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Craig Calcatera
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Craig Calcatera
Dan Bernstein unfiltered unfiltered on 312 sports.
Dan Bernstein
It's an opening day DBU on 31 2. We are brought to you in partnership with my bookie and also today by Chicago Window Guys and Giordano's Pizza. My guest today is the author of the cup of Coffee newsletter. You may have known Craig Calcatera in his other incarnations as a lawyer, perhaps as NBC's hardball talk and some of the baseball expert work you saw him do for years there in the heyday of baseball on the Internet and is now doing what I believe is some of the smartest baseball and non baseball work every day. The cup of Coffee newsletter is something that is courageous enough to confront the everything every morning in a way that somehow doesn't make us miserable. Craig, thanks for doing this today. I really appreciate it.
Craig Calcatera
Thank you. That's very, very kind of you to say Dan. All that stuff.
Dan Bernstein
Well you know it's usually I will ask a guest as I did we had Joe Sheehan a couple days ago. We had Ray Ratto earlier in the week. My co host Matt Abaticola is on vacation so it's allowed for some of these longer form interview and usually I ask and I and I mean it when I say how are you? How are you doing? And in Your, in your case, I don't have to ask or I don't feel I have to ask. And I wrote down what I know. The answer is based on, on reading the way you feel every. When you wake up in the morning, you tell the world how you feel, good, bad or indifferent. So if I had to sum up, how does Craig Calcatera, how is he doing? The answer is okay enough, considering that's
Craig Calcatera
about the most perfect way to put it, actually. Yeah, like we're all hanging on by a thread for whatever reason. I just happen to have a place where every day I could write a couple of thousand words as therapy and to get it all out so I don't rant at my family all day. So you guys get that.
Dan Bernstein
Sorry, while we're gonna talk. No, don't be sorry because while we're gonna talk a lot about baseball and sports today and how it's how it fits into the larger culture. Because I love the fact that some people are afraid of context. Some people are told by their bosses, avoid context because it makes us nervous. You confront context, you create context. And I think that's what makes it special. And I think that's. There are certain journalists and writers, creators who are shining right now because of their, of their love for that kind of confrontation and awareness. So we talk a lot about mental health here and this has been something since this pod started seven months ago. And everything we do at 312Sports, it isn't exactly baked into our mission statement, but I do think it's really important right now to make mental health, especially men's mental health, non taboo. Just something that it's not just okay to talk about, but really important to talk about. We're hearing athletes echo it as well. So in your newsletter process, as far as baseball opening day goes, where does today fit in? Have you been looking forward to today? Is it, is it just another day that just changes up your routine a little bit? Or is this a reason to start feeling good?
Craig Calcatera
I will say that in years past, sometimes it is just another day, right? I mean, I've been writing about baseball for pushing 20 years now. And there's a sameness that comes in if you're a huge baseball fan, even if you're not writing about it. Sometimes you even get a little not sick of it. But it's like, okay, another opening day. It's just another series of the 2000 games we're going to play this year. Not this year. That's not how I'm feeling this year. I needed this. This year, I. While watching the game last night, the Yankees Giants game, I. I posted something on Blue sky that was kind of a joke, but mostly not a joke, and it was. I. I can't tell you how good it feels to be back online with a few thousand just abject weirdos complaining about baseball. It felt normal because nothing has felt really normal for, like, the last year and a half. And being able to care about something that kind of doesn't matter but is also enjoyable. And that is sort of a link to, you know, years and years in the past of everybody's lives. That is essential stuff right now, if for no other reason than for perspective.
Dan Bernstein
And yet you would think that it would be easy to slip into romanticism when it comes to the game. And you don't. You really don't. And it's. It's not all hope springs eternal, and it's certainly not Americana right now, which has a sour taste underneath. To. Everything that we talked about, everything that we love comes with a. Yeah, but in. In sort of that. That reconciliation in the back of our brain. But how do you balance both? How do you make it something that you're still really looking forward to and yet you love kind of taking the piss out of it more. More so than not.
Craig Calcatera
We don't complain about things we don't love. We. Indifference is the opposite of love, right? I'm critical of baseball. I'm critical of baseball's place in America. I'm critical of America. I'm an American. I love my country. But I'm critical of it because I care about it, because I want things to be better. My baseline has always been. Even before, however you want to characterize the modern day. My baseline has always been. Nostalgia is a trap. It's a prison sometimes. You've got to be careful of it. We all like to look back at the past. We all have fond memories. That's part of life. But the nostalgia part of romanticizing the past, overlooking its flaws and thinking, just as a matter of course, nothing can be better than it, that's. That's bad. That's. That's a good way to. To not progress in life. It's a good way not to grow as a person. If I think that the best baseball that was ever played was in 1984, and, hey, some days I actually do think that then I'm never going to appreciate baseball now. So you got to do whatever you can to appreciate the past. Walk that fine line, though, without romanticizing it, because it robs you of your Present and your future.
Dan Bernstein
I have to tell you, last night was tough, man. Where as excited as I was to watch baseball, I'm like, okay, first I do. What one would do is you turn on the television. And I did. And I said, okay. And I watch a little Bulls basketball, which is. Which is rough on the senses. And then I. And I get this feeling of baseball waves somewhere. And I'm thinking, okay, there is baseball on television. It may not be my immediate concept of television. Let's see where else baseball might be. And I found it on Netflix, and that is. That broadcast needs work, my man. That is. As much as I like some of the individuals involved, like, I thought CC Sabathi was fine. I think Hunter Pence is probably a prospect at doing some of that. I think there's some tools there. I think that he can. There's. There's definitely. But. Oh, boy. The. That. The interview between Matt Veskurgen and the commissioner, which thankfully was brief.
Craig Calcatera
Oh, thank God. For a 1, 2, 3 inning.
Dan Bernstein
Oh, my goodness. Like, if. If you ever wanted to. What do you mean the commissioner doesn't like baseball? What do you. I don't understand. How can the commissioner not like baseball? That is one to submit as evidence, I would think.
Craig Calcatera
There's never been an interview of Rob Manford where he seems like he really likes the sport that he's the commissioner of. I. I get the feeling that he could just as easily be the CEO of a software company or. Or a B2B insurance sales outfit, and. And he'd be fine because those are the things he focuses on, the bottom line and the process and all of that. And baseball just happens to be the MacGuffin that gets him up every morning. So I, you know, I could talk for 12 hours about Rob Manfred and his. His whole thing, but the. The broadcast, you're right, the interviews were crazy. It was a talk show interrupted occasionally by a baseball game. You know, we had Winston. You know, Jermaine Winston at quarterback, whatever.
Dan Bernstein
Winston. Yeah.
Craig Calcatera
What's he doing? I think that was some weird Netflix tie in for something else he does. We had the guy in the kayak out in McCovey Cove. We had both managers. We missed the first ever that it counts. ABS review. Robo ump review. Because they were interviewing the Giants manager and they totally missed it. I'd be like, you know, is that really being witnessed to history? Maybe, but it was kind of telling. So, yeah, I really think they've got a lot to work on. I think the central problem is I don't Think Netflix or whoever's behind that production trusts the game of baseball or understands the game of baseball or trusts its viewers to just watch a baseball game Today. When we watch all the opening day games, there's going to be a little intro that lasts about 30 seconds from a broadcaster, and then all of a sudden, you're gonna have the first pitch. That's what we want. That's what fans want. I think you just got to trust the game and do that. And that's where broadcasts go wrong.
Dan Bernstein
There's a lot of excitement in the air in Chicago, understandably so, certainly on the north side. I know we at 312Sports are excited because we just launched off the Ivy yesterday, which is our daily Cubs podcast. So we've got all that internal excitement around this team. But look, the Cubs are definitely good. They might be better than good. And I don't know what your, what your rule of thumb is about how long into a season it takes you to start, you know, grokking the vibes of a team, or if you have hard set data points in front of you, saying, now it's time to begin making judgments. But there is no question that a division title is a more than reasonable, if not minimum expectation for this year's Cubs team. And it's fun and it's a little daunting.
Craig Calcatera
Oh, yeah, sure. I mean, but I'm sure if you ask every player on that team, if you ask Craig Council, they love the pressure. That's what they want. I think that they're the favorites to win the NL Central. I think they're a pennant contender. I, I think, remember a few years ago, we always used to talk about how the Cardinals had that devil magic, like, God, you can't do anything about the Cardinals. They just somehow figure it out every year. The brewers have had that for a couple of years. They should not, by any rights have been the division champ the last couple of years. Cubs have underachieved. The brewers have overachieved. I don't think that holds this year. Brewers got worse. I think that devil magic can only hold so much. The Cubs got markedly better. I think they're the strongest team in the division. I think there's a lot of reason to be excited. As far as your question about, like, when do I think that it's real or not? Or when can you discount a slow start or not get too excited about a fast start? I don't have a hard and fast rule about it. If the slow start is because of injuries or something. Yeah, that's a problem because that could, that could be chronic all year. If it's just because of the ball's not bouncing the right way, I give it until like the beginning of May. Generally, I know we're starting the season a little earlier than we used to. Some people say Mother's Day, some people say Memorial Day. I don't think you go that far. I think you can kind of tell what's going to happen. By the way, beginning of May and in the wild card era, there's obviously a lot more room for error as far as becoming a postseason team. I still think you you can tell if this is going to be a wild card team or a division winner or a juggernaut or or a bunch of disappointments by around the beginning of May.
Dan Bernstein
Craig Calcatera, the author of the cup of Coffee Daily newsletter, is with us here on dbu. And you know what else resumes? Tonight is the tournament and the sweet 16 is starting. So now is the time to get in on the action however you like to do it. It's not just about picking winners. You like the prop board with player points, team totals. My bookie is your place to do it. One account, one wallet. You go to MyBookie AG with the code DBU. Your first bet is covered up to 500 bucks. If it doesn't hit, you got the bet back bonus token and you can run it back. It's one account, one wallet. You make your deposit and when you register, you use the code DBU for that bet back bonus token with your first bet covered up to 500 bucks. It's everything you want right now. You got all of these baseball games, all the futures opportunities, and in all this chaos lies all that kind of opportunity. Not to mention this big week. We will know the final four when we convene on Monday. So go to MyBookie AG, use the code DBU. Don't just watch the madness build. Make it pay. With my bookie we also have some tempered excitement on the south side of Chicago with the White Sox. It's one thing for the Cubs to be good, maybe better than good. The White Sox might be bad, but not as bad as worse than bad, which in its own way is kind of good.
Craig Calcatera
Does that make sense? Oh, I know. Totally. Totally. I think I was doing my previews the other day and I said something to the effect I was talking about the White Sox and the Marlins, and I said these might be the best bad teams in baseball. And I don't really mean that as a joke. I Mean, for the White Sox specifically, that's like a huge improvement. I mean, they were putrid two years ago. They still lost 100 games last year. 102 games, I think, last year. But they improved themselves. They really did improve themselves. You got to give them credit for not just standing pat over the. Over the winner. Are they going to be a playoff team? No. Are they going to be troublesome? Yeah, I think they'll be troublesome. I think they might be the single biggest reason why, say, Cleveland doesn't back into a division title again because, you know, you could always discount on how many wins against the White Sox, how many wins against them. While the Twins might be that way
Dan Bernstein
this year, but I think it's going to be the Royals who find those wins in that division, too.
Craig Calcatera
Yeah, the Royal, the Royals and the Tigers, I think, are the way to go in that division. But the White Sox, I like what they've done. I think they're a slowly improving team. A term I use is Frisky, which is not a playoff team, but interesting enough to watch. I'll actually watch White Sox games by choice this year because they're an interesting team in ways that they weren't an interesting team for several years.
Dan Bernstein
And the thing, too, is all you have to be to have an inexpensive major league experience in this town. You know, as someone who lives on the north side, you know, I live a mile to the west of Wrigley Field. We'll be down there after the show today, hanging out. But to get on the red line and zip down, to have to have two major league parks right here that really aren't that far apart at all. And for the White Sox to be able to do what they. They're offering the coolest little mini season ticket plan where for. I think it's for March, April, May, you can get tickets, but you don't know where your seat is until the last minute. And they'll just say, hey, here's a couple of tickets. You want to go to the game? Go to the game. And they're dirt cheap. And some of them, I think, even have options to get a dog and a beer or whatever it might be. But to do that for Major League Baseball and have the whole spin the wheel fun of where are we sitting? I don't know. Come on, kid, get in the car. Bundle up. We're going to a game. I think that's a. That's a great way to just to wake people up who are sitting right here in a town with two major league teams. And saying, get off your ass and go to a game.
Craig Calcatera
I think it's fantastic. And, you know, I won't get into my urban planning sort of lecturing here, but it's the sort of thing. It's the kind of thing that you can only really do in a city like Chicago, maybe New York, because, you know, I live in Ohio, I live in the Midwest. And even if I had a team in my city, which I don't, but even if I had a team, say I lived in Cleveland or Cincinnati or something, you got to think about parking, you got to think about traffic. You got to think about when you're going to leave. You can't impulsively just say, I'm going to go to the game, hop on the red line and get there. That's the beautiful thing. I've gone to a bunch of games in Chicago. One of my favorite days as a baseball fan I ever had was day game at Wrigley, night game down on the south side. It was fantastic. I think that's a great way to build baseball. We know how TV works now. You know, you can't just turn on over the air TV and watch 140 games. There are all these streaming services and cable. It's kind of complicated. There are all these ways that it's hard to get kids into baseball now, but, hey, I got a cheap ticket. Let's go down there on the spur of the moment. If your dad walked into your bedroom when you were like 11 years old and said, hey, we're going to a ball game, kid, that's like the best thing ever. You can do that in Chicago, and that's fantastic.
Dan Bernstein
So here is the game where it is as it is. You're wearing a Dodgers hat right now.
Craig Calcatera
I'm not a Dodgers fan. I have like 20 hats.
Dan Bernstein
We said this before. We've done all the disclaimers. You're a hat guy. So once you're.
Craig Calcatera
Because I'm bald.
Dan Bernstein
Yes. And because we're going to get to that, too. I tried to send you a picture of my pharmacists, but remind me to get to this, because I have to. You know what? I'll get to it now, because I'm talking about it. So when I started here at hubbard doing and creating 312 sports, we had to switch all of our prescriptions. Everybody in the family had to go from CVS to Walgreens because of the new insurance. It's better insurance. It's better, but it didn't necessitate. And, you know, we live in a big city. So it doesn't matter. We've got a neighborhood this, our neighborhood that. They're right next to each other. Doesn't matter. But both of the pharmacists. There are two pharmacists at our Walgreens, and it's at the corner of Western and Irving Park. You know which one it is. And both of them have Craig Calcatera vibes.
Craig Calcatera
It's like kind of bald, aging hipsters.
Dan Bernstein
Both pharmacists are middle aged, bald, be. Spectacled white men. So I was picking up and you know, it's your pharmacist. So there, there's intimate, intimate knowledge of what's wrong with you and your family. Right? I mean, it's. They, it's so they know, they look at everything like, oh, boy, you're.
Craig Calcatera
You're.
Dan Bernstein
You're upping your SSRI here. You feeling okay? Everything all right in your life? Well, your kid's crazy. Your wife is insane. You're. Your kids are what's wrong with your children. You're a terrible father.
Craig Calcatera
You know, even your pets.
Dan Bernstein
But just like, they can make so many judgments.
Craig Calcatera
Look, I got a cat. I have a cat that's literally. I've got a cat that's literally on Prozac, okay? I'm not surprised. The pharmacists know everything.
Dan Bernstein
I'm not surprised. So. But here's the best part. So. So he. He looked at me and he asked a question about the cubs. He says something about this is weeks ago. He goes, are they going to sign PCA to a contract? And I kind of gave him a look, and he's like, yeah, I listened to all the pods and I said, oh, well, thanks, man. I really appreciate that. And then he said, I do look like Greg Alcantara.
Craig Calcatera
There are a lot of us. There are a lot of us.
Dan Bernstein
So, yes. I don't know if he became a newsletter subscriber. And then the two of them were there, and I said, can I take a picture of the two of you? And one had grown a goatee, so it kind of messes up the vibe a little bit. But I said, I just got to take a picture of the two of you together because I never see you guys here. It was like the changeover between their shifts or whatever. And he goes, yeah, as long as you don't post it. He said, I trust you take the pictures. No social media. Don't put it up on YouTube or anything like that. So I, I will send it to you because they're in on the bit
Craig Calcatera
Which I wear type. I get, I get people in my comments and people that bug me on social media and they're like, Dan Bernstein's talking about bald guys or whatever. I get this stuff all the time because they heard me, you know, talking to you before. We are a type. We are, we are. There are millions of us. We're easy to ignore. But never underestimate balding, middle age white guys with glasses who are kind of meek and liberal. We're a type.
Dan Bernstein
You're a type. And, and also presumed to be privileged because I think there's, you know, we are. Right. You can be as self deprecating as you want. Like the self deprecation hides privilege. Oh, there it is.
Craig Calcatera
If I take the hat off and I actually shave and put, put on a real thing, I could walk in like anywhere and no one looks at me sideways. That's like, like being bulletproof. It's the superpower of the middle aged white man. Believe me.
Dan Bernstein
Yeah, you're kind of invisible. And then if we give you a neon vest and a clipboard, oh, you can get any anywhere.
Craig Calcatera
I could be on the tarmac at O' Hare in 10 minutes.
Dan Bernstein
You're only half kidding. I think we, we had Joe Sheehan on a couple days ago because, you know, this has been a time to just sort of delve into these conversations right around all the excitement of baseball. And I asked him about his, his setup and how he consumes the game. Obviously his sort of mission statement about his newsletter is, is different than what you do. You guys are in, you're on different channels, which I both think are essential to the baseball fan. I think you, you got, you.
Craig Calcatera
We've talked about that, actually. I know Joe. We've.
Dan Bernstein
Oh, you and Joe have you guys come in sort of on different wavelengths?
Craig Calcatera
Well, we've never like sat down and said, okay, you're a newsletter guy. I'm a newsletter guy. But we come from like the same background. Like, I've known Joe for like 25 years. We used to like Rexports, baseball and baseball, Think factory, baseball primer, all these sites in like the late 90s. That's how I got to know Joe. That's how I got into sabermetrics and eventually into writing. Joe is very influential in that regard. Back when I worked at NBC, he and I used to go on TV together and do stuff. So like we know each other very well. Joe is like really smart. Joe is quant guy. Joe is. He approaches the game in a, from a very different place that I do. I'm the liberal arts wing. He's. He's more of the hard sciences is kind of the way I think about it. And in that way, it's sort of complimentary goods. I have tons of readers that are also Joe subscribers, and he can say the same. Whenever I'm running a sale or when, like, today's Thursday and my newsletter is free on Thursday for anybody who wants to read it. Joe's always out there, like, retweeting my newsletter to people. It's a. It's a really nice, complimentary good thing. If either of us were better business people, we could probably figure something out. But we both exist in the same universe and it's really nice to have somebody else that knows what you do and you know, what they do.
Dan Bernstein
I think it's really cool. And it, it's. He was explaining how he consumes the game once the season begins. And he works hard, man. It is. There's a lot to do and a lot to know. And you're not just covering baseball. You've got a lot of different antennae pointed in different directions or maybe into deep space at this point looking for some other alien intelligence to come rescue us, like the giant SETI radio telescopes that are sitting out in the desert. But when you start a day's work knowing you're going to get up at whatever, 5:30 or whatever you do, how do you plan around your baseball day? Are you looking at matchups? Are you looking at potential leverage moments? Or is it like, hey, I'm going to start with this game, branch out to that game? I'm just curious, especially now with games that do move faster and are easier to consume for the most part. What's your setup?
Craig Calcatera
For me, it's way easier than it is for someone like Joe. They're working on a granular level. The stats of the people at Baseball Prospectus and fan graphs, and they are looking at baseball at a very granular level. I've come from a very different place. The way I view it is I am writing for people who were like me when I used to work in an office. I've got a life. I've got a lot of things I need to do, but I just want to catch up. So, you know, my newsletter every day is. I'm recapping the night's games from the night before. I'm giving you a digest of all the baseball news and stuff. I don't. I'm not the guy that you go to to say, you know what, so and so's batting averages on ball and play against lefties. That's like, I am not that guy. So in some ways, I have a much easier job than someone like Shein does. What I do is I, you know, I'm scanning the headlines. I'm looking at social media. Like, I've curated my social media over the last, you know, 15 years to get the newsmakers, to get the people who release information. I'm just trying to see what's going on so I can tell people who don't have the time to waste their entire day on the Internet, like I do, what, what's really happening. And I tend to write most of my stuff the day before. So it's all the news that's going on on a Wednesday is going to be in Thursday morning's newsletter. So in some ways, I have it easy. I'm doing what I used to do back when I was a lawyer, wasting time and working my way out of that profession, which is looking online and just talking about it. But now I get paid for it.
Dan Bernstein
If you can see behind me here, you see that, that, that, that's a window. And people might say, oh, yeah, you always talk about your windows, Bernstein. Well, I do, because Chicago window guys and Russ Armstrong have taken very, very good care of me. And they will do the same for you. If you are thinking, oh, boy, that air conditioning is gonna get expensive and all of our costs to heat and cool and all of our costs and life are going through the roof, what can I possibly do? Well, as the environment might be going crazy, you can certainly keep your environment in your home the way you want it with really good windows from Chicago window guys. And this is not some big window thing that you hear about all buy one, get one free. This is Russ Armstrong. He lives here in Chicago. His factory is here in Chicago. Russ will come to your house, he will talk your ear off about curling. The man loves curling. He's really into it, and I suggest you talk to him. But he's. He's a great dude. He's going to explain to you stuff about windows you're probably not going to understand because I just said, russ, man, I trust you. You know windows better than I do. You got good ones, we'll do it. And he said, I gotcha. And he did. And they're all hits, his crew. It's no subcontracted labor, no third parties. He measures everything. He custom makes the windows for your house at his factory here. He will match any price, too. So if you're worried about price, he's going to explain why this other stuff that you hear these, this stuff is gimmicky. Just call him 847-302-9171. Check out his five star reviews at ChicagoNowBeyond.com and when you're getting quotes, ask other people who's installing my windows. They won't know because they use third parties. Russ doesn't. He's going to know everybody in and around your house and if that makes you more comfortable, it should. And that's why he does it. So call Russ 847-302-9171 and check out his 5 star reviews at Chicago window guys.com I know that there are the Cubs fans who like to think baseball's better when the Cubs are good, that the Cubs mattering is just there's something grounding to baseball when the Cubs are good. And Cubs fans love feeling that, love thinking that. I don't know if it's true. Is there does it add something better to baseball, to the discussion because of the Cub fan diaspora that somehow exists? Is there still lingering post? It's can't believe it's 10 years ago already the Cubs won the World Series. But do you agree with that statement generally that there's something extra or more fun or different or better if the Cubs are in the conversation as good?
Craig Calcatera
I think so. I actually do. And it's weird. Well, first of all, I'll say it's weird because people sometimes say that about like the Yankees or whatever. No, I don't think that at all about the Yankees. I don't think about the Red Sox. And it's not just because they had a couple of decades of like really, really good play. There's something about the Cubs part of it. You mentioned the diaspora. You know, like everyone else who didn't live in a major league city, I saw a lot of Cubs games when I was growing up because of wgn. Right. You, you. The Cubs are a national team in lots of ways. For anybody who I think is over like 35 years old, probably the Braves were the same way. In a lesser extent, I think. So we all have the idea of coming home from school turning on a game on wgn, no matter where you lived. I was in West Virginia, for crying out loud, and watching a Cubs game. It might have been the only game on. It usually was the only game on, especially before the lights. So there's this, I won't say love of the Cubs because it doesn't necessarily make Cubs fans out of everybody. That whole dynamic didn't. But Knowing they're there, seeing a full house as opposed to a half empty house, Seeing an interesting team as opposed to a not interesting team really would brighten up my day for, you know, 25, 30 years when, you know, before they. Before they stop being sort of a national team like that. I also think that a big city like Chicago, when a big city has a good team, there's something infectious about it because you can get that B roll. If you're even back when you used to watch SportsCenter, you see the city B roll, you could see people, like, enjoying it again. We're getting into urban planning a little bit, but you walk down a street and you see five bars that have Cub stuff out and people wearing the stuff on the sidewalk or on the train or whatever. There's something I hate. I'm never like this. I'm not woo, woo about baseball at all. But there's something really nice and almost magical about it. So I'd like to see the Cubs do well, even though I very rarely, if ever, root for the Cubs.
Dan Bernstein
All right, let's. Let's get into the important stuff here. And this is kind of what. What I've been waiting for for a bit. Your music taste I find really interesting because every. Every. No, seriously, every time I think I've got it pinned down, you'll throw a curve in there because it would be really easy to pigeonhole you as. Or horse rock, whether it's driving truckers or the national or something like that. And then you'll throw some new wave curve at me. How do you decide? As a fan of music and someone to whom music is important, sort of spiritually and generally, and you talk about what it can do for you, how do you make sure. And this is something I'm trying to do as well in my old age, is while settling into long understood patterns that feel good and comfortable with also testing yourself, with also challenging yourself and saying, you know, my kids are listening to King Gizzard and the Lizard wizard, and I'm gonna get. You know what. But seriously, I had one of my former producers, huge fan of King Gizzard, and I thought there was, like, some joke you were making about here's. Here's Carlo really wanting to see these bands. And I try to do the same with. With mine a little bit. But how do you manage that? How do you say, all right, I'll. I'll. I'll give it a run, I'll give it a fair shot to see if I like it?
Craig Calcatera
I think that's the way to do it. It's the fair shot. I'm not gonna lie. I am nowhere near up on. You know, I. Look, I had reason yesterday to look at the Billboard Hot 100 for something I was writing and I was going down to see, okay, how many of these acts do I recognize? Yeah, we're at a pretty low number in my lifetime of recognizing the Billboard Hot 100. But like you mentioned, I have kids that now they're 20 and 22 years old, and you pick up a little thing, few things through them. You hear about stuff through them a little bit. And 99% of what I'm listening to is probably music of, like, my generation as far as, you know, 80s, new wave, British new wave. I'm really big into listening to a lot of 90s Britpop. Up until around. Magically up until around the time I had little kids, you know, I was pretty current. But you got to give it a shot. The thing I hate most is if you go on Facebook or you go somewhere else and you see someone post something from, like, 1974 and go, that's when music was real. Come on. That's just when music. When you were young. And there's nothing wrong with loving the music you love when you're young. But my kids have that for music that came out in 2019, and their kids are going to have that if they have kids that comes out in 20, 30, something. There's always good stuff coming out. And even if it's not for you, at least give it a chance. Don't just be rejecting it out of hand. And then do what I do. Go back and listen to the same 20 artists you always listen to.
Dan Bernstein
Where does music fit actively into your mental health routine? Do you think about it consciously and say, hey, I need to listen to something now that makes me feel a certain way, or do I need to set aside time for music that makes me feel a certain way? Or is it just sort of where it is when it is? And then you make the mental health aspect work. How actively do you use music?
Craig Calcatera
For me, it's like when I won't say, it's 100% of the time that I'm thinking in terms of music in that way. If I'm not doing well, if I'm, you know, depressed or if I'm going through hard stuff or whatever. Absolutely. I turn. There's a lot of music I'll turn to because, like, you just get this catharsis that loud music can only help you with. I'll put in my headphones and I'll listen to something that'll just make me feel something, whether it's depressed, painful, whatever. That, that helps me get through hard moods and you know, it's almost a cliche. Sad songs make me feel better when I'm sad. And it's true. It does, it does help. So that's a huge part of it.
Dan Bernstein
Okay, so you lean into that direction.
Craig Calcatera
Oh, yeah.
Dan Bernstein
So you're, you. So you're gonna actually like allow yourself to indulge whatever those feelings are and then you get the opposite effect.
Craig Calcatera
Absolutely. Because in my own life, and I'm speaking, I'm speaking just for me, but I'm sure there are a lot of people like me. Just like there's a lot of bald glasses guys at the pharmacy. There are a lot of people like me.
Dan Bernstein
I'm not judging right or wrong. I'm just, I just. Because I know there's some people, look, I. Who say I feel like shit and I just, I'm just gonna rock out with some Ramones or something like that and others.
Craig Calcatera
And that's totally valid.
Dan Bernstein
Or you want to wallow or you just, you want to put on, you want to hear Matt Berninger's baritone and then that's usually thrown in the back of your head.
Craig Calcatera
Okay, well, I mean, the thing is, I. A middle aged dude like me doesn't necessarily. Wasn't really taught to connect with his feelings very well. You're, you're, you're sort of taught, especially as a man in society, you're taught to, to hide your emotions, to, to push that stuff down and power through. And there's a huge amount of that to my personality. And so if something's bothering me in my real life, I might reflexively say, I don't want to feel this, I don't want to think about it. But if I turn on the saddest song possible, you can't not feel something. In some ways, you can transfer what you were feeling in life through that music. And it'll help you touch emotions that you might be hesitant to feel just in the normal day to day. So that's, that's why I think the wallowing comes in. That's where I think leaning into those feelings come in. It helps you feel things you might not have otherwise felt.
Dan Bernstein
Weird question, but somehow there is a band that I missed completely because when you have kids, it just throws everything off. All of a sudden you're listening to the Wiggles and Lori Berkner and Dan Zanes and hey, Laurie Berkner is legit. Oh, they all so stand. We saw Dan Zanes here at the Harris Theater. He was unbelievable. We went to see the Wiggles at All State Arena. God, that was an expensive ticket those guys have. They've got to have yachts like Dr. Dre right now. I mean, just.
Craig Calcatera
Oh, man, kid entertainment. They print money for kid entertainment.
Dan Bernstein
I know you, me and Joe Sheehan, we should probably start a group and wear different colored shirts and bounce around. It'd be lovely. But so one band I completely missed and have gotten and they're trying people like, you know, because I asked around and there was. And the questions, the answers I've gotten about them have been really mixed. What do you think of Ween?
Craig Calcatera
That's a. You know what we. I was in college in the 90s and there was a record store I would go to, to Ohio State and there was a record store on campus that would always be playing Wean. Selling weed. Had all the Wean posters. I remember the Chocolate and Cheese album, I think it was called that came out. I never really listened to them much because I appreciate there's like this arch irony to Wean, you know, where they're. They're trying on styles, but they're doing it faithfully, I think, you know, they did like a country album, like a. Like a early 70s Nashville, cosmopolitan country, you know, with strings in the whole deal kind of album. I remember. I. I appreciate Wean more than I enjoy Wean, I guess is what I would say. I get what they're doing. I love what they were doing back then. But it's never like I would never just click on Ween, you know, that's just not a thing I was doing okay. It's a very, very smart guys fan, but I never really got into them very deeply. More than an appreciative level.
Dan Bernstein
I think that that's an interesting way of summing them up because I. I'm not sure I quite get the bit because it's one of the ironic detachment. It's another thing. Sometimes it is. But there are these transcendent moments within the bit where every once in a while you're like, holy shit, these guys could have been a great band but didn't want to take it seriously enough. Like they, they. Every once in a while you come right up to something, whether it is a pop hook, you know, something like a little kind of groove in there that's almost like a. Like a Fountains of Wayne type little hook in there. You're like, damn, that's. That's legit. There's. There's Beatles stuff and like, you say Grateful Dead, country influences in there, and. And then they break the spell with some ridiculous lyric or they. Or they go off noodling in some direction and you. And I just want, like, could they have been a legitimately great band?
Craig Calcatera
I think there's like, an analogy to be made between, like, ween bands like Ween and then, like, comedians who act dramatically in roles, right? It's like you'll see a comedian, just Adam Sandler in, like, Punch Drunk Love, knocking a dramatic role out of the park, but he's still Adam Sandler. It's like, you can't be funny if you don't have a baseline of talent to where you can work from, you know, work from. I think it's harder. That's why I think comedians in a lot of ways are more talented than a lot of dramatic actors is they have to have that baseline in order to then jump off from that and do other things. I think bands like Wiener the same way you can't play around with genres if you're not really, really solid musically in your instincts and your technical ability and everything. And you mentioned that band King was King Gizzard. It's like my son's favorite band. They're the same way. I mean, King Gizzard, they're very prolific. They put out like, a heavy metal album, and then they'll put out a jam band album, and then they'll put out, like, math rock or something that sounds like, you know, you know, like German. Yeah, yeah. Or they'll do like a Prague thing. It's. You have to have, like. If you. If you don't have a baseline of real strong competence, none of that stuff is going to work. And so that's why, again, I appreciate it, but it's, like, hard for me to, like, get in the vibe because it's so eclectic.
Dan Bernstein
Said this before, if you're not subscribed and you're a baseball fan, that's going to be your hook because you're missing out free Thursdays. You can go check out cup of coffee today. And once you read that and you realize, you know, it would be nice to wake up to something like this every day because if Craig goes down a Wikipedia rabbit hole, he's gonna drag you down with him and he's gonna be your tour guide and he's. And you're gonna be. You're falling head first down whatever rabbit hole he's going. But the cool thing is you don't know where it ends up. But he's pointing out interesting things along the way that he sees or he interprets. And then you say, oh, I didn't think of it that way. Or I didn't know. This obscure note in British history that somehow is going to make me feel better about my day today because it's a perspective that I never had. So we love talking with you.
Craig Calcatera
I did like hundred words on the Norman invasion earlier this week. So you know.
Dan Bernstein
Yeah, I know. But everything. But it all comes to, it all makes sense. Or, or you do explain. Hey, here's why I'm going here, here's what I'm feeling, here's what I'm reading, what I'm doing. And I'm always along for the ride.
Craig Calcatera
There's always at least some point to it, even if I occasionally forget it, which is, hey.
Dan Bernstein
Or if I forget it too, I can always go back. That's the thing. Because it's there.
Craig Calcatera
And see, that's the thing.
Dan Bernstein
All you get so many moments.
Craig Calcatera
You're a radio and a podcast and a video guy and everything like that. And that's great. And I, you know, I'd probably be way better off in life if I had gotten on that train. But me and the written word have to go together because you got to be able to scroll back and wait, what is he talking about? So I'm, I'm forever going to be in the written word primarily.
Dan Bernstein
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Craig Calcatera
A couple of them are very obvious. Shohei Ohtani, obviously I really think he's the best player in the history of baseball. I won't get too down that rabbit hole, but we are watching history every time he plays and so I will always try to see him. The two big pitchers in baseball right now, Tariq Skubal and Paul Skeens, obviously you want to see these guys. I hate to say it, but you want to see these guys before they blow their elbow out and miss a year and a half. But they are worth the price of admission. Less so on the like super, super superstar level. There are two guys, both in the NL Central who I will always stop to watch and that's Ellie De La Cruz and o' Neill Cruz. Pittsburgh and Cincinnati. They're flawed players in a lot of ways. I mean they're not like the best players in baseball, but when those guys are on, they're ridiculously talented. They hit the ball so hard. They're such slick fielders. They have amazing arms. I love watching super athletic guys like that. My favorite player to see ever in my life who wasn't necessarily the best player, but my favorite one to watch who played during my lifetime was Eric Davis back in the mid-80s. Guys who have speed, power, defense, the whole package. And their excitement, like there's this coiled energy about them. De La Cruz and o' Neill Cruz are like that and that's why I like to watch those guys.
Dan Bernstein
What's interesting from your perspective is you don't have in some ways a default team and you talk about going to Columbus Clippers games and you mentioned that and we talked about the experience of going to games. But you, it's unique that you were not a born and bred Yankees fan or whatever it may be. You didn't grow up in the Bay Area and have this, you know, whatever it is, a childhood Giants fandom. Where, where is young Craig baseball? On what team did you imprint? What broadcasters created this? Like the. Everybody's got a, an a pretty specific individual experience. And yet you have moved, you've lived in certain places, you know, you've mined your family tree itself for a ton of content and things outside of baseball. And now as a middle aged person, you've got a fully actual baseball fandom that doesn't really have a single origin. And I think that's interesting.
Craig Calcatera
It's weird part of it. I've never lived in a city with a major league team. I even lived in Washington D.C. for three years, but it was before the Naps got there. But I've been in, you know, I grew up in Flint, Michigan until I was about 11 years old. I. What I didn't have was parents handing you the game. You know, my dad didn't teach me, but there's no sports in my family. My, my parents were not sports fans. My grandparents, I never, it was my brother and I got into baseball cards because we thought they looked good. And then since we lived in Michigan, I found Ernie Harwell on WJR in Detroit in the late 70s when I was like 6 years old. And so Ernie Harwell and those Sparky Anderson tigers until the mid-80s, that's where I imprinted. That's where I really got into baseball.
Dan Bernstein
Is that what you said? 1984. Is that why, is that why you happened to literally mention the year 84? Okay, wire to wire. Tigers.
Craig Calcatera
It's possible. And that was the last year I lived in Michigan because we moved away. Right. So you can't. And back then you can't take your, your local fandom with you. And I was in West Virginia and there's no team there. And so I had a choice of the Cubs or the Braves because Cable and I, for a bunch of weird reasons, I gravitated more towards the Braves. So for many, many years I was a skip carry watching the Braves on WTBS fan because that's what I had and that carried for a very long time. But I was never like the rah Rah, love them no matter what kind of fan. But they were my team through the Maddox years and everything. Although I liked them better when they stunk. Like in 87, 88, 89, 90. Those were my favorite Braves teams even though they lost 100 games a year. For a bunch of dumb reasons, you know, and then you grow up and you work and you don't watch as many Braves games. And me personally, I got really deeply into baseball on the Internet in the 90s. And you sort of follow every team when you're doing that, when you care about roster construction and drafts and, and all those sabermetric kind of things, you start looking at every team. And I think that's kind of what led me to do what I do now is I was able to talk about every team, you know, 20 years ago in ways that a lot of people couldn't. And the Internet comes up and then you just start writing about it. There are 10 guys within a block of me who could tell me way more about the Cleveland Guardians than I could ever say, but I could talk about 30 teams and I kind of do. And when you're a writer, national sort of way, it's hard to get into fandom again. I will say this much though. My, my wife Allison, we've been together about 14 years now. She's originally from Michigan and she inherited Tigers fandom from her father and she's a big Tigers fan. And so in the last decade or so, I've kind of eased back into the Tigers a little bit. Not necessarily in a hardcore fandom way, but we watch more Tigers games than we'll watch other ones. I like to see them do well and they're three hour drive from me, so I'll go up to Tigers games a few times a year.
Dan Bernstein
More importantly, you get Jason Benetti in your life.
Craig Calcatera
That helps. That helps.
Dan Bernstein
And he's, you know, my former intern and you know, we, when he was, when he was in college at Syracuse, he was a willing, if not supremely talented intern specifically for the Boars and Bernstein show. But one of my favorite people in, in and around sports right now. Just an absolute fantastic human being and, and when. And a broadcaster who understands the context of what he's doing, what's important, what's not important, where he fits in everything, and to know your broadcaster knows that is incredible. Incredibly. It's not the word I'm looking for. Connective. It's not, it's empowering, it's connective. To know that the eyes and ears bringing you your team are a like thinking person.
Craig Calcatera
Benetti is a huge bonus of being a Tigers fan right now, and I'm sure White Sox fans could say the same thing. I'm so happy that my former employer, NBC, has hired him to be their first voice on their new national game package. Because he's the best. And I think what you're talking about gets at it. There's, there's a sameness among the, the, the younger generation. I mean Benetti's not 25 anymore, but it's like there's a sameness among the younger generation of baseball broadcasters that for as good as Syracuse is and it's like the place to come from if you want to be in broadcasting or sports writing or whatever. But I think there's almost like this Syracuse style that is sort of affected a lot.
Dan Bernstein
It's the same voice. I, I, I have a difficult time. It takes me a second to know who's talking because there is such a similar sound and there's a craft to
Craig Calcatera
it that you could appreciate, but it is similar and there's this element to it of everything happening in this game right now is the first time it's ever happened and the most important time it's ever happened. And we know that's baloney, we know that's not true. And the good thing I like about Benetti is It could be August 11, the team's 14 games out of first place. It's a Wednesday night game against another non contender. He's not going to like make you feel like this is the most important thing that ever happened, but he's still going to be entertaining, he's still going to be excited and that's pretty rare in broadcasting these days.
Dan Bernstein
Something else I want to talk to you about outside of baseball was something you, you helped us with last summer when Beth and I took our trip to England and knowing what an Anglophile you are and you gave us recommendations for some of these walks in London and just sort of how you know what to do, what not to do, which sort of MAGA owned pubs not to go into and that some of that stuff was very helpful. But the nature of travel, and I always think about it and travel is first and foremost a privilege that there's no question that the ability, ability to get outside one's comfort zone is, is, is privileged because it means you have both the time and the resources which are both very, very precious things. I'm aware of that, but I'm also aware of its, its, its boundless value to increasing our empathy and increasing our awareness and say that there are, wherever one may go, there are aspects that can challenge our worldview, can make us understand someone else's a little bit better. And do you think that's why? Because you've got some literal wanderlust in you as much as you love walking and hiking, I've learned to like that, too. For me, that's fishing for me. But I've learned to do a little bit of both. I've learned to do a sort of a. A peripatetic urban fishing style that does also keep me on the move and meeting people and moving around a little bit. But when. When you can't actually go somewhere, do you bring other things to you? Do you find a way in all your time? You say you are a creature of the Internet. This allows you some quote, unquote, travel opportunities, if you're mindful of that as well. So how do you make that a piece of your life and how you feel?
Craig Calcatera
Well, if I'm not actively traveling, one thing I'm often doing is I'm just like, on Google Earth or I'm on Maps or anything like that. I'm just fascinated by looking at different cities, different places. The Internet is great if you. It's hard now because everything gets funneled to, like, the same seven sites. But if you can break out of that and remember what the Internet was like in 1997, you could find people who, say, have a travel log they wrote themselves from the time they went to Portugal, or someone hiked the Appalachian Trail, or, you know, someone, I don't know, took a raft on the Mississippi river, whatever. Reading about other people's experiences is a huge thing for me. It's, you know, it's a hobby, it's idle sometimes. It gives me ideas of things I want to do. But I think the real important thing, especially now when so many of us, you know, I work, I've been working for. From home for like, 16 years now, 17 years almost. And when you don't have to leave your house a lot, your world gets a lot smaller really quick if you let it. And you got to fight back against that a little bit. I am just as bad as anybody else about that. I'll go four days without leaving my house and then forget that I haven't left my house. But you got to find ways to break out of that. It's a challenge. But I always feel better when I do. And, you know, my wife and I will go to shows, we'll go to rock shows, we'll travel a lot. We're going to England again next week because we're. And, yeah, there's a band. We're going to England to see a band come on. And it's. You have to break out of your routines and your sameness as much as you can Even if you're a person like me who is a creature of habit and a creature of routine, it's better for you, even if it's hard.
Dan Bernstein
And especially summer in Chicago. I always mention this, and I hope that anybody who's watching or listening to this understands that one of the most wonderful aspects of Chicago are the fact that our neighborhoods here can be little worlds. And to be able to take a beautiful afternoon. And it doesn't have to be a festival, but there are. There's festivals. There's every nationality, everything in this city, if you just look it up. You can go to a Guatemalan festival. You can go to a. There's a million different Greek celebrations. You can go to Humboldt park and be deep in Puerto Rican culture. You can go to Pilsen and feel like you're around people who understand different regionalized Mexican cultures, even Polish in the city, Ukrainian. We're unbelievably lucky to have that. And it's just something that I urge, especially with little kids, because one thing you do with little kids is always look for. What do we do? Oh, my God, we got to fill another four hours. How am I going to entertain these people? I'm out of energy. What can I possibly do? If you're lucky enough to be in a big city or close enough to one, instead of going to the big touristy magnets all the time. Neighborhoods, neighborhoods, neighborhoods. And there are so many discoveries awaiting you that I always say that you don't have to really go that distance to truly travel.
Craig Calcatera
There's that truism. I mean, it's very true, actually, that Chicago is sort of the magnet for, you know, everybody from the Midwest. You know, you end up in Chicago. People come out of all the big ten schools and go to Chicago. Chicago, my. My son goes to school at Ohio University, and half the people he's going to graduate with want to go to Chicago. He just spent spring break up there. My daughter goes up there. It's. And that's the reason, right? It's like, I know New York has that, but, you know, when you live in the Midwest like I do, everybody looks to Chicago for that. And the times that I've been up there, which is, like, countless times, it's exactly what you're describing. It's the, you know, the neighborhoods and the ethnicities and just the way that everything is just sort of at your. At your fingertips. And I'm not talking about, like, the luxury amenities. The theater is great, but I don't mean that necessarily. You know, the ball Games are great, but I don't mean that necessarily. Just being in a place that doesn't have a sameness, that isn't just a bunch of like minded people and similar looking people and people with similar backgrounds, you know, that's why I left the suburbs and moved downtown where I am. But Chicago's got that in spades.
Dan Bernstein
Are you still hanging at the same local bar that you liked?
Craig Calcatera
Oh yeah. So I've got my, my son graduated high school three years ago and we moved out of the suburbs and down to downtown Columbus to a neighborhood called German Village before graduation actually, but the minute we could where he wouldn't be taken out of school and I am literally 400ft from a dive bar. It's called the Back Tavern. If you're in Columbus, Ohio, check it out and it's right down there. And that kind of thing is a real nice thing to have that when you live 18 years out in the burbs, you forget about no question.
Dan Bernstein
Well Craig, thanks for doing this. Thanks for I really appreciate you taking the time to just hang out and A happy opening day, a happy healthy baseball season to you and yours. I hope your UCL is okay. I hope all the individual parts of your rotator cuff are okay and your arm feels good and you can help the ball club.
Craig Calcatera
I'm day to day like everybody else.
Dan Bernstein
Thank you Craig for joining us. I appreciate it. That is Craig Calcatera. If you are not subscribed to the cup of Coffee Daily Baseball and More newsletter, I think you're doing it wrong but that's just me. You know, whenever the stakes are high, my bookie is where you can turn bets into bankroll. And you can certainly do it now with the matchups on this schedule, all the baseball, the the college basketball for some this is the best weekend. Going from 16 to 4. It's the, the, the best. As far as the quality of games and the number of games, this may be the best four days. My bookies prop board is deep and fun to play. You've got player performances, game milestones, everything between. It's the kind of action keeps things interesting all game long. So if you ever wanted to get in, get in right now. One account, one one wallet bet the spread live bet during the action, jump into the casino during halftime between games. Everything lives in one place. So go to MyBookie AG. That's where it all is. MyBookie AG. Use the code DBU and then your first bet is covered up to 500 bucks. If it doesn't hit you've got the bet back bonus token and you can run it back. That's DBU as your code at MyBookie AG. Don't just watch the action, make it pay with my bookie. A reminder that tomorrow I'm going to be here. We are going to be doing our top 10 list and Friday feedback Friday and more tomorrow. We have much to discuss and looking forward to it. If you want to come hang with me today, if you are hearing this and if you're headed to the Cub game right around when this is posting, I'm going to be around at the Cubby Bear with WDRV97.1FM. We're giving away stuff. So if you are hearing this, if you're headed to the Cub game and you want to come to the Cubby Bear and say hello, we'll be there right up, you know around to the the start of the game today. So come by and say hey, big thank yous to Chicago Window guys. Russ Armstrong at 847-302-9171 thanks to Giordano's order delivery now@giordano's.com and we are brought to you here in partnership with my bookie Dan Bernstein.
Craig Calcatera
Unfiltered Unfiltered on 312 Sports.
Date: March 26, 2026
Host: Dan Bernstein
Guest: Craig Calcaterra (Author, Cup of Coffee newsletter)
Producer: Matt Abbatacola (on vacation)
Podcast: 312 Sports
This Opening Day episode of Dan Bernstein Unfiltered dives into the excitement, context, and culture surrounding Chicago baseball as both the Cubs and White Sox launch their 2026 seasons. Dan Bernstein welcomes renowned baseball writer Craig Calcaterra for a candid conversation about the meaning of Opening Day, the intersection of sports and mental health, the state of baseball broadcasting, the strengths and weaknesses of this year’s Cubs and Sox, and the ways in which sports fit into the broader lives and identities of fans. The two also share thoughts on music, urban life, and finding wonder in Chicago’s neighborhoods.
[02:12 – 07:56]
Baseball as Stabilizer & Context:
Baseball Without Sentimentality:
"Nostalgia is a trap. It's a prison sometimes. You’ve got to be careful of it... If I think that the best baseball was ever played in 1984, then I'm never going to appreciate baseball now." (06:47)
Mental Health and Openness:
[07:56 – 11:04]
[11:04 – 13:25]
[13:25 – 15:44]
Not Good, but Not Hopeless:
Engagement via Accessibility:
[16:06 – 18:36]
[18:36 – 22:41]
[22:55 – 27:07]
[29:51 – 31:51]
[31:51 – 37:41]
"Sad songs make me feel better when I'm sad... It does help." (35:33)
[45:46 – 47:11]
[47:11 – 51:19]
[51:19 – 53:45]
[53:45 – 57:26]
[57:26 – 60:05]
Craig: "Chicago's got that in spades... At your fingertips... Not just the luxury amenities. Just being in a place that doesn't have a sameness." (59:02)
The conversation is open, sharp, and culturally aware, mixing the breezy humor and wordplay both speakers are known for with sincere discussions about mental health, fandom, and the role of sports in life. The style is conversational, self-deprecating, and occasionally digressive but always with the intent to connect big ideas back to baseball and daily routines.
Special thanks to Craig Calcaterra & Cup of Coffee
For more, check out Craig's newsletter especially on free Thursdays!