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Grant Brisby
This is the Wind Up. Welcome to episode number 178, the Roundtable. My name is Grant Brisby, here with Sam MILLER and Andy McCullough is rejoining us. Andy McCullough, how are you doing today?
Andy McCullough
I'm good, Andy.
Grant Brisby
You know, we don't like to, to tell people where, where the other co hosts are, you know, in case their house gets robbed or something like that. But Andy was in Croatia. Where else were you, Andy?
Andy McCullough
My wife and I attended a wedding. Not our own, but a different wedding in Edinburgh. And so yeah, we went to Croatia for a few days afterwards. Just a little vacation before the postseason. So I went to Split and went to Split in Dubrovnik.
Grant Brisby
Was there any Andy McCullough? Like there's a spotlight in the shape of Andy McCollo, and it shines into the sky whenever a news story that only Andy Micola can tackle. Was there anything that say happens like that while you're in Croatia?
Andy McCullough
There was. Yeah, there was. Tyler Hyneman had a really bad performance, and they were like, no one can write about this better than Andy. Yeah. So Clayton Kershaw announced his retirement. Not surprising. I think, that he's decided to walk away after this season, obviously, given the way the last few years have gone for him physically. He pushed really hard to get back and have at least one close to full year coming off shoulder surgery, and he was able to get that this season. A little bit surprising in the way that he kind of announced it, but I, As I suspected might happen, you know, his. His wife and his family were pretty adamant that they wanted to him to have kind of a moment to say goodbye to the fans at Dodger Stadium in case he's never. He doesn't make another start there, which is looking like he's not going to start for them in the postseason now. And so, yeah, I got the message from. From. I had heard through the grapevine that it was. Was happening. I had had, you know, some conversations with him a couple weeks ago that led me to believe something like this might be going down, but he's always kind of, you know. And then I got a text from former host of the show Mark Krig, basically saying, hey, we need you, big guy. So the.
Grant Brisby
That's not what it said. That's not what the text. What did the text actually say, Andy?
Sam Miller
I would kill for one person to say we need your big guy to me once in my life.
Andy McCullough
I'll explain that reference off the air. Mark said, the Big Guy is hanging them up. And I responded, allegedly. And he said, well, and then I said, you know, I hadn't heard anything definitive when I talked to 22 a couple weeks ago. And then he goes, what do you need from. I said. I said, what do you need from me? He said, dude, you are in Croatia. Aren't you about to fly? I said, no, we just finished dinner. And then he said, we need you, big guy, now.
Grant Brisby
Okay, I'm not going to make you do the whole text in Mark's voice, but you got to do the big guy part in Mark's voice.
Andy McCullough
Wow, Andy, we need you, big guy. And so, yeah, and so, yeah, I just wrote a little Gollum, just kind of ripping through, you know, his legacy with the Dodgers. Fabian Ardaya did a great job with the news story, which Came out very soon after Kershaw made the announcement. And Tyler Kepner wrote also something great about just the idea of, like, a quality. Like a. It was like high quality start. Like a quality start that's actually good, you know, Ye. There was like. I think it was like seven runs, or. Excuse me, seven innings, two runs.
Grant Brisby
Seven. Two. That's great. I love it. Yeah.
Andy McCullough
You know, which is kind of the standard that Kershaw has always set for himself is like, if I don't finish the seventh, like, I don't feel like I've pitched a good game. And so, yeah, you know, it seemed like he had a nice weekend, you know, at Dodger Stadium. The fans got a chance to, you know, sort of salute him. The team did. And, yeah, it's really just kind of like kind of putting a bow on the 2010s of baseball, which, obviously, you know, it's 20, 25. They ended a while ago. But I think, like, when I think about decade, which we've talked about a lot, just given our age and things like that, it's like the. Who are the players of that time? It's like, it's Clayton Kershaw, it's Mike Trout, you know, and who are the teams of that time? It's like it's the Giants and it's the Astros. Right. Like, those are the. When I think about that decade, those are the teams that. And the players that will come to mind. And I think he was, as I've said over and over, like the central figure of the 2010s postseasons for seven years. You know, the story was like, is Clayton Kershaw finally going to get over the hump? And that was a. You know, that's. That's a rare thing in the sport where one player can sort of, you know, be the focus of attention for such a significant portion of time. Yeah. And so just kind of, you know, putting. Putting a bow on that. You know, we'll see kind of how Mike Trout's career winds down. But, yeah, I don't really have much other than just kind of a weird last night in Dubrovnik.
Sam Miller
For me, the big three pitchers in that era were him and Scherzer and Verlander, all of whom are still sort of somewhat unlikely. Still. Still going up to now. And I feel like I understand why Scherzer is still going. You know, Scherzer's. He's such an extremely high wound extrovert that if he stops, I mean, asking Scherzer to quit is like asking a dog to like, give up the Frisbee. Like, it just. It doesn't seem likely. And then Verlander has clearly expressed, like, he has an interest in being an old pitcher. Like, he's expressed this desire for going back to, like, 2015, I think, is when he started talking about pitching until he was 45 or maybe beyond. And clearly he sees the challenges of being an old, effective pitcher as being like his. You know, that's his project. That's his quest, and it means something to him. Kershaw. I just don't really have an explanation for why he pitched this year. And it seems out of character. Like, it seems like he was ready to go years ago. It took a lot of labor to get back to this point. You know, I mean, he had. He had the injury. He had the shoulder injury. That's like a. Such a rough rehab, right? And he did that to come back to a team where he's no longer the central figure. You know, I mean, he wasn't even. He wasn't in the rotation really. I mean, barring something happening to one of the top five, he wasn't even necessarily going to be in the rotation. Some. Something did happen to one of the top five, so he started. But he's so family oriented. He doesn't ever seem like he's, like, enjoying himself.
Andy McCullough
I don't mean.
Sam Miller
And I don't mean that like in a. Like, in a cruel way, but like, he's. He's not drawing energy from the crowd or from the performance, from being a celebrity in any way. In fact, it often feels quite uncomfortable to him. And so I will always wonder, like, why. Why this year? Why did it exist? Why did we. Why were we Blessed with the 10 and 2 Clayton Kershaw swan song season when by all rights, he should have probably, you know, he. He probably should have been expected to walk away after 2024. So do you have anything you can.
Andy McCullough
Tell us not to hawk the book? I mean, in the last chapter of the book about Kershaw, you know, it starts at the end of the 2023 season and, you know, the World Series was in Dallas. So it just so happened I was there, you know, covering the World Series. And so I went to Kershaw's house before game one, and I, during the course of the project, you know, like, we talked a lot. It was just the conversation we had after 2023 felt very different. He felt way more sort of jumbled and I think unsure of, like, what exactly he wanted the rest of his life to look like. And I Think the book, you know, that's the chapter I'm probably like, the most proud of because there's, like. There's like, some kind of wild stuff in there, you know, like, he's like, on the record, says, like, I want to go play for the Texas Rangers. Like, I want to leave Los Angeles. Like, I am really frustrated with how things are going here in L. A. Like, he was, you know, open about kind of how he felt disconnected from, you know, his teammates, and he was just kind of unsure of, like, what his purpose was. You know, he was, like, open about how his. His faith, which has been such an animating part of his life, he had become disconnected in some ways from that, you know, and I think. So if you go back to that, you know, he had to have a lot of both, like, sort of internal machinations and also dialogue, you know, with his wife, of thinking about, like, just kind of what he wanted from his life, you know, what he was looking for. And, you know, he really came to the conclusion that, like, he still loved the sport, which I know is like, a cliched thing, right? Like, to be like, oh, I actually still really do enjoying this. But he is more. More so than Scherzer, certainly more so than Verlander. He is fairly tortured about the whole thing. You know, like, he's very open about how much he misses his family. He's struggles really to give up control. And, you know, missing events with his kids really weighed on him, especially given, you know, his childhood where his father was not particularly present. And so all this is to say is, like, when he decided at the end, in the winter of 2023, that he wanted to have shoulder surgery, that he didn't want to walk away, that he. He wanted to still do this. You know, he was committed to getting one more run, essentially just doing one more time and really enjoying it as best as he can, both for himself, for his family. And so, you know, there was a few changes that, like, he made one, you know, it ended up the Rangers and the didn't show as much interest as the Dodgers did, and he ended up going back to the Dodgers, which I think all parties are pretty thrilled about how that worked out, right. In 2024 last year, he moved out of the place where he and his wife and their kids had lived for a long time, and they all basically moved to the beach. They moved to Manhattan beach and lived on the water, which is, like, something that he had always kind of thought would be, like, a cool thing to do, but he didn't want to add 10 minutes of travel, driving to the ballpark because he was so obsessed with that. And he's like, he's like waking up every morning on the beach with his kids, like, drinking coffee, and he's like, I'm a dummy. Like, I should have done this years ago, you know, like. And so he just started to like, let go a little bit of some of the reins and just let like the light in and found that he like really did enjoy it, you know, and he like, wasn't really a factor in the postseason last year because his, his foot broke down. And so he, you know, just kind of had to sit on the sidelines and try and enjoy being a part of it. And he really did, you know, do that. And I talked to him during that process and he was like, I just want one more run. Like, I just want one more season where I can go out there and do this and, you know, get a chance to just say goodbye, like to just enjoy this one more time. And that's what this year was. You know, they lived on the beach again. His oldest son, Charlie, was like by his side most of the summer. Charlie's got a locker right next to him, you know, in the clubhouse, which was not a thing you would have seen in like 2018, you know, at Dodger Stadium. And so, yeah, I think it was like, you know, again, if you go back to that last chapter, like he's a. Of the book. Like, he's a very sort of like jumbled guy, kind of trying to sort things out. And I think in these last two years, he really has sorted out a way to author. Not a perfect ending, but something that can be satisfying. Does that make sense?
Sam Miller
It makes sense. It's. It's still a weird line to follow. I. I don't know. I guess I still have a hard time seeing how this was the satisfying year. I'm surprised that he didn't walk away before and I'm surprised that he is walking away now. It feels like a weird like in between, but God bless him for it. What do you mean by. In 2018 you wouldn't have seen Charlie having a locker?
Andy McCullough
Well, I think he was like 2 years old, so that wouldn't have made sense.
Grant Brisby
But more two year olds in locker room.
Andy McCullough
Yeah, right, right. It's like, no, Drake Laroche is not allowed in this room. Farewell 2010's baseball. We miss you. But I think it was because he was just so. Like when he wok up when he went to the ballpark, like that was Work and there was a divide. And when he was at home, he was home and he was dad and he was a husband, you know, and all those sort of things. But when he was at the park, like, it was work. And that was something that he felt was necessary in order to be who he was. Because he was always, for lack of a better term, afraid that if he did not do that, if he did not hold himself by this insane sort of standard, that when he got on the mound, he would not be the person that he believed that he needed to be. And I think in the past couple years, as he's like, just eased off that it's sort of like, oh, I, I like this. This is fun, you know, and so all of that basically, like, because he's not. He wasn't going to walk away after 2022, you know, when they get knocked out. And he pitched well pretty much all season, you know, and he was still healthy. Like it was like the first time. He wasn't rehabbing. He didn't want to walk away after 2023, you know, after just getting his brains beat in by the Diamondbacks and, you know, he decided to get shoulder surgery. And then he wanted to come back last year because he didn't really get a chance to, you know, to do it. And so this is the chance to do it one last time.
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Sam Miller
I mean, it's a complicated decision. So I could make a case for after 2022. I could make a case for after 2023. After 2024.
Andy McCullough
Sorry, just to interrupt real quick. Like, part of the thing is that, like, okay, you can. You can make a case for all that, and I think I can, too. And like, I've said I've made the case to him. Like, well, why don't you just, you know, like, what do you have to prove? And he's. And sometimes he's like, dude, I'm 35. Like, my life's not over. Like, I'm still good at this. Like, if I can do it and I'm good at it. Like, why?
Sam Miller
What?
Andy McCullough
You know, and it's like, it reminds me of Andy Pettit when he had his last year before the last year with the. The Yankees. He was asked at, like, his opening press conference that spring, some question. It was. It was kind of seemed like a silly question, but it, like, it animated him so much. It was from Pat Borsi and he was like, andy, do you think a man's purpose is to provide for his family? And Pettit was just like, yeah, man's gotta work. You know, like a man supposed to go to work, you know? And there is some of that where it's like, you talk to retired guys and they're just like, I do nothing all day. They feel adrift. And I think if you have. If you have been playing for a long time and you have friends who are in that mode, you're like, I don't want to just feel lost every day.
Sam Miller
Do each of you root for him to get into a postseason game, or do each of you dread the possibility that he actually goes out on one more, you know, game, game turning home run?
Grant Brisby
I. I would not be opposed to. To watching him do like a 2012 Tim Lincecum where all of a sudden he's like, super bullpen ace.
Sam Miller
Oh, no, Grant, you don't get to choose that. He's good.
Grant Brisby
No, he's good.
Sam Miller
The whole point of this is that we have come to believe that he will not be good, that he will not be 2012 Tim Lintigum bullpen ace.
Grant Brisby
Then that would also be funny and work for my purposes. So you can see how it's win.
Andy McCullough
Win for me, I would say. I think he very much wants to pitch, and so I'd like to see him pitch.
Sam Miller
In a way, it would have been very satisfying for me to see him retire after the 2023 postseason appearance. I have always found it in a weird way, I have found Clayton Kershaw reassuring. Because the lesson of Clayton Kershaw is that, you know, no matter how good you get, you're never safe. You're never safe from disaster.
Andy McCullough
Game always wins.
Sam Miller
That's a good reminder. Like, we all need. We all need reminders that, like, we're never going to get good enough, rich enough, accomplished enough that we feel secure. And to see Clayton Kershaw struggle in the postseason has it. I think it's like, a really positive message in my life. So in that sense, I'm not looking for him to have the fairy tale postseason moment. I kind of like that the negative ones were always there for me to learn from.
Grant Brisby
That's fair. That's fair. And I will say that when you're. When you were talking about Kershaw being able to separate and he had to separate, Home is home. Work is work. Right now, here's why I can't relate to that. Imagine him on the mound. He's going. He's trying to get the last out of the eighth inning. He's got the sign. He takes a step back, and then he hears, hey, dad, we're out of milk. Right? Because that's my life. That's my life. Okay? When I'm about ready to uncork that perfect lead, I'm asked about milk. So I can't relate. But I mean, honestly, I guess this just leads to the most important question before we switch to current events and stuff. Are there book plates still available?
Sam Miller
Yes.
Grant Brisby
Yes, please.
Andy McCullough
Thousands of copies of books are available and book plates. Send me an email.
Sam Miller
Yeah.
Grant Brisby
All right.
Andy McCullough
It's.
Grant Brisby
Why are you shaking your head? We gotta find it. It's your book. It's your book. It's a good book. It's a good book, people. All right. We have to care about either the Reds or the Guardians right now. Son of a.
Sam Miller
Yes, I see your frustration. We had this. We both. We shared this frustration last week, and I am now going to say that I was wrong. I've been severely wrong about three things this year. One was that Christopher Sanchez was not going to get better. One is that the Dodgers were. Everything was going swimmingly. Don't look at the record. And now the third was that a bunch of mediocre teams nursing large leads against even more mediocre teams would not make for an exciting September. And the last, like, six days have actually. They've been a plus. And right now we're in a good spot. They picked the right playoff format. It's pretty chaotic. The Reds and the Guardians, you know, I'm like. I'm rooting for them. You know, like, the bad teams are bad, the other bad teams are good. It makes for excitement. Yeah. I'm not mad that I have to care about the Reds and the Guardians right now.
Andy McCullough
I'm going to be perfectly honest about the Reds. I always kind of care about the Guardians, mostly because I just kind of know who their players are. So the postseason assignment I have is I'm going to be covering the brewers for as long as they go. And so the way it's setting up is if the Reds, I think, are the six, they could play the brewers if they beat the Dodgers. Right. And my stance on the Reds is I will find out who is on that team when they show up in Milwaukee for the workout day. And until then, they've got Ellie De La Cruz, they've got Andrew Abbott, Ryan Ludwig on the team. I don't know. Like, we'll find out.
Sam Miller
Pokey Reese.
Andy McCullough
Barry Larkin's probably still in the organization. I'll find that out.
Sam Miller
How?
Andy McCullough
Morris, I don't mean to be rude. Don't mean to be rude to the Castellini family. You know, Nick Krall, Terry Francone is the manager. I knew that. I knew that before this second.
Grant Brisby
Do you think J. Bruce has. J. Bruce is gonna hit in the middle of the order for the postseason?
Andy McCullough
Yeah. I mean, you know, Matt Leitos could come in and. Really, who knows?
Sam Miller
Yeah.
Grant Brisby
Seaver, famously, the only team he ever played for is the Reds.
Andy McCullough
Yeah. So that's my stance. Don't mean to be rude, but you just. A man must have a code. That's where I'm at on that.
Sam Miller
The main story of this race, I think, like, good, go, go, Reds, Go, Guardians, whatever. I do think, though, that mostly we're going to remember this race and mostly we're interested in this race because the Tigers and the Mets are really melting down. And maybe the Astros get thrown in there too. Well, yeah, the Astros get thrown in there too, which has. It took them. The Guardians, they've done their part. The Reds, they've done their part. But really the Mets and the Tigers understood the assignment. They showed up and they lost every game until it got closer. I've heard a lot of different words to describe the Mets and or the Tigers. I've seen choke. I've seen collapse, free fall, the bed spiral, meltdown, face plant, fall apart. Are all these just 100% synonyms for each other, or is there a distinction between the types of failure that the Tigers and the Mets are having? Are they distinct from each other? Do they require different vocabulary?
Andy McCullough
I think choke is strong because choke is like the God tier. Right. You can't do anything worse than choke.
Sam Miller
In my opinion, because it's a moral component.
Andy McCullough
Correct.
Sam Miller
Right. Choke is. You just. You were never a good enough person to succeed.
Grant Brisby
And it feels like that is event specific more than the culmination of a longer story. Like an entire team's season. At least that's how I read it. It's more like the game's on the line. It's Ohtani versus Trout and it's the wbc. Right. Like that's a choking situation where, oh, they just lost the division by game. That's more pissing it away.
Andy McCullough
Reading Clockers by Richard Price.
Grant Brisby
Great book.
Andy McCullough
Great book. Yeah. Really fun. And he has a line that actually I wrote down because it's, it's. You can't criticize someone's heart for the failings of their body. And that's choking. I know. Feel comfortable with that now. Collapsing. Yeah, these. Brian, hit this. These motherfuckers are collapsing.
Grant Brisby
Imploding would be my. That's very imploding.
Andy McCullough
They're melting down. They are face planting. Like I, I just. Yeah. I don't know how. What my taxonomy would be of the other levels of it. I just know that choke is.
Sam Miller
I like collapse. I do like the visual image of the support just being knocked and the whole thing just drops to the ground.
Andy McCullough
The guy climbing Everest.
Sam Miller
There's a big difference though, because in the Mets and the Tigers I think, I think, think we would agree on this. You know, the Mets have been trying to be a contender. It's hard to explain why they're not better than they are, but it's not for lack of effort. Like, they invested in the team. They've got good players. And when they got to the trade deadline, they said, well, we've got some holes. Let's. They actually went pretty big on the bullpen. Like, they, like, yeah, they overpaid in some ways. It hasn't worked out. And you're like, wow, well, these players. This team is. Is bad after all. But the Tigers, on the other hand, they went into the trade deadline almost with an, like a sense of hubris that they didn't need to get any good players. I mean, the. It's almost like they went in the trade deadline and they said, make sure that everybody we get can be comfortably left off the postseason. And now, you know, like, they might.
Andy McCullough
All be left off the roster.
Sam Miller
There's a real sowing reaping situation going on with the Tigers, so I don't know that we can use the same word one way or another. Like, the Tigers maybe feel more like spiraling. Like, you know, when you fly too close to the sun and then the, the wings, the. You know, the. The wings melt, then you sort of like spiral back to earth, whereas the met are more collapsing. It's hard to understand what the cause of it was, but just something kicked the legs out from under them and they just sort of fell over.
Grant Brisby
I will still suggest, and this is just pure theory, this is pure speculation, fan fiction, whatever, that Scott Harris and the Tigers have a timeline in mind that is not necessarily inclusive of 2025.
Sam Miller
And it's been like, not inclusive, not inclusive. Like 2025 isn't even in the data set. That's the crazy for nothing.
Grant Brisby
That's the gravy, if you get it, baby.
Andy McCullough
That's the knows what the words actually mean. They have conducted themselves the last couple years as if either they think they are much better than we think they are or much worse. Their records suggest they are right. And it's like, we have a timeline. We're going to compete in 2026 and 2027 and we don't care. We're not mortgage and nothing until we get there.
Grant Brisby
They're waiting for the conveyor belt is what I feel like. They're waiting for just that constant churn of veterans and prospects and getting something sustainable. And that's when you start attacking the free agency. That's just my idea, and I don't think it's a bad idea. But when you get to a situation like this where you're ahead of schedule.
Sam Miller
And you don't think it's a bad idea. Look, if you envision a scenario, if you're real confident and you envision a scenario where you can just print money some years from now, then you should have faith that you will be able to make that work when it comes that you shouldn't be so scared of blowing some opportunity three years from now that you can't even look at the opportunity that's in front of you right now. Like, it would be a real sort of. Like it would be a weak view of your future to say, well, we have to hoard every possible thing because, you know, anything that we trade away now, that's the difference between 2028, failing or not. You know, they're really, they were really close. They are really close right now. You don't have to trade, you know, your three best prospects to get Andrew Miller. Who's in? Wait, who's that? Who's the overpay? Who's the bullpen overpay or Aldous Chapman? Was that the bullpen overpay?
Grant Brisby
Like the Kyle Finnegan for the Tigers?
Sam Miller
But no, no, I'm saying like, like a classic thing where like, yeah, it's team traits for. Yeah, you don't have to do that necessarily. But like.
Andy McCullough
Or you could. It worked out for the Cubs.
Sam Miller
Yeah, yeah, you. You could. That's true. You could. They won the World Series that year. Not because Araldis Chapman was so good, but whatever, it got him there.
Andy McCullough
Are you familiar with the butterfly effect?
Grant Brisby
Heathcliff Slocum? That's like the gold standard of overpaying for a closer.
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Andy McCullough
The whole thing with their timeline and their urgency. You know, Scott Harris said something when they did kind of, you know, effectively didn't really add many difference making players at the deadline. He said, I think the idea of a window is an illusion. And like look, I'm sympathetic to that general idea, right? You make plans, God laughs at them. But Tareks, Google is a free agent after next year. So you do have a window. Your window is when you employ Terry Skuble. That is what it is, man.
Sam Miller
The idea of a window is an illusion. So I look at that when I hear someone say that, I think that's a live now, live for the moment philosophy. Because the idea of the win. Traditionally baseball people, when they talk about windows, they're talking about like building a five year period where you can succeed consistently and therefore you push off the resources of today to build a five year window. And that's in contrast to like, hey, we're good right now. Maybe we should try to win the thing that's right in front of us. So I'm surprised that if he doesn't believe in windows, I'm surprised that he wouldn't think like, well, the only thing that's real is today. The only thing that we really have control of is the next breath and go for it right now.
Andy McCullough
That would be one way to interpret it, but they did less than that.
Sam Miller
Yeah, it sounds like window thinking is what I'm saying. It sounds like what he's describing is classic window.
Grant Brisby
And I would like to amend my statement saying it was a good plan. I was thinking more and I was speaking in his, the Tiger's voice. Like it's, it makes sense to them. In practice though, thinking about two years down the line in baseball is nonsense. It's, you know, if you've watched baseball for more than two years and you, you have to understand that you don't know what's going to happen in 2027. So live, live for the moment. That's my official podcast policy.
Andy McCullough
These guys get paid tons of money, right? And they are judged by their record. And when their record is good, we praise their processes. And when their record is bad, we say you should get different processes. And that is a probably a flawed way of evaluating this, but in America we have a saying and it is scoreboard baby.
Grant Brisby
That's an awful saying.
Andy McCullough
I am sympathetic to this because we all understand that spending on middle tier free agents is inefficient. And we all understand that at the deadline you are over leveraged to give up, you know, to lose deals in surplus value. But as Andrew Friedman said, and as I get retweeted every winter, if you are rational about every third every free agent, you will finish third on every free agent you know. And part of the job is understanding when is the time to hold the line and when is the time to be irrational. And if you aren't, if you hew towards the rationality and your team stops playing good, you're gonna get ripped for it is what it is.
Sam Miller
They are still in first place. They are 85 to make the playoffs according to Fangraphs. 3% to win the World Series probably. Let's see, they are two games behind the Mariners for having a first round buy. It is very conceivable that they simply win four of their next six. Nothing strange about that. And they end up with a first round buy and say, see, there was nothing else we could have done in the regular season. And you know, sometimes things work out that way. I won't begrudge them their success. I think though that there's. Baseball is so unpredictable that there are only two kind of timelines that really make any sense. One is there are always teams willing to overpay for now. And you can take advantage of those situations to win every trade in the future. You know, you can trade two wins now for 10 wins in the future pretty reliably as long as you know you're, you're comfortable living in the future. You know, you, you're comfortable always pushing off your good players into the future. But you like, you can win every trade if you're trading now for the future. So that's one way of doing it. And a team should have a balanced portfolio. Every team should be making some of those trades. And you know, obviously the Rays are like the classic example of a team that makes those trades and it's helped their, their organization be fairly perpetually contending. Okay, the other timeline that Makes sense is like the next four days, like anything beyond that. Baseball's too unpredictable. But like the next four days, we pretty much know who's good and who's bad and which games matter. Like, we know the leverage of this week is really high. You couldn't invest better than over the next week. So when you find yourself in that rare position where you're going into the playoffs, this is the team that you have that's actually good. You might never get another one, but this team is good. It's two months until October and you've got plenty to play for. That's a good time to overpay for now. And so you should, you know, probably like when the time is right, overpay for now and when the time is wrong, take advantage of some other team that's overpaying for now. And those are kind of the only two timelines that make any predictable sense in baseball. And when you are in the now and you're not playing for now, you know, like, that's hubris. That's like, that's where you end up getting into trouble. And if it goes wrong for you, we all sort of point and go, well, we said something about this in July.
Andy McCullough
Yeah, I mean, we, we talked about this team. We did a whole episode and we kind of came away being like, I don't. School's good.
Boland Branch Representative
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Andy McCullough
Yeah, McKinstry, you know, anyway, Sam, you mentioned just how much fun the last like six days or so. And you know, I remember like when I was a younger person, like reading Roger angel for the first time and, and you know, when he does the, that sort of like season wrap up, you know, the second as the post World Series one, he's always got like a few pages on just like him having a good time watching ball in September. He's just like, I turned on the radio and I was, you know, in Cape Cod and listened to my socks or whatever and you read that and you just like feel like almost envious because you're like, oh, this is great. Like, I would love to watch baseball. Then you turn it on. You're like, what the. These strikeouts. But I have that feeling going into this week, you know, like, I looked at the schedule today and there's three games and I legit was like, oh, come on. Like I, you know. Yeah, like, it's just, it's just an excitement of like, you know, just I'm going to sit back and like take it in. All these teams are. They have some great players and they all have Catastrophic flaws. And they're going to, like, you know, have some car crashes for the next few days. And who knows, who knows where it'll end up.
Sam Miller
I was watching the Astros Mariners. This was the high is a great weekend for ball. I enjoyed it, all of it. But the high point was definitely on Saturday when the Mariners won a big game against the Astros. Basically, well, they guaranteed that they were going to walk out of the series all alone in first place in the AL West. And I forget which play it was, but it was the game turned on a pretty big play late in the game or there was a pretty big play late in the game. And I was watching the Astros feed and it was like a very, like, you know, glum ish broadcast as the Astros lost the game. And you could hear shouting. And I thought, why? The field mic is picking up somebody maybe really angry in the dugout. And I was trying to figure out what is happening that is so angry, angry down there. And I realized that it was actually the Mariners broadcast bleeding from one booth to the next. And so you heard the Mariners broadcaster, Aaron Goldsmith, like, screaming with like, can you believe it's actually happening? While the Astros broadcast was like, and we'll be back with the pregame show at 6:40 tomorrow.
Andy McCullough
For Seattle. Just what an emphatic kicking, right? To just go into whatever they're calling Minute Maid park now, sweep them. The play by Robles to end Saturday night was wild. You grind through the season, right, and try and take joy out of it along the way. And then if you're lucky, you get rewarded. And I feel like this season's been kind of a grind. We've been fairly open about how just confusing it is, but. But yeah, it's like, it's very exciting right now. I feel really excited to watch some ball over the next five weeks.
Grant Brisby
I would say, as scripted excitement goes, like, if you're trying to script excitement late in the season, having a guy make a catch like Robles did after he missed most of the season for diving into the stands and hurting himself on a different catch. Like, having that guy back and then doing that is like up there with like, okay, that's cool. We're in. We're going to win it all this year. Like, right. It's hard to feel more confident at that point. Like, yes, the stars are aligning for.
Sam Miller
The Mariners right now, if I'm not mistaken. Even the. So the Blue Jays Yankees has gotten close enough that the winner of that's going to get a buy and the loser that's not. So that's real stakes. And then Detroit, Seattle or whatever, the division winner between the Central and the west is close enough that the second buy is up for grabs. The AL west itself is close enough that that division is up for grabs. Detroit, Cleveland is close enough that that division is up for grabs. And then you've got the wild card, which is Padres.
Grant Brisby
Dodgers is still up for grabs.
Sam Miller
Five teams within four teams within two games of each other. Within one game of each other. Four games with four teams within one game of each other for the last wild card spot. So, yeah. What's the one you said is Dodgers.
Grant Brisby
Padres.
Sam Miller
Yeah, Dodgers. Padres. Yeah. Well, the Dodgers will never fail. I. I feel pretty confident about it.
Grant Brisby
So are you saying that you have to hand it to Manfred.
Sam Miller
It's just ridiculous to ever get to a point in the baseball season where you're like, baseball sucks now. It'll never be good again. Like, you just gotta not. You gotta like, no, it's coming back. It's coming back every time.
Andy McCullough
The best advertisement for baseball is baseball, right? Like, it's a good time, it's a good game. It requires a lot, I think, to be really enjoyed. And I think that's why it's probably one of a. One of not to get too deep into it. But, like, one of the reasons why it has probably lost some cultural purpose is that you really got to be into it. To be into it, I think, because you don't get the rewards without suffering through all of it. But, yeah, like, this is. I don't know. It's like, it's. There's sometimes where I go into October where I'm just sort of, like, worn out and like. All right, let's just get. Can we just fast forward to Dodgers, Astros, too. You know, like, I've been. There's been some years like that, and this time it's like, who in God's name is going to win the World Series? Like, who it's going to win? Like, I guess, you know, the Philly. Whoever wins the Phillies Dodgers series, if they ever. If they play in the ds, who knows?
Sam Miller
This is not what the show is about. This is not the topic. But I. The you have to be into it to be into it theory for why baseball has lost cultural relevance is an interesting theory, but doesn't it seem like all evidence from pop culture in the last, like, decade, like, fan culture points the opposite way that, like, nowadays, to enjoy a single Marvel movie, you have to have seen, like, 25 other Marvel movies, and people like their TV shows, not as a TV show that they spend an hour on, but as hours and hours that they spend, you know, thinking about, reading about, you know, discussing. And I mean, I could give 50 more examples, but I mean, just political hobbyism, like, the amount of time people want to spend on things that, you know, they consume actually feels like it's gone the other way. Everybody's rabbit holed. And so why doesn't baseball get the rabbit hole boost?
Andy McCullough
Well, probably just because there's so many rabbit holes now.
Grant Brisby
Yeah, that's. It's spread so thin, but, like, everyone's doing diving into a rabbit hole. That's why we're even here talking.
Andy McCullough
It's like if someone asked me a question about wrestling and I'm sort of nervous about answering it because it's like they're either gonna be really into this or they're gonna think I'm a crazy person, you know, and so, I don't know. I think there's a lot of topics where, you know, like, you can go, yeah, there's just more available now with like, the Internet and everything. So. And I. When I think about sports consumption, like, like what animates people, it feels very much like, you know, football is king because there's, you know, they play on Sundays. Right. But also you can atomize it to like, your fantasy team or, you know, your survivor pool. So there's only one real, you know, it's just, it just gets smaller and smaller and you can take really big bites. Whereas in baseball, you just can't get too invested on what's happening on a Wednesday night. That's no way to go through life. Certainly that'll. That'll drive you crazy.
Grant Brisby
I will say at minute 45 that this is a super interesting conversation. Want to take it like another hour? But I. One, one thing I wrote a long time ago, watching Giancarlo Stanton take batting practice is that when you go to see you, you've plunked down your hard earned money. You're going to see Steph Curry. You're taking your kid. This is the first game to see Steph Curry. Steph Curry might have an off night. Goes 1 for 11 in three points, right? Just a terrible night. But guess what? He hit a three pointer. He hoisted up. You were like, this is what I'm here to see. And he did it. He did it right there. You can go a month without seeing Kyle Schwaber hit a home run. Practically a month. Like Cal Raleigh can go a couple of weeks without that. It's just a different sport. You're guaranteed to see big guy make dunk in basketball, more or less anytime you watch that big guy. Whereas baseball ebbs and flows. It takes a little bit more patience, even in the context of rabbit holes.
Sam Miller
Yeah, true.
Andy McCullough
Hey, before we go, I just want to say one thing related to the Tigers. Sam was right about Jack Flaherty. I was wrong.
Sam Miller
You've already done that. You've already. I appreciate you.
Andy McCullough
I'm just gonna keep saying it.
Grant Brisby
I haven't checked back in with Javi Baez since I said he was back. I'm just gonna assume he's back.
Sam Miller
Mvp, I think everybody's talking about who's the mvp. Cal Raleigh, Aaron Judge, or Javi Baez.
Grant Brisby
Yes. So I'm not apologizing to nobody. I was right back then. Still right. All right, we'll be back on Friday. We'll have more information. It's so funny to think like, Friday's soon, right? To me, that's like our next podcast. It's coming right up. There's gonna be so much that happens, so much chaos. I love it. All right, we'll be back on Friday. See you then.
Andy McCullough
I was very wrong.
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Sam Miller
If.
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Episode 178 | September 22, 2025
With Grant Brisbee, Sam Miller & Andy McCullough
This episode of The Windup dives deep into the seismic news of Clayton Kershaw's retirement, explores his complex and legendary legacy, and then pivots to the thrilling chaos of the MLB playoff races with just a week left in the season. The conversation blends personal insights, humor, and baseball philosophy, led by some of the sport’s sharpest minds.
[02:57–15:16]
Notable Quotes
[15:46–20:49]
[21:11–27:43]
[27:19–34:37]
[37:29–45:43]
[45:43–46:31]
“He is more...fairly tortured about the whole thing...like, he's very open about how much he misses his family. He struggles really to give up control.”
— Andy McCullough on Kershaw’s last years, [09:45]
“The lesson of Clayton Kershaw is that, you know, no matter how good you get, you're never safe. You're never safe from disaster.”
— Sam Miller, reflecting on the meaning of Kershaw’s postseason struggles and their universality, [19:19]
“The best advertisement for baseball is baseball.”
— Andy McCullough, on the sport’s unique rewards and challenges, [42:00]
“There are only two kind of timelines that really make any sense…one is…you can win every trade if you’re trading now for the future…the other timeline…is like the next four days…when you find yourself in that rare position where you’re going into the playoffs, this is the team that you have that’s actually good…that’s a good time to overpay for now.”
— Sam Miller, on team-building philosophy, [36:05]
This roundtable is an essential listen (or read) for anyone invested in baseball’s past, present, and future. It’s part eulogy for an era (through Kershaw), part celebration of the sport’s postseason drama, and part critique of how modern front offices weigh the risk and reward of “playing for now.” The blend of insight, storytelling, and self-aware humor makes The Windup’s roundtable format a must for baseball fans.