it's changed in the last maybe two years. But up until two years ago, I would go into it when I hit record, I don't think anybody's listening. Like maybe like six people who enjoy my work listening. Like I would see the numbers, but like I would never think that people in the business are listening. So I tried to be more. Listen, if I didn't like someone, I didn't like someone's work.

30:02For instance, when Netflix did opening day, I mean, I destroyed them in a column. Now, in the back of my head, I'm like, well, you know, I have to get a guest from Netflix on the podcast. That can be tough, but I can't let that stop me. I've got to. And I didn't make it. you know you see so much viciousness on social media i i try not to be vicious i try to just critique the performance um and that was probably the last one where i really went to town ripping and people like someone from apple was like very upset that i called the netflix broadcast an embarrassment i'm like well it was an embarrassment so i don't know what to tell you like wait somebody you know people working hard by that like this one of the sideline reporters that does the apple tv friday night game that nobody in america ever watches um was very upset because i said the netflix opening night telecast yankees giants was an embarrassment she's like people work hard there's produce i'm like okay well i'm not saying they don't work hard it's an embarrassment i i have found jimmy that if you're if you're critical and you're honest uh people respect that and that, you know, people will want to come on and people will want to come on and try to change your view of things.

31:24It might not make it easier, but you certainly don't put up a wall, you know, where they ignore you on that. I hate doing this. So if you don't want me to do it, I can't give you all the details. I can give you some details. I hate when people do that. But there is someone who I probably, there was someone that I have taken shots at a lot over the years for a long time. And that person reached out to me last year and wanted to have like a zoom meeting and went into like big fan of the podcast, listened to the podcast. I don't know if I quite buy it. And again, just like, I'm like, why did, why would you care?