The Press Box - Bill Simmons on Podcasting, Writing, Doing TV, and Being a Fan

Episode Date: May 27, 2022

Bryan is joined by Bill Simmons to discuss his journey in podcasting, his writing career, favorite moments, and what he sees next for media. Hosts: Bryan Curtis Guest: Bill Simmons Associate Producer: Stefan Anderson Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hi, I'm Derek Thompson. The news cycle these days is absolute madness. Pandemic, inflation, war, crypto, it's too much. That's why my podcast, Plain English, breaks down the news twice a week to be simple, memorable, and when it's appropriate, fun. No blather, no fluff, just the world's most important stories with fresh context and takeaways you'll actually remember. Listen to plain English free on Spotify. Hello, media consumers. Welcome to the press box. Brian Curtis of The Ringer here along with producer Stefan Anderson.

Today's guest is, wait for it, Bill Simmons. Between Grantland and the Ringer, I've been working for Bill for 11 years now. And trust me, we have had one hell of a free-flowing discussion about the media business during that time. But I wanted to bring Bill on for a big press box interview. Because I found I had a bunch of questions about his career that I never got around to asking him. Such as, why did Bill decide to start a business? podcast 15 years ago this month. Does Bill want to write columns again or maybe do a TV show? And with the Celtics rolling through the playoffs, how is Bill's idea of being a sports fan

changed through the years? What can I say other than Kyle? Turn the camera on. Here's Bill Simmons. All right, Bill, game six of the Eastern Conference finals is tonight. How does your excitement level for a possible Celtics title at age 52 compared to what your excitement level was, Was it age 17 or 18? Oh, come on. Age 16 was the 86 finals, and that was like life or death. The 84, 85, 86, 87.

I think sports means more when you're a kid. You've got less going on. So if it's a scale of 1 to 10, can you still get to a 9 or 9 and a half? Yeah. Yeah, I would say like 8.5, 9. It's really fun to go with my dad. I mean, we went to, I think we went,

I think we went to five of these playoff games and just, you know, he's had tickets for 49 years. So just that element of it is just, that's the piece that pushes it over the top for me. It's also a really likable team. And I thought Riscilla said something interesting in the podcast we did. Can't remember, maybe it was last weekend when he was talking about like kind of the DNA of crowds that have been there a bunch of times. And like when that game three I went to, yeah, it was last week when he said it about how there was no reason for the Celtic fans to think that they, had any chance in that game. It was like nobody could make a shot.

It was banged up. And yet there is smart goes out. And then Tatum goes out at one point. And yet when you've been to enough of those and you've seen the team come back, you just have this irrational confidence that it's always going to work out. So, you know, I think it's really special when you have the franchises that have been around for generations. Because I do think the building feels a little different in the big games.

And you've got this mix of people like my dad. and then people like me and then people who are like maybe teenagers are in their 20s who the team's kind of been passed down to them and I think for basketball there's only a few franchises really like that.

You know, I think the Knicks are obviously like that but they're never in the moment. I think the Laker fans to their credit to that franchise they've been like that really since the 60s and that's another team that's really passed down

you know, the legacy of the titles and the appearance. and the stars and all that. So you can feel it when you're in the building, I think. Your thing was always, I'm a fan. Yeah. Has your fandom changed in a significant way over the years? Just only getting older and just having less in common with the people I'm watching

and feeling like kind of the older guy. But it's definitely not a case of, you and I have talked about this when some of the sports writers that stay in it and they become, I forget what I used to call them, the middle-aged grumpy white guys or whatever when I was in my 20s and 30s used to make fun on them all the time. But I think there comes a time when you're covering the league that you could hit a danger point when you just don't have anything in common with the people you're covering. And they're looking at you suspiciously and they're looking at you like, you know, first

of all, you're from a different generation. Maybe you don't have the same background as they do and things like that. And you could see some people like kind of turn, people that used to the love of sports. Sports will come out in their writing and then it would gradually shift as the years went on. I think some people have kept it. Like Bob Ryan, he's in his 70s and I still feel like he loves sports. You know, and those were always the role models to me, like people like him in Gammons that truly love the sports they were covering. During the Celtics Buck series, you were in Boston for Game 5.

Marcus Smart gets his shot blocked at the end of the game by Drew Holiday. And people posted these photos of the play on Twitter because they could see you in the background. reacting. What does it like to watch a game knowing that you are being watched? I don't know. I didn't even know about that because I'm not a big like dive into the replies, but my kid, what are my kids do about that by my son? I don't know why, but somehow he saw it. It was like, hey, there's a picture of you. And it was just weird. I'm just standing there. But yeah, I don't know. I think when you go from being anonymous to being a little bit of a public figure, like it's always weird you know you there there's some sort of invisible hump that happens for me

um i was i stayed pretty anonymous until probably i started doing the tv at espn in the early 2010s and that that that was when i felt like a shift and it still feels you know it doesn't feel normal but it's also just it is what it is you know i still feel like um i'm still the person who was bartending in the 90s and would have dreamed of any anybody recognizing me, you know. So it's totally fine. But you have to worry like, yeah, maybe don't pick your nose. Like somebody might be taking a photo, stuff like that.

Don't even scratch your nose because it could look like a nose pick. It would be like the Seinfeld episode. This month is the 15th anniversary of your podcast. First episode's May 8th, 2007. What made you want to do a podcast in 2007? Just seeing on ESPN.com, Mark Stein, I think it was Mark Stein. It might have been Chad Ford's.

One of them interviewed Danny Age. And it was right before the Celtics draft. And it was like you clicked a button and all of a sudden there was an audio interview playing. And I'm like, what the hell is this? So I just asked for one. Like I was like, can I have this? What is this? And they were like, yeah.

And they sent me some equipment. And, you know, I looked at it as a tool that I could talk to people. you know, my friends, Adam Carolla, and maybe interview some people, but always like just a fun thing to try out. I certainly never expected where we go. I don't really think I saw that until about 2009. When people started asking to come on,

that was one thing. I remember Seth Myers pretty early. It was like, hey, I want to come on. And I'm like, really? You're listening? Like, I was just like dumbfounded by that. And then I think around, I can't remember when,

maybe around 2009, podcast to serious. And there was some serious channel and they announced a deal. And I was the headliner and the deal that my podcast. And I was like, wait a second. You guys are this is now something we're making money from. Let's let's talk about this. So that was right around when I knew.

I didn't really fully know the effects until 2010 because that's when people started mentioning it to me, like just people I'd run into. Because normally it would always be like, I love to call them in. And then all of a sudden there would be people who'd be like, hey man love the podcast i'm like really like i was always surprised by that but i think by oh nine 2010 kind of understood this was a really fun other thing to be doing i never thought it would replace writing for me but ultimately it did who gave the pot its initial title i of the sports guy oh my god i i think i i think i'd um i might have cold called with the with the readers of a mailbag

and asked them to send me suggestions and for some reason pick that one, which is one of the worst titles of all time, and quickly realized it. And we changed, did another thing and did the backup, the BS report. And I thought the BS report was a really good title. I was actually proud of that one.

And that just became the title. But not great, not a great moment. It's kind of the wrong body part. Yeah. It's either voice of the sports guy, mouth of the sports guy, or ear of the sports guy. I think it was a playoff of,

What was that show, the Queer Eye Show? What was that called? Oh, wow. I really think it was like kind of a play off that, like an I thing. Just because it felt like it had kind of a ring to it. And yeah, it just did not make sense. I should just call it the Sports Guy podcast. Like we know now that we've, you know, we've had Grantland and now the ringer, like,

don't really overthink the titles, you know? Like yours is the press box is a good, it's an example of like a title that kind of tells so the podcast is about. But for the most part, if, you know, Ryan Rusillo podcast should be called the Ryan Roussela podcast. Sometimes you can get a little creative with, like, Derek Thompson.

Instead of just calling it Derek Thompson podcast, you do the title with the host. Same thing for the town with Matt Bellany. So sometimes it's fun in the title if you can have the title and the host or sometimes you just go with the host. It's what you did on the podcast, a reaction to the way sports were talked about on ESPN or on sports radio during that period?

Yeah, the biggest thing for me, once I really started to think about it, was the Cousin Sal thing that me and him did. So when I thought about it initially, it was like, what are the conversations I'm not hearing? And sports radio at that point was really terrible. I think everybody was disenchanted with it. And you think like the biggest radio host at the time was Jim Rome, which should tell you where we were.

I'll do respect to him, but it was a certain kind of like semi-abrasive, big takes, come on in, what's your take? And I had always revered Mike and the Mad Dog. I just thought that was by far the best show I'd ever heard and never understood why that model didn't work in Boston. So that was in the back of my head, like Mike and the Mad Dog, what makes that show work? It's like the chemistry of those guys. So one of my goals, at least when I was starting, was I want to have people on that I've

chemistry with. And for me, those people mostly were my friends. So Sal and I, when we worked at Jimmy Kimmel show, he, we used to do Guess the Lines. We would go on Mondays. We would have, we were working together in 2000, in time for like the last month of the 2002 season in the playoffs. And he would be like, all right, Simmons, let's do Guess the lines. And because we sat next to each other. Our desks were next to each other. And he used to fuck with me all the time. But he would tell me, you know, all right, Sunday, one o'clock, and I would try to guess the line. He'd write it down.

He'd already made his guesses. And then we would see who won. And we would bet on it. And so after I left the show, this is weird, but we kept doing it on Sunday nights. And he would call me and we would guess the lines. It's like, no podcast. There's just a phone call. And we would play guest the lines.

And I think I even, I bet it's in my archives in like 05, 07 range, talking about sports talk where I was like, I don't understand why there's not stuff like when me and Sal do gets the lines and explain what gets like, I guarantee you can find it in one of those columns. So when I had the pot, I was like, well, I know I'm going to do this. On Sunday, on Mondays, I'll do guest the lines with sell. And then I'll call my buddy Jacko because he's really funny. And we'll talk about the Yankees and the Red Sox because at the time people really cared about

baseball. So 2007, the Red Sox won that year. So I know I'd do that. And then it was, I know I could talk to, I knew Mark Stein at that point. I knew Rick Buecker. I was friends with Steve Kerr. Mike Lombardi got bounced by the Raiders, so I started having him on.

So I really wanted to have regulars that I could come on, and it would be like conversations we would have on the phone anyway. And that's how it started. And eventually started getting guests just because there were so few podcasts back then, these PR people would just offer us guests. And it took me, I would say, about a year to realize what kind of guests to have. I remember I had a terrible podcast with Tony Stewart. that was just

I didn't know anything about NASCAR I got it I got his uniform number wrong to start because I just quickly researched him and he wore number 33 or his car had number 33 so I was like oh

we both have a 33 in common but it turned out that was like a specialty car but his real number was something else so it just got off to the worst start ever there's another time

I talked to Alton from the Real World Challenge Real World Road Road Road Road Challenge who was like the best guy at that time. And he was on his cell phone. And during the interview, he stopped and bought cigarettes on the pot. You can go hear it. I think it's on YouTube. And he's like, hold on a second. He's like, can I get a pack of cool? I'm like, are you buying cigarettes right now? So that

was where we were in the early days. The audio was terrible. ESPN compressed all the files. They sound, it just sounds terrible. But by, I would say, 08 range, it started to get momentum. And then when Obama wanted to come on, that was when I knew, oh, this is, this is actually maybe becoming something. I should try to plant my flag on this. Other than Tony Stewart and Alton, what just didn't work as a podcast in those early days? I honestly, it wasn't much different than it is now. You'd have like Rick Beaker on and you'd talk about, you know, who's going to make same,

kind of thing. It's like, how do I, what was a much different than when I was on my own with my, with my column in the 90s, just being like, I have to give people a reason to come here. There's no reason for them to come here. I'm on my own. I'm on this island over here. So I have to make the columns and pieces as interesting and unique as possible. They're not going to come.

And same thing with the podcast. It's like I want to stand out from these talk radio things, talk about things I like, and just kind of do it that way. So I would say it took me probably like two years to kind of understand the nuances of interviewing people. And one thing I learned pretty quickly was it was better in person. So around 2009, I started having people come over. And I had a bunch of people just come to my house, including, I remember Michael Eisner

came once. The guy who created Lost, he came, Jason Sudecas, Seth Myers, Bill Hader. Like, all these people would just come over. And I would just give them my address. They would come. We would do it two mics. And then they would leave. So when I started to figure out Grantland in 2010,

I knew the podcasts were going to be a part of it and had talked to Jacoby a lot about that, Dave Jacoby, and we really wanted to blow out the podcast. And I remember we were looking at Space and Naila Live for studios and could we make these live shows? And it ended up being this converted electrical closet that you've been in. But we knew. We knew this should be, we were way ahead of the game on it,

that we should have video. And I remember, I swear this isn't a lot. Jacoby can vouch. I really want to do this sponsorship thing in cars where I interviewed people for the pod in cars and then we would cut them out and they could be sponsored segments on SportsCenter.

And we were going to get it with Escalade. And it almost happened. We actually did a test drive once where we took, I think like an escalate to Vegas and we did stuff in the car. But we really tried to figure this out and trick it out. And then ESPN of course screwed it up. and we ended up not having it.

And then we just, the idea kind of fell away. And then Corden started doing the comedians with cars years later. And Jacoby and I were like, wait, this worked. This could have had, this could have been us.

Like we were so bummed out. Jerry Seinfeld. Oh, yeah. We were, we had it. We had it all tricked out. We had mocks. We wanted to do like big cars,

like a six seat escalate or something like that. And I mean, it probably would have been a terrible idea, which is the funny thing. Because I just sort of been driving around L.A. with like Lamar Odom and an escalated. It would have been super weird. I want to hear that podcast.

Yeah. But that was the other thing when the players started to come on. I think that really helped the podcast, too, just getting a combination of like regulars. People are really smart. But then you look back at all the people we had in the first five years. And a lot of them went on to like real media careers, you know, like Wilds and Jacoby and Mike Lombardi. Matthew Barry used to come on a lot.

then he ended up, you know, he became the biggest fantasy podcast and stuff like that. So we had some good people passing through. I think the first four guests, if I'm reading the internet correctly, were Mark Stein, Adam Carolla, Paul Shirley, and Marv Albert. Yeah, think about that. What a weird for some. Marv Albert was really good. I remember Walton came on pretty early and that one was good.

Yeah, I think the best part, the early years was, every time somebody came on, it was like the first time that'd ever been on a podcast. So like Jeff Ross, I remember he came over, the comedian, and he'd never been on a podcast before.

And we talked for like an hour and a half. And it was like right after Sal had tricked him, he had been, he was getting kicked off dancing with the stars, but Sal had texted him, he was safe. So Jeff Ross came on and tell that story. But we went for like an hour and a half

and he was like, that was amazing. That was so much fun. It felt like we were having lunch together. That was always my goal. is like make it feel like we were hanging out. I never used notes for it. I always tried to wing it without notes.

I would try to prepare beforehand and just kind of remember a basic structure of what we were talking about but not actually have notes so it could be more conversational. And then when we built the Grantland Studio, that was a big piece of it. We wanted the tables

where you could just look across from people. There was no crew in there. And I think that's where we had some of the best ones because it was so intimate. They forgot they were being filmed and recorded. So then we went to the ringer. It was the same thing. We did a lot of it in my office and tried to just make people feel like they are hanging out

with me versus appearing on something. I remember when the ringer started in 2016, you insisted that everybody come to the office. Yeah. There were almost no phoners, especially with actors, celebrity types. You wanted them in your office there. Yeah, that was, we didn't do phoners with celebrities by the time ago. to the ringer. We, um, I just feel, we also had more cloud at that point because, you know, by the, when we launched a ringer and my pod was, became one of the biggest ones. So that was,

um, that was good clout with the PR people. They knew it was like they look around. I'm like, oh, we should do that one. But it's just a way better experience, you know, and, and you can click with the guests on a totally different level. So we, we had some good ones. When, before we even had the ring, we didn't have the ringer office for, I'd say six months. So I had people coming to my house when I relaunched in October. So that was the same thing.

Michael B. Jordan, David Docoving, all these people were just coming to my house to do the pod. I remember Andy Greenwald and Chris Ryan were doing the watch for the first couple months in my guest house.

They would just come over like they lived there. And they would just do it with tape. I found the review that Awful Announcing wrote about the first podcast episode in 2007. Oh my God. I didn't even know this existed.

This is an artifact. Quote, if you're wanting this podcast to take off, wouldn't you do something a little different than rehashing all of your NBA columns with Mark Stein for 23 minutes? Wow. Little did they know, 23 minutes would become two hours of rehashing NBA takes.

You know, I was really wary of that the first couple years. That was probably the biggest issue with the pods was, I was still writing 6,000-word columns two, three times a week. And it was really tough to find the balance of, all right, what's this podcast versus the column? Because I ultimately wanted people to like both. So eventually that was when I settled on, bring the guest on, have them have most of the takes and react to their takes versus being like,

here are my thoughts on the Celtics that you just read 12 hours ago on ESPN. And I think eventually what you realized by the time I got to Grantland was there's two different audiences. I think the overlap of people who read the column versus people that listen to the podcast. I'm sure there was an overlap, but I think some people just like the podcast. They're like listening to it when they were working out or whatever.

Maybe they didn't read the column. So that became less blurry, I think, as the years went on. Two different audiences. And I also think the podcast at some point becomes a better and more efficient way to react to certain things. Well, especially in the Twitter era because there's more nuanced in a column.

It's tough. Although lately now, there's this new like screenshot era where people just take like two sentences or a paragraph and they blow out a proportion, whatever they want for whatever agenda they has. And that that's, you know, it goes back to the basic premise of the worst thing about Twitter. I think the last 13 years or so is it just makes everybody who does this too self-conscious. You know, it's whether you're writing, your podcasting, whatever, you're constantly worried about something being pulled out of context and then people coming at you for 24 hours. I care less than most about it because I'm old and what the hell. We'd be done soon.

But I think for younger people, it's a thing that we talk about a lot, you know, behind the scenes about you want people to feel like they can have takes and say stuff. And, you know, as long as it's within the lines, like, that's part of what's fun to listen to and read. And if you're constantly self-conscious and self-editing, that becomes, I think, a threat. Right. Earlier this year, after the college football national championship game, Georgia wins, I was like, I'm going to get online, I'm going to read everything that was written about this.

Yeah. And I found a few really good columns that were written after the game. Then I started listening to the podcast that were recorded after the game, including by the people who had just filed a column and were recording a podcast in the wee hours. Podcasts were better. Yeah. It's just like in a way it's replaced the post. post-game column gamer, you can still do a really good one.

But it's almost like, I want to hear an hour of people sort of hashing this out, thinking a lot about what they just saw. But before we pour dirt on it, some people are still doing good versions of it. Like, I think Winhorse just had a couple this year that were just excellent. That came right after the game that weaved in like a story about the game, but with real information that I couldn't get anywhere, that I could have heard on a podcast, but it was also fun to read. part of me feels like writing's going to come back.

I've been telling you this. Like, I think writing has started to fade away as from an impact standpoint. And I feel like it might actually circle back now. And obviously, we still care about writing. We still have a website that I'm really proud of. But I'm talking more about, like, what you just said about sometimes the reaction podcast or like whatever, a weekly podcast or whatever, it just feels like, can reach more people than a traditional piece.

And I think that's a hard thing to reconcile with. But I still feel like stuff like the wind horse, some of the big picture features, like you look at some of the stuff we have on the ringer, somebody being able to put in a perspective, like the stuff like Ben Solac and Stephen Ruiz and Kevin Clark and Nora were doing during the football season and Caitlin, that was like really smart.

It made me smarter about football in a way that I'm not sure a podcast can serve the same purpose. So I think for a podcast, either it's like you're reacting right off the event or you're anticipating what's about to happen. Or it's just a really good interview with somebody that you learn stuff. You know, and or it's like these people that become your buddies where you just kind of want to be in their world for an hour, you know, whether it's male or female. It's like I love this reality show and these three people talk about the best. So I'm going to go hang out with them. So it's like you're just kind of choosing who to have.

hang out with. But I still feel like the writing, the thing that worries me is that there's less and less unique writers these days, that there's a sameness to a lot of the angles and the copy that I just think if you go back 25 years, there was so many different. It was almost like wrestling. Everybody had like these different styles that were almost like their character. And I was, the thing I would say to you is like to cover the byline thing. If I cover the byline, would I know who this is. I think that's become harder and harder over the years to stand out as a unique voice when you're writing.

I'm a words guy, as you know, first and foremost. What's funny about podcasting me is there are moments when, you're right, if that Wynn horse writes that great column that has all this info in it, I definitely want that to exist. I don't want that to be replaced. But I look at a lot of them, and I think that would have been better as a podcast. I want that person in front of a microphone talking to me after the game about what they just saw. Yeah.

Rather than being fitting themselves into a newspaper, fitting themselves into whatever deadline they had to fit themselves into. I agree. Right after a huge game. We did something. My dad and I did something after game four because, you know, we would always leave the game and just walk home and talk about the game. And I was like, Dad, we'll walk back to your place and we'll just immediately record a pod like we would if we were just talking about the games. I was like, I don't know. It's late.

I'm like, come on. you got this. So he had like a Coke or ginger ale who's, he was ready to go. It sounded like you were keeping him away. Yeah, it was, it was like 11.30 his time,

he's 74. So I think that ginger ale helped. But it was basically a conversation we would have had anyway. And I was like, this is cool. I'm glad we did it this way because we just went to the game. We saw all these things. And we're just going to basically word dump it on you.

But I thought that was fun. I think some of the stuff, you know, I've tried to change my pot during the playoffs. to come on Sunday night, Tuesday night, Thursday night, which does it like delight my wife. But I think sometimes you got to be more in the mix. Like the way we did guest lines,

me and Sal for ever was Mondays, right? And it would go up Monday like 4 o'clock ET or maybe sometimes even later than that. And as the years passed, things just moved too fast. We'd start taping on Sunday nights. People want to know right away what you thought. You got to have good angles. And that's where like I think,

putting in the work and having some natural talent and some sense of history for it, too, I think becomes advantages. Because if you're reacting right away, that's, that's hard. Like, you have to, like, figure out immediately what were the biggest angles. How are we going to hit this? How are we going to hit that? Do I have a take? It's just hard.

It's like speed chess, but it's hard in a fun way because I love it. There are basically two types of sports podcasts now. The first type is I am interviewing a famous person. Yeah. And the second type is I'm hanging with my friends. Yep. Do you find yourself gravitating more toward the interview or the hang? The hang.

Not just hang with friends, but hanging with people who have expertise. You know, I think that part's the interview stuff. I still do them. I'm definitely doing less than less than I did in the 16, 17, 18, 18, 18. 18 range have been picking my spots more with that because there's just so many podcasts now. It feels like just everybody's being interviewed all the time. You know, so there are these eternal podcast guests that are just going. It's like Charles Nelson Riley used to be on the late night shows, you know, just go from

couch to couch to couch. Yeah. Or if they're promoting something, I remember I had Ed Norton on and I was really excited because I really like him and I like his work. And he must have done like 12 podcasts. So I was like one of the 12. And that was, I had this small moment. where I was like, all right, that's, I don't know how special that is for a listener.

If he's on, no offense to Ed, by the way, he's promoting, or I should call him Edward because he wants to be called Edward, but he's promoting a movie and he wants to get the word out in as many ways as possible. But I think over the years you kind of learn maybe you don't want to be one of the 10, you know, so I try to veer toward what can stand out a little bit more. You wrote on Instagram the other day that you've never gotten David Letterman on the pod for an interview? Yeah.

Who else is on your list of interviews you want before to do someday before it's all over? That's definitely the biggest one. I think Eddie Murphy would be interesting, but I don't know how much he'd say. I've interviewed most of the people I've wanted to interview, which I think is weird. But just like the ones, if I made my bucket list in 2009, I think I've gotten a lot of them. there's um there's some that just would never happen there's probably some definitely some musicians that i think would be cool um but for the most part i it's like letterman would be the ultimate one mhm jack nicholson is he on the list would have been on the list

in he would have i think he's too old though i don't i don't know what what kind of uh what kind of shapey is then there's people like leo would be amazing but i don't think he would say anything you know scorsese would be amazing That's Korsese would definitely be on the list. But I would gravitate more toward people who haven't done a lot of stuff, you know, because I think that's when it gets a little different. But we had a run with the ringer the first couple years where there was one year where it was just it felt like every week somebody cool was coming in.

It was like Kurt Russell, Jeff Bridges, you know, Greta Gerwig. And it's just over and over again. And that was really fun. But now there's so many podcasts that just feel. like it's less special for the guests maybe than it used to be. Now it just feels like it's like the new version of a late night talk show. You know, where it's like I'm doing this and then I got to do this and in like four podcasts are a piece of it.

But I still feel like I can get something interesting out of whoever. I remember the early days the ringer because you were marching people through the office. Yep. It was fascinating. And one time I think it was Bill Hater. You had him on and then you had to go do something. So you sort of just dropped him off in my office. office. And I was sitting there. He just started telling stories and you can hear, I just feel

everybody in the offices around me, just listening in. Yeah. And being like, oh, my God. And then you came back and you're like, all right, he's like, all right, Brian, nice to meet you, just see you later. And I was like, that was an incredible 20 minutes. I just fit with him. It was, it's pretty weird when, you know, we create this workspace and then all of a sudden, like, Jake Joan Hall is walking through it. I think, I don't think that ever didn't seem weird to all of us, you know, especially to where I was doing my pod just to watch somebody kind of walk through and see like, oh, there's Gucci Main, just kind of strolling through the courtyard. I don't think I was there that day.

Yeah, but yeah, it's definitely a fun element. I really missed it. You know, during the pandemic, I definitely did less guest interviews than normal because I just on the Zoom it wasn't the same. You can get like 70, 80% there, but not 100, in person. and it's just 100% better. Was there any NBA player who you never got? I think I got almost everybody.

Trying to think going back. Kobe, we got on Grantland Basket Hour. I never got LeBron on a podcast, but I feel like we did stuff. And he came on the countdown set after game seven in the 2013 finals, which was like one of the most fun interviews I've been a part of because he just won

and he had a lot of champagne. I guess Westbrook, no. But I don't know. think he would say anything. James Harden, I don't, I don't think he would be that interesting. There's a new wave of guys that I think would be fun. But now we're in this new era of Draymond Greens. It's like wrestling.

Draymond Green's calling them the new media. The old media's out. It's just players interviewing players. That's where we're headed. Yeah. Podcast or Draymond Green. Yeah. I don't, the new media, I think, will be essential, but I don't think it's going to replace

anything. I think it will be additive. I hope. we do a feature here at the press box called Instant Think Piece or Half-Ass Think Piece. I'm going to give you one here. As a writer, your corner was always, I actually love sports. Yeah. I actually love watching games.

Some people might not or might seem like they don't, but I do. I feel like the podcast era has pushed people even farther in that direction. With a whole vibe of every podcast, whether it's about sports or pop culture or the Marvel universe or whatever is I am a nerdy enthusiast who loves the thing I am talking to you about. Yep. And on this podcast, we are going to nerd out and love it together. What do you think about that? I think it's been less in sports and more in pop culture.

But I think Marvel has been a really good example of that. Van won't mind me talking about this because I've talked to him about how far do you go on that on the ringerverse podcast, which I think we have the best nerd culture podcast. I'm biased, but I really do think we have the best one. I don't think it's debatable. But if they don't like a Marvel movie, it's okay to not like the Marvel movie and talk about that on the podcast. My stance is, yeah, you lose credibility with your audience if you're going to pretend

something's good when it wasn't. And I, and look, I'm not a huge nerd culture guy, but I follow it. And obviously, you know, being. being in charge of the ringer, like we've really dipped into that stuff. The stuff hasn't made good the last couple years with the exceptions of like Mandalorian. I think the Spider-Man movie was a big hit,

but I think people have been hesitant and just feel like that wasn't that good. And I feel like that's going to swing around because ultimately authenticity is the number one advantage you have in a podcast. And there's no way to hide. The listener can tell. And that's why I think some people have been better at it than others.

And I think that's why some podcasts have become bigger than others because you have to have the authenticity. It's too hard to hide when you're talking to somebody for an hour. You are who you are. You're not, nobody's that good of an actor. If you're that good of an actor, you'd be acting. You start the podcast in 2007. When does ESPN start caring about the podcast?

When they did that serious deal, when I was like, I'm not, this isn't part of my contract, I'm not going to do it anymore. and they're like, oh, well, here's some money. And I was like, oh, you guys care about pie? But they never really cared. I mean, and look, you could go back and read a lot of the stories, especially from the last couple years when I started really struggling with them. A lot of those struggles had to do with the fact that they weren't monetizing the podcast

and that they gave it away. And I said that on the record, which maybe wasn't a great strategy idea in retrospect. But, you know, at the time, the last 18 months of Grantland, like, we wanted to grow. We had this amazing, you know, content factory that we had and we had found all this talent. And I really thought we stood out in a special way. And anyone's reaction when they have an asset like that would be to, all right, well, how can we make this better? And ESPN's their attitude at the time was, you have enough headcount. You're good. And I was like, we're not good. We have 10 podcasts. We have one podcast producer, you know.

And like, that's insane. And we have, we're doing video. We have two video people total. And we need to have more people. We need social and all the stuff. They just didn't get it. They gave away. I still feel like they're giving away now.

You know, I'll do respect to the people running it because it's not the same people that were running it when I was there. But I don't think they leverage it financially like, like they could. But back when we were doing it, we had nine of the top 10 podcasts at ESPN. and they just threw my pod and all the Grant Land pods into their subway deal.

Like we were like a free set of tires, you know, and then they would earmark whatever fake figure. So it was like for us, it was like $650,000 for the year is what you make from podcasts, something like that. I have all the numbers.

And I'm talking to Coral and Coral's making way more than that. And I'm just like, what's going on here? You're telling me we don't have the money to hire stuff. you're selling our pots for 10% with their worth. And it was just really frustrating because we, you were there. I felt like our staff was, everybody was grinding in a way that I don't think we got credit for.

And at some point it's not sustainable. And I was really wary of like, is this sustainable? Are we going to burn people out? Can we continue to be this good if we are doing this with less people than we should have? So I have no regrets about that. You have another anniversary this month, another career anniversary.

It's the 25th anniversary of your first Boston sports guy. Yeah, that already happened, I think. Yeah. May 20th, 1997. What do you remember about writing that first column? I just remember trying to get at launch for months on Digital City, Boston at the time. And I think it was about Tim Duncan. and it's probably terrible.

The big thing was the thing that got it going for me was the draft diary in 97, where the draft happened. I wrote down all these notes. I typed it up and put it up. And I think right afterwards, I had like 30 worst sports movies ever. It was a ranking.

And that one did well. And they put that on the AOL main page and got all these emails. I was like, oh, all right. And, you know, the goal for those first five years was just, or first four, whatever it was,

just write about stuff that my friends would read because I felt like I was in my mid-20s at that point and I just felt like nobody was talking to me in sports. They weren't talking about the stuff that me and my friends talked about. Now I think,

now we have an overload of everybody has somebody they can go to, right, for whatever you care about. You could even say like, all I care about is the Dallas Cowboys. How many places could you go for info about the Dallas Cowboys, right? in a dozen, two dozen, three dozen.

In 1997, a Twitter account. Yeah, I cared about Boston sports. We had the Globe, with the Harold, we had the Phoenix once a week, and we had this all sports radio station that wasn't good. And had a huge audience and thought they were good, even though they were. And that was all we had. So I was like, who's talking, the conversations that I have with my friends and the things we talk about, I don't see it.

So that became the goal. Do that become weird for you going from I'm the guy who's writing about the thing that was so specific that nobody else is writing about it? Yeah. To this whole army of people writing about the very specific thing that I'm slowly becoming a generalist

just because the way the media is changing around me. Yeah, what year are you talking about? Oh, I don't know. Next to the next two decades of American sports and pop culture? Well, the big, challenge was how do I write a column that can appeal to people that don't live in Boston? So that was like what I tried to figure out when I was going to ESPN. I think I took five weeks off and I spent most of that time just trying to sketch out ideas that I thought would work for

people. And what I realized was if I can flip out Boston sports for the most part and replace it with pop culture, keep some of the Boston sports, keep the fan thing and make that my angle. then I would have a chance to stand out because I didn't see anybody doing that. And then for, you know, pretty messy the first year, especially from, I definitely was writing way too many words and just trying to figure out where the lines were and stuff like that

and not being able to make fun of media members and then trying to figure out roundabout ways to have fun at their expense and things like that. But for the most part, I didn't really have a road map, know it's like the only national column was Rick Riley and he was writing 800 word once a week really targeted things and I knew I didn't want to do that so it was like how do I how can I get people my age and younger writing about the stuff that they care about so the pop culture became a big piece of that and I already had that anyway in the old site but I felt like that was

like once I figured that piece out then it became easier and then just you know writing from a fan's perspective from a perspective of somebody who love sports, I think was a huge advantage. I always thought, Mike and the Mad Dog were a good roadmap for that because they really love sports. That's why the show worked. It wasn't just like that they were doing it to do it. Like, they loved sports.

Mad Dog was a psychotic San Francisco Giants fan who would stay up late at night to watch the Giants games. And, you know, Mike was watching everything. And it just seemed like it was like everything they cared about was tied into the show, you know, and I thought that was pretty instructive. And then, you know, some writers like Roger Angel just out. I know he talked about him on the podcast, but the way that he kind of straddled that balance

was really, really formative. My style was nothing like his style, but a lot of the DNA of it, I think, was stolen from him. Because especially like AgnCord and Aftar and some of the fan kind of stuff that he wrote about, just really resonated with me. William Goldman was another one that did that.

And for the Boston Globe, LeMontfeld, Ray Fitzgerald, were two people that straddled that really well. early loop because same thing so there were people doing it but by that time i had the column in oh two it wasn't really out there as much and sports was very um it was very like you argued a side and then you just argued the hell out of it you know and that was kind of the column so it'd be like barry bonds is a bad guy now just be your column you just argued that side and you wouldn't have another side in the piece now it's the opposite thing that's the opposite thing that's the opposite thing And now everything is, even if you're arguing a side,

you're still trying to self-consciously bring in the other side, which, you know, in some ways, it's a better place to be. And the other hand, it was still fun when somebody would be like, I have this take, and here it is. I will hear no countertakes. So. You know what I miss it is during the F1 boom that we're in right now?

Because if it were 20 years ago, we'd have one of these crusty middle-aged guys. Oh, it would be amazing. You know what? Formula One is really boring. Yeah. There was one lead change at the race. This sucks.

Don't watch this anymore. Oh, my God. And I wouldn't even disagree. I wouldn't even agree with that take necessarily. But there was something kind of amazing about that take being out in the universe and watching people dive onto it and respond to it. Those takes should still be out there. Like somebody could have written a great conference finals piece about basketball sucks now. You watching this?

The threes and the nerds have ruined basketball. just written 1,200 words that the nerds ruined basketball and then people would have gotten mad and yeah, that stuff just doesn't happen anymore. I think, I remember, like, I had some Manning Brady stuff for ESPN where I just became convinced

that Brady was Russell and Manning was wilt and that he was just going to put up huge stats and never win a title. And if you go back and read some of these columns, like I'm just definitively saying like, Manning is a loser. He will never win. You can never do that now.

I'm kind of glad those comments. exist though because you know I think there was something fun about that area even though it was ridiculous and I'm sure I would take back half the stuff I wrote but you the whole point back then was pick an argument argue the fucking shit out of it and don't accept counter arguments and then I think I felt like my style the stuff like if I go back and read my old stuff I don't really feel like until about 2008 that I felt like I elevated like the kind of the the quality of what I was writing. And just in general,

I told you this back in the day, that late 30s is kind of when it all comes together as a writer, I think. You figured everything out. Yeah, and just like how to go a level up and how to continue to try to get to angles ahead of other people

and then write them in the most creative way possible. And I really, I loved it. I really enjoyed it. You mentioned the length of those early ESPN columns. Yeah. Is that you saying, I have 3,000 words in, inside me and I must get them out? Or are you trying to outflank Riley and all the guys in the

newspapers and say, I'm going to give you more than they're giving you in a column? No, that's a damage writer who wanted everything to happen a lot sooner than it did. And then when it finally happened, it was because I single-handly made it happen and nobody helped me. So then when I got to ESPN, I'm like, nobody's helping me. I've got here on my own. I will continue to be here on my own. And to my detriment, because I'd get editors. And I battled with some of them, especially in the early years. And I look back now and I think, like, if the person, if me now was trying to manage 2002 B, I would have not liked me.

Because it was super stubborn. You know, I'm like, don't tell me, don't take that out. You don't know better than I do. But honestly, it was damage because it was the only way I got there was to do everything myself. So you don't want to help at that point. So it took me a while. I had Neil Fine and ESPN the magazine was the first editor I kind of trusted. And I had to because in that case, initially it was like 670 words, which was, you know, insane.

Then it got to 800. And then where we landed when the column I think got really good was about, it was like about 1,200, 1220. And I would send him, I don't know, 1,400, 1380. And he'd have to cut 150. I just, for the first time, I was like, I trust this guy. I think he'll get the best piece out of this. And so think about that. That wasn't until like 2007, you know.

So that, to me, that's just like not knowing any better and not having the right role models. You like to joke about how your fingers stopped working? Yeah. Why did your finger stop working? It's because of Cornheuser. Cornhizer told me. He told me at 43 your fingers stopped working. That's what happened to me.

He just told me like it was like this horror movie play. that was going to happen. So right when I turned 43, I just, I started thinking about it. But I think for me, I just kind of said, I wrote everything I wanted to write for the most part, you know, and I didn't want to get in the habit of having to repeat myself. And the more I did it, the more I just felt like I was doing too many other things. And I didn't want it to be just one of the things I was doing because I really cared about it, you know?

and like, oh, it's Tuesday, I have to write this piece for three hours and then hand it in. And then I'll move on the next thing. Like, what we did with The Ringer was, you know, to start that from scratch and basically come up with every decision for it, along with a couple other people. Like, it was really fucking hard. You don't have time to follow things at the same level and spending the time that you would need to on writings. And I just felt like I wasn't going to do it unless I felt. 100% good about it. I came back after my show got canceled. I had like a year where I was writing and I felt good about it. And I thought I wrote a few good things where I felt like,

all right, if I, I could do this. I remember I wrote like an MVP column in 2017 and I handed that and I was like, yeah, I can still do this. But just to balance all the other stuff, it was too hard. I wish I could. For me, it was always like a, much longer process than I think people realized. I think some people can just bang it out in a couple hours. I would write too long. I would edit. I would go back.

I would change stuff. And I just, it was always hard for me to just crank stuff out. There's a couple times of my career when I realized, like, the way to do this is just to be writing every day. And a lot of times I just don't have the time. But like the first year at Grantland, I felt like I was in a really good groove that year.

because we were just right we had to. It was just all I was doing was doing words and writing and got to the point where I just felt like I could write anything in three hours. And I felt that way after I was doing my basketball book in 2008-09 when I was just, I had to get in the habit of writing because I'd finish it. And then it hit a point where I was like, I can write anything. I remember I spent, I did a trade deadline piece with Baron Davis

where I hung out with him for the trade deadline. And then I had to hand it in. they were delaying the magazine. They were basically saving the last page for me for the magazine. And it had to be in by like, I don't know, 5.30 my time. And I had to, I spent trade deadline with him in the Palisades. Finished at like one. And I drove back to where I lived, which was like probably a 40 minute drive.

So I was starting. I went to, I went to La Pancunditin, whatever that place is called. And I sat down at like 2 o'clock. Maybe it was like 2.30. And I had like two and a half hours to write 2,000 words, like good 2,000 words. And I just did it. And I handed it in like 445 and I just felt like I was like superhuman. I was like, yeah.

You know, that's what I probably missed the most about writing. It's like when you're just like you have no choice. It's got to be in. It's got to be good. So yeah. Once you can't do that as well, I think that's when that's when the wheels start coming up. So there's the deadline rush. But what else do you miss about writing?

I mean, I miss like the big moments when you get to weigh in in a real way after something happened. And people are kind of waiting on whatever your thoughts were for whatever reason if you have some sort of audience. And I remember the 04 World Series. I was writing a lot, like that whole playoff run. And I was really burned out. And I think like game four and game five were right back to back because there was a rain delay. So game three is a Saturday night. Game four was a Sunday.

Game five was a Monday. And that game four Sunday I went to the Patriots game. The Patriots had this winning streak. They beat Seattle. Came all the way back and went to the game four that night, which became the Robertsdale in that famous game. And that ended, I remember when that ended, probably around 1230, something like that. And so I knew I was going to write that day. My plan was to write after game five.

And I remember I was talking to John Papineck, who's the ESPN.com person that day. And I was like, I was like, I think I don't have anything left. Like, I don't think I'm going to write anything. Like, I think I'm just going to wait until after the series and I'll write, I'll write some big piece. and he was like, you can't. Like, we're going to lead the website with it. Like, we're around, he gave me this like Rocky 3 pep talk. It was like, you're leading the website.

People all around the world are reading these things. Like, this is what you always wanted. How do you not want to have a piece up after game five? Like, isn't this what you wanted your whole life? And I was like, you're right. So that night, they won that game again. And it was another amazing game. I think it was like 12 innings or 30.

13 innings. It was 25 innings in two days or 26. I don't remember. And they were celebrating after it came home. I got like this 64 ounce Coke or coffee or something from 7-11. I went back to my dad's house and I tried to finish the piece and I handed at like five in the morning. It's like probably still my favorite thing I've ever written because I was like the pitcher that had, I'd thrown like 180 pitches, but I had to get through the ninth inning. But I also like I'd just seen this amazing sporting event over the course of two days. I was like, I got to capture this. And, you know, in the best I possibly can.

So I was in a weirdly important day for me because he was right. It was like, this is what you always wanted. Like step up, suck it up. You got to do it. What's more satisfying? Recording a great podcast or writing a great piece. Oh, writing, writing wins every time. It's easier to have a good podcast than it is to be a good writer, I think.

Don't you agree? It's performance, I feel. Like, I performed well. My cue, the cues came to me. I got the words out of my mouth. I did it. I shut it down. Whereas writing is, as you described.

I wrote it and then I wrote it again and again and again and figured out what I wanted to say and honed it. And it's almost like sprint versus marathon. Yeah, if you're writing correctly, it's got to take something out of you. You don't finish a piece that you really slaved over and then you're like, okay, what's next? I'm going to go do that.

I'm going to go hit some tennis balls. Like, I would finish a piece, and I wouldn't be able to function for like 45 minutes, you know? And I just feel like if you're doing it correctly, you're absolutely painstakingly going over every sentence. Now, it's funny because my stuff was always too long. The irony of that was I was still painstakingly going over all the sentences. They're probably too long.

I definitely could have cut it. 25% of it in some cases. But I was, it always, to me was like how Jed Apatow's movies are too long. And he has, when he gets criticized for it, he's like, hey, that's just how I do it. Like, what's wrong with more content? So I'd always feel like, yeah, what's wrong with an 8,000 word mailbag? Now, I think what changed for the writing, I think, and you could feel it happened at Grantland was the phones.

And once people started reading on phones, the 8,000 word piece, I think, became a lot. harder to defend when people are just scrolling scrolling in their iPhone think about grantland we designed for desktops and then right the iPad showed up like what's that and then david show who's working for us at the time was trying to figure out to redesign that would look good on the iPad like yeah the iPad that's the future not even realizing that the phones would actually be the future so and then who knows what's what's next like visual visual uh like you you put on like 3D glasses and you just read a piano. Who knows?

Yeah. I'm reading a media column to you and your virtual reality set. I don't know. Andrew Marshand is a hologram of him is reading, reading me Tom Brady, $375 billion reports in my living room. He's just standing there? I don't know what's next.

Could be anything. Do you think you'll write regularly again? If I did, I would have to take like four or five months off and almost like going to a cave and try to do it. There's a couple ideas I've had that I'm just like, man, I wish I had time to write that. But I don't know. I feel like I've said this before,

but I feel like it's like golf. Like if you're not playing, you can't just be like, I'm going to go out on the course today and shoot a 68. Like you really have to put the time in. So for me it would be like a multi-month kind of, a kind of practice practice round.

But it's hard. We're up to a lot of stuff at the ringer and Spotify, obviously. So to just be like, hey, I'm going to now do this. I don't know how realistic it is. Semi-related question. Do you want to do TV again?

I don't know. I've had some chances, but I just think like I was never able The one fun thing that I did that really felt right was the Grantland Basketball Hour. And we only did 10 of those. But that was the only time, you know, it's weird because I was able to create my HBO show from scratch and just couldn't pull it off in the way that I think in my head, I thought, you know, be way more interview based. I mean, that's a whole other story.

But the Grandin basketball hour was like, this is really fun. I'm working with my friends. we're doing something that nobody can get anywhere else. Now it's like a lot of the stuff that we did on that show, I think, is in different shows now. I'm not saying like we created it, but we just, we had such an advantage back then because we were basically making it like the most awesome video podcast we could have and good production, things like that. But that was really fun.

I really like the situation we're just in now from a media standpoint with what we're doing. Like we could do the right once we have the now we have the studios back and the pandemic's over and we can do some video podcast stuff that people can watch on whatever device they want. So I must think that concept of do you want to do TV again. Like I feel like I'm doing TV anyway. You know, like if we once we're doing rewatchables in studios and you could just watch those on an app, is it really any different? So would I want to do the TV like the studio shows that I'm watching now? No. I wouldn't.

I already did that. It sucks. You know, I watch it. I watch it now and I watch like the pregame shows where they have four minutes to all get their takes off. And it's just like that wasn't fun. I already did that. Even if inside the NBA calls and says, come on and just like once a month and just troll Barclan check.

No, I just bring you out. I just wouldn't do it. I don't. I already did it. It wasn't that much fun. It's not the kind of. especially now what it's becoming where you got to come after a game

like Heat Celtics game five like Kyle Lowry should be banned from the NBA for how bad he was and you just got to like go completely over the top with you can't just be like wow the heater banged up maybe they shouldn't be there like where's the nuance

on shows like that they don't don't really exist I think the T&T show is spectacular but it's you can't compare that show to anything I think it's notable that no other show in any sport has been able to even come close to capturing it. It's because they have Barclay, who's the best ever in any sport, plus Kenny, who's the best sidekick ever. And then they even figure out how to work Shaq into it.

You know, and it's just the best. It will always be the best, and nobody should try to compete with it. In terms of talk shows, I wonder if we are at the end of the linear TV talk show we are. Oh, we definitely are. But, because I was just thinking this the other day, If you had to pick one person in sports, TV, print, radio, and give them a talk show right now

that would draw a lot of people. It wouldn't. Who, who, like, if I could give you anybody, would anybody work? Why would I do that over a podcast? The only thing that's been able to survive and is undefeatable as PTI with Coronerazer Wobahn.

But that's way before, that's grandfathered in. I know, but it's still, that's the only show, you need for those afternoon shows. That's it. They hit everything in 22 minutes. I think that show could evolve a little bit.

I wouldn't, you know, I wouldn't be opposed to them tweaking like the third act and stuff like that and the fourth act. But just in general, that show still has it figured out the best. I think first take's been really interesting in the mornings. You know, I thought when Stephen A got rid of Max Kellerman, I didn't understand that at all because I thought, I think Max is good. but now I understand what the thinking was where just to bring in different types of people and you make Stephen A. the star, but he's got, it's not much different than like a podcast, right?

He's just got different people that come into his orbit. And I think they've done a good job of selecting who he should kind of be battling with. I can't personally watch that show for longer than like 20 minutes, but I do like it. I respect it. I like it from like 7 o'clock to 7.20. I'll make coffee. I'll see what they talk about in the first segment. I really enjoy watching Steve a day on TV, which I wouldn't have said 15 years ago.

But I just, I just think he's good at what he does. And, you know, in terms of like what you're asking, like, I just think podcasts, if it's an interview show, why wouldn't I just watch a podcast? That's what I realized as I was doing the HBO show. It's like I'm having these guests on. And if they were, if this was a podcast, it would be better, you know, versus like an edited 10 minute segment of an interview. Like, I had Joe Rogan on in 2016, and we talked about UFC for 10 minutes. So would you rather heard that or have heard us talk for two hours, you know, on a whole bunch of things. Like, so you start thinking about stuff like that.

And I don't know. I just think it's going to be hard. The only like streaming talk show that I think still works for what it tries to do is the Marr show where like the structure of it, where he comes out, he tells jokes. he's got that one guess that's always really topical then he brings the two guests in that they battle about certain things he interrupts them constantly, whatever

and then he does the new rules at the end that they put time in and ends with the long monologue like the structure of that you would say from a sports show could that work? Yeah, like could Stephen A do that show the sports version of it except for the monologue probably

but I think he's better on first take reacting I think that's just a better use of them Yeah, and it's really helpful to be a professional comedian. Yeah, it's true. And that was the big thing I was missing, which is why I really tried to steer it around the interviews. But it was in 2006, that works. But in 2016, you have podcast now.

And it's like the interviews just don't feel as special. My first show had Ben Affleck and Charles Barkley. They were both great like that. I remember Ben Affleck. Who could forget. He was great. We had like 30 minutes. say him. We ended up using seven, but he was great the whole time. He was really, uh, energetic, I would

say. And Barclay was awesome too. And, uh, and it was turned out to be a 27-minute show. So, you know, I don't know. I don't know. I think Kim on Colbert and those guys will be the last wave of people that I, I heard Baloney say this when Gordon leaves, will CBS even replace that show? or will they just hand it over to the affiliates and just do reruns? That will be a test of where late nights going. If CBS looks at that and goes, it's not even worth it for us to replace him, then that will tell me we're probably headed toward the end.

And that podcast, podcasts have won. I got some all-time NBA media pantheons for you. Yeah. Is Bob Ryan first? Well, he's down the list. I'm naming a job. I'll give you the options.

who was the best ever at it. Great. Please throw in anybody I forgot. I'll probably get in trouble, but go. Here we go. All-time best NBA play-by-play announce. Marv Albert, Mike Green,

Dick Stockton, Johnny Most. Oh, Johnny Most. We love Johnny Most, but he was terrible. There'll be some funny ones in here. The fourth one is often going to be the fun of one. Anyway,

Best all time. I would go 80s, 90s, Mark, I think. I think, especially if you look at like early 90s, Mark, peak of his powers, the best. Breen is really good and an awesome guy, but I think even he would pick Mark.

Current best NBA play-by-play announcer. Mike Breen again, Kevin Harlan, Iron Eagle, Mark Jones. I would say Mike Breen. I still feel like Sean Brandy would be really good if he did it. He's the one I just don't understand why he's not on TV. But I think Mike Green just has, I think part of being a great announcer is the audience familiarity.

And when he gets more excited, I get more excited now. It's like the Al Michaels thing where I have this history with Mike Green. So if he's really, if he sounds more excited, then I get more excited because I know something great's happening. It's like the tone of voice when your friend calls. Yeah.

And you know immediately how it's, excited your friend is because you have that history. Exactly. I don't have that with Ion Eagle yet. I think Ion Eagle is really good. I don't have that Ryan Rico. I think Ryan Rucco is good. But, Breen, I just, it's just been enough of a body of work now that I think he's the crucial guy. All-time NBA color analyst.

This was tough to cobble together. Hubey Brown. No way. Jeff Van Gundy. Steve Kerr, Doug Collins. It's Steve Kerr, and it's not close. Why Steve Kerr? He was the best.

He was the best at it. Because he had just played. He had the right, he was also an unbelievably good podcast guest. He had the right sense of how far to push something, sense of the moment. There was real respect because he had won titles. And I think he's the best. I think Van Gundy can't be really good.

I wish it was just him and Breen. I think JJ has the change. to be potentially the best. From the stuff I heard from JJ doing games a few times, I thought he was awesome. I thought that was the best I've heard since Steve Kerr. The way he woven, what it was like to play against certain people and how he knows he's really analytically savvy,

spends real time on it, and wasn't afraid to have takes, which I think is a piece that we forget with that job, this. Don't be afraid to light somebody up every once in a while to do it. Van Gundy will do it sometimes, but he, Van Gundy's very hesitant to criticize coaches. JJ is not hesitant. So I think JJ has a chance to be as good as Kerr was. By the way, on that point, if I were TNT, I would go take JJ from ESPN and I would call that one in with Adam Silver. Ooh. Because we can't do. We like him for the number one slot. Yeah, we want to make JJ our number one game guy,

please help us get him. And maybe he could be on ESPN, but do games for T&T, whatever. But that's how good I thought he was. All-time NBA studio show host, Ernie Johnson, Bob Costas,

Pat O'Brien, or Sage Steele. Your deck. Ernie's the best at it. Certainly the most reps. The best thing about Ernie and a lot of other hosts could learn this, it's like just do the word count with him.

Keeps it moving. When they say he keeps it moving, part of the reason keeps it moving is because he doesn't have to do a 30-second soliloquy before he throws it to Charles. Sometimes they'll just be Charles. What do you think? Shaq? Sometimes it'll be a one-word transition.

His whole job, he wins if the show's good. He doesn't win if he's good. He wins if the show's good. And the hosts that realize that are the best hosts. ex-NBA player who should have been a bigger star on television. Will Chamberlain, Kevin McAil, Kobe Bryant, or Magic Johnson? Well, you have the two I would have picked Kobe and Mikhail.

There's an alternate universe where Mikhail is Berkeley. And instead, he became a GM and a coach and all that stuff. Kobe was amazing. doing the when jaylon i did the great one basketball with him he was just he had it like there's no question i don't wouldn't have had him on a countdown type thing i would have done something like he would have been awesome and inside the NBA if you'd put him in the shack seat he would have crushed it i think tarasie um would also be really good we had her on grayland basketball i think it was the show right before i left the s p.n and she was awesome she was so cool and it was we left that one

thinking like, and I really wanted to book her because I had seen her in a couple of interviews. I was like, I really want Tarasi. And she just crushed it in the seven minutes we had. I think she could have been really good. But yeah, I would say, I'd probably say, Mikhail and then Kobe. Favorite all-time Celtics beat writer. Bob Ryan, Steve Bulpit, Dan Shaughnessy, or John Powers. Did Powers have a season on then?

How does Jackie now make that list? Oh, sorry, Jackie. I'm sorry. And John Powers, he covered too. Right. There's the big five. Well, Ryan's... Cajic, Jackie would even admit this.

Bob's the best basketball beat writer who ever left. I mean, he would write... He created like the gamer. You know, I even... That PC had after they won the 81 title that used to be in the fours forever. The sports bar. Yeah, it was just...

It was so cool to just see that. the on the wall and read it. I just feel like, this guy wrote that that night. It's fucking great. I'll give you underrated for beatwriter. Michael Hawley, who has now become a national guy and he's on Peacock with Michael Smith and he has a Boston show.

He was a really good beat writer. And he was too good because they promoted him to call on this probably too soon. I wish he had stayed on the beef for a couple more years. But he did one of the Petino years and he was young and he knew the players and they trusted him. And he wrote this piece after one of the Petino years

about how dysfunctional the season was. That is still like one of the best beat, end of the year kind of word dump. What do you call those? But now they tell us. Certain cases they're in now they tell us. This was not a now they tell us. This is,

I can't believe they're telling us this piece because Petino was still there. And it was, the rumor was always, that that was why Bruce Bowen had to leave the Celtics because Petino thought Bruce Bowen was one of the sources. So they got rid of Bruce Bowen, who became this guy on the spurs.

And you could see in the moment was good. But Michael Holly was really good. Best Pro Basketball Book that isn't David Halber Stams, the breaks of the game. So this is your Desert Island Sportsbook. You can take the breaks of the game, but you only get one more. Sam Smith of Jordan Rules,

Terry Pluto's loose balls, Pete X-Telms the City Game or Jack McCallum's unfinished business I think you'd probably go loose balls because it's so much

fun to read it's just what is it like 500 pages of just ABA stories you can just go back to that all the time

I would pick that the franchise by Cameron Stoff was really good too about the Pistons I would have that on there

Unfinished business is a classic that's like that's a good one to reread because the access he got and some of the stuff he has in there is just nuts just Celtics trashing guys on other team like mcale trashing charles oakley um on down the line it's just that's a really good one i got a lightning round for you before you go yeah what's an NBA book that's never been written that you'd love to read i was trying to convince steve Nash to write one in 2009 when we had a bunch of e-mail emails about it about what would be in it. And after like the fifth email, he's like, oh, God, I could never do this book. Because he realized, like, I'm still playing.

There's no way. A book I always want to read or a book I would have loved to have read. I mean, some of them have been done. Like the Showtime Lakers oral history that Perlman did, I thought was an essential right kind of book. There's been some attempts in 2000s. I would love to read an honest assessment. of LeBron goes to Miami.

Because even, like, Levitard had a piece about Riley this week, and there was some stuff, there's so much bitterness still on the Miami side. There was something in there about how the whole LeBron side demanded hundreds of season tickets. And it just intimated that there was a lot more push-a-pull with Riley and LeBron than maybe we knew. And just in general, like the actual unauthorized account

of those four years. it would have to be somebody who was covering it at the time who also didn't care if they were burning some bridges, which is why it would never happen. But those four years, because then you also have, you have LeBron leaving CA and Rich Paul starting clutch and trying to steal all of CA's clients.

And there's just so much going. And then ultimately LeBron leaving in 2014 when they felt like it was probably headed that way, but nobody believed in it. And then just how much hate that team had in 2011, how they turned it around, how they achieved real greatness in 2013 and the Wade LeBron piece of it

and Wade had to give up the steering wheel. The right account of all that, the ship's probably sailed, but if somebody had had that book in 2016, it would have been an all-timer. You just don't get access like that anymore. You used to publicly lobby for the Milwaukee Bucks GM job.

Did you ever get close to actually working for an NBA team? No. Do you ever talk to an NBA team about working for? Might have talked to a team or two in the day. Interesting. Front office job? Yeah.

You know. Something. Something. The Bucks thing, I still feel like I was in the right on that one. If you go back and read the piece I wrote where it's like the theme was basically, you guys suck anyway? Why not think outside the box and let's try all these things? Wasn't the worst piece of the world.

first player or coach or GM who got really mad at something you wrote. Oh. I mean, the first I knew about was Isaiah. That was 2006 range. I felt like for the most part for the first five years at ESPN, it was people still trying to pretend the internet didn't exist, no matter who it was, whether it was radio hosts or whatever. And then by like 2006, 7, 8 range, it was undeniable.

But yeah, that was when then I would get some emails from people, probably that that's when it started that people like defensive emails but people not wanted to light me up because they didn't you know they were being smart about it but I remember like one GM who I won't name like sent me a really nasty email once and I was like cool I made it now I was like all right now I don't feel bad when I make fun of your terrible boobs and they continue to be terrible by the all right two more will you write another book about basketball uh I don't know. They're probably, I would say no.

I don't, I would doubt it. I'm just, I just want to be alive five years from now, Brian. I'm old. I'm pumping you for content. You just want to keep living. I just want to, I just want to be around. All right. Last question.

How many separate books would you break the book of basketball into if you had a read? Oh, my God. I mean, it would have been, I would say three. And I think I could have done all the stuff before the pyramid, probably longer. Because I had all how we got here chapter. And it ends in 1984. And the reason it ended in 1984 was I was out of time to hint in the book.

Like I didn't have time. I really wanted to go through every year. And it was about each year was about something that changed with the league. And it was one of my favorite chapters in the book. And if you read it, it just stops in 1984. I'm like, they figured out of everything. from here. It's like, no, they didn't. They didn't at all. And then the other piece of the book that's so frustrated to me is I just didn't have a lot of the, yeah, I spent three years working on.

I didn't have a lot of the footage. The games weren't on YouTube like they are now. Basketball reference didn't have box scores for stuff. I had the NBA help me out. A couple friends of on there, they mailed me like, you know, dozens and dozens of DVDs of the games so I could at least watch those and see what was going on. But now it would be like, so that. And then the advanced metrics, which when I was working in that book, the advanced metrics were pretty bad.

And then they slowly got better and better. And now it's like, you can, there's some stuff that's really helpful with, especially if you're comparing players. Now granted, the styles and the errors are different, but there's some stuff that would have really helped me. You know, like the,

the points per person. possession, shit like that, really would have been helpful. Breaking down something like Alan Iverson, who I'm going to defend forever anyway, but there's some really bad advanced metrics with him now that you have to look back and go, all right, was it helpful to have this guy when, you know, you were only scoring 91 points per possession and this guy took 30 shots? Like, is that a good thing? So there's just different questions I probably would ask.

Five-band lineup stuff too. I mean, the information is so amazing now. Sounds like a man he wants to write another book. Yeah. I think you should write a book. Where's your book? Oh, we're out of time, Bill. We had it.

We had the whole idea and everything. The hell. I'm sorry. We're out of time. Bill Simmons. Thanks for coming on the press. Good to see you, Brian Curtis. Huge thanks to the boss, Bill Simmons.

I'm Brian Curtis. Production Magic by Stefan Anderson. If you are new here to the press box, please take note. David Shoemaker and I do a podcast together. every Monday. We talk about stuff in the media, sports media, and beyond. And then on Wednesday or Thursday, usually, I do a big interview with a sportscast or a writer or occasionally a crime novelist where we get to go deep into their career and explore how they got where they are. We always

have more lukewarm takes about the media. We'd love to have you back. See you soon.