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Baseball Isn’t Boring

BIB Vault: What It's Like For A GM At The Winter Meetings

29 Nov 2025

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: What insights does J.P. Ricciardi share about preparing for the Winter Meetings?

0.031 - 3.094 J.P. Ricciardi

Yeah, there should be some passion. This doesn't have to be boring.

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3.294 - 11.802 Rob Bradford

Hey, one thing the game needs is more people like you. Do I have grown men run around tight pants?

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11.822 - 25.334 J.P. Ricciardi

It's Mookie Betts. It's Daniel Bard. It's Steve Aoki. It's Sal Tlamacchia. This is Brock Holt. Hey, this is John Lester. Baseball isn't boring. Baseball isn't boring. Welcome to Baseball Isn't Boring. Here's your host, Rob Radford.

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There's no human being I'd rather be talking to right now than J.P. Ricciardi, podcaster. I mean, podcaster. Congratulations on, you know, I feel like much like you helped me getting in the book writing business, I helped you like basically pave the way for your podcasting excellence. You introduced me to the dark side. It did. But you're good at it. You're good at it. So I appreciate it.

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It's a lot of fun. It's like, you know, when you're talking baseball with guys you like, how can it not be fun? You know, it's actually what I miss the most about not being in the ballparks is, you know, talking to all the writers that you used to run into, talking to the baseball people, talking to the scouts. And I know that doesn't happen too much where scouts are against anymore.

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But, man, it's just I feel like we've lost that part of baseball. And this is a nice way to kind of connect with it. But I feel like, JP, even so, you did your first podcast here on this one. And it's funny because sometimes people don't really get it, like how awesome this medium can be because of exactly that. When you did it, it's like we're just having a conversation, right?

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It's not segmented. And I remember, JP, Mookie Betts obviously has his podcast now. And he talked about all he knew was sitting in front of his locker, answering questions, just trying to get it over with, whatever it is. And all of a sudden, now we had to start listening. Now we had to start talking, and it was okay, you know? So, yeah.

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Well, I think when you're, you know, in my case as a general manager, any kind of front office executive, you've got to be a little guarded about what you can say. You know, I got in trouble a few times because I let my guard down and said what I was really thinking, which it's unfortunate you really can't do that.

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Um, but I think from a player standpoint, they're so guarded as to what they can and can't say and what they really want to say. It is, it is tough for them. And it's nice when they get on the other side of the microphone because they probably sit there and say, man, I, I could have been a better interview if I, I let my guard down a little bit. I'm telling you, again, come back to Mookie.

Chapter 2: How does a front office executive navigate the complexities of trade discussions?

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When I try to tell this, I've told this to executives, I say, listen, tell me if I'm wrong, like, tell me if I'm wrong. Right. But I feel like even even like if we had a good relationship and you were a GM and I was wrong about something, most of the time, the executives don't tell me. even like the writers they get along with that they're wrong.

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And the reasoning I think they'll say is that, oh, this is too much. It is what it is. It doesn't matter, whatever. But still, I mean, once in a while they will. I mean, how did you handle that? I'll give you a perfect example. One time we're at the GM meetings and there's one writer from Toronto, one writer. And we're getting ready to sign Frank Thomas to a two-year deal.

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We come to terms with Thomas. The writer can't be found. He's not even around. So I told my assistant at the time, I said, call so-and-so. Tell him we're going to sign Frank Thomas. I said, he's the only writer here. He's going to get in so much trouble if he doesn't have this scoop. I said, so tell him to come back to the hotel, and we'll tell him what we did.

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So trying to be a nice guy and trying to realize the guy's job was not jeopardy, but that's why they sent him to the winter meetings. And if this story broke and he didn't have it, That is definitely an aberration. I just felt bad for the guy. But let me tell you, they don't reciprocate that. But how about the times where they're wrong? I mean, where there's more than one writer.

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You know what I found? Yeah, go ahead. Yeah, but this is what I found. I found the really good guys you could have these conversations with. You could say to them, look, I read your article. This is what you said. This is why we can't do this. This is what's happening.

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I can't tell you that in the public because if you write that, then I'm going to get in trouble with, you know, that's my dog, Bruno. I'm going to get in trouble with the people I have to answer to. But I'm trying to create a really good dialogue and a friendship here. I'm trying to explain to you why I can't do this. Hopefully you won't run with this and write it. And I think...

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Like Toronto, it didn't work because some of the writers in Toronto just didn't get it. They just had an agenda that they were going to not like someone. They would say, we're not going to like this guy. We're not going to take the time to get to know him. But I found with the other guys that you spent time with, it was great. Well...

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Correct me if you think differently, but why don't executives do that more? JP, I just say, listen, I am trying to be right, but maybe I'm misguided. Here's an example. I think it was last year, maybe around the, I don't know when it was, but it was, I said, an agent told me a team was interested in a player amongst some other teams. So I said, this guy is drawing interest from these teams.

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The GM from – actually, the GM that you know very well, who – he texted me. He's like, that's not true. We have no – we haven't contacted at all. And I said, I appreciate that. But that happens so – maybe I'm right all the time. I don't know. But it's – but you know what I'm saying? Like, this doesn't happen all the time. I think –

Chapter 3: What role does media play in the dynamics of the Winter Meetings?

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He was great. He made the all-star team. He played hard. He didn't, you know... He didn't go outside the lines. He was great. So that was a case where we took a chance on a guy and it ended up being okay. The second year was miserable, but his true personality came out at that point. And I don't think Shea's a bad guy. He was dealing with some things.

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But we knew going in that this was a guy that had had some problems in the past. So At least we knew. If I make that decision, I made that decision knowing it. So I think having those relationships goes a long way. Yeah. I mean, I remember conversations that we've had I remember – and some of the popular – like, Curtis Granderson. I remember you saying, like, what a – you know, this guy.

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You know, like, what kind of guy he is. You know, and how that – maybe he's on the other side of his prime years, but still, like, the fit that he's going to have. You have to take personalities. Like, I know you have Papelbon on your show a lot, right? Yeah. And Papelbon's the kind of guy, when you're sitting in the other dugout, you want to rip his head off.

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But when he's on your team, he's the greatest teammate you could have. So when you look at a guy like Papelbon and you know that's how he's wired, you know that I'm either bringing this guy in because I'm attracted to that and what he brings to us, or you say, I don't want that type of guy and I back away. Now, personally, I hated Papelbon because he was so good against us. Yeah.

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But he's the kind of guy that if I had a chance, he'd be the first guy I'd want pitching out of my bullpen. And he was made for Boston because he had that mentality that he could pitch in Boston. I'd take a million papal bonds if I could find him on my team. But you know what his personality is like. So you have to realize or decide. Do I bring him in or do I not bring him in?

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And, you know, those are the things that you have to weigh as a general manager. Yeah, and you have to ask around. I mean, I'll give you another example. The guy who owns the LLC for this podcast, Joe Kelly. You know, Joe, he's not getting signed by the Yankees right now because he's ripped the Yankees 50 times since the World Series. But...

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You tell me a time where Joe has ever said a bad word about any of his teammates, including, by the way, the most dysfunctional White Sox team in the history of baseball, you know, which he was on. And so, yeah, I mean, is he good for your team? Is he good for your clubhouse? But, you know, I just... When you're talking about relationships, JP, it is so true.

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And again, I don't want to be like old man yelling at clouds, but it's true. It's true. It's so true. I don't understand. It doesn't matter. If you have a problem with your car, don't you go to a mechanic that you like, that you've had a relationship with? If someone said, hey, I need to put a new roof on my house, who do they recommend that you know and you can trust?

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I don't think life is any different than baseball. I just think we've been so... And we've become so callous in our game by the people that are now, not all of them, but a lot of people that are running organizations now, they don't cultivate relationships. It's like, I'm going to be here. I'm in my ivory tower. I'm not going to talk to my scouts.

Chapter 4: How do GMs build relationships within the baseball community?

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I like what Brian Cashman has done with Nehring. Well, Nehring is excellent, but he's also got Brian Sabian, a Hall of Famer. And he's got Omar Minaya, who... has a whole different mindset. So I think some of the teams that have brought in some veteran guys, and I think it takes those guys that aren't threatened by those guys. That's a big part of it too.

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They have to really say, hey, I want Gene Katie sitting on my bench if I'm the head coach at St. John's. I want Bobby Knight with all his experience sitting aside of me because they've kind of lost their drive to be what they once were and they just want to contribute. This is the first Gene Katie reference on baseball isn't boring officially. I remember he went back and helped Lavin over at St.

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John's. Sure. Listen, Pete Carrillo goes to Sacramento, you know, assistant in the NBA. Ralph Willard was a great coach at Holy Cross and he went over and helped Patino. So I think there's something to be said for having experience around you. And, um, Like I said, it goes back to what we were talking about, all having relationships. Yeah.

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So to pivot to the winter meetings, one part of the winter meetings, and I think you can add insight better than I can. So you go up to the suite. You've got a suite, right? Yeah. It's usually like an unbelievable pit mass by the end of it, I would imagine, right? It's like a frat house. It looks like animal house. So you have your people up there.

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You also send, correct me if I'm wrong, but you also have people you send go down the lobby. Yeah. Go down the lobby. It's such a weird dynamic. Go down the lobby and talk to people, see what people are saying, what's going on. Yeah, so that is a dynamic, right? I got some great – Oh, come on. Let's go. I love stories.

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Some of the funniest things have happened at the – So one time I'm coming out of the – My suite. And the reason GMs don't come in the lobby is because they get hounded mostly by people who want jobs. And I'm sympathetic to those guys. But a woman comes up to me. She says, you got two minutes? I said, well, you know what it's like. So I said, we're going to dinner.

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I said, just walk with me and tell me what you. She goes, well, I'm a psychic.

1190.647 - 1209.468 Rob Bradford

What's good, y'all? It's Von Miller, Super Bowl MVP, SAG Master, and now your host of Free Range. This is where NFL meets real talk every week. I'm bringing you inside the game from locker room stories to league-wide headlines. You want football IQ, locker room insight, and real conversations with the people shaping the league?

1209.488 - 1220.4 Rob Bradford

Welcome to Free Range with Von Miller, where nothing is off limits and every down counts. New episodes every Wednesday. Listen and follow Free Range with me, Von Miller, wherever you get your podcasts.

Chapter 5: What strategies do teams use to approach player negotiations?

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His tie's down here. He looks like Pete Carell on the sidelines. He's all disheveled. His notes are all over the place. So I'm going by. I go, hey, buddy, how you doing? He says... Oh, not too good. I said, what's the matter? He goes, wow, this is a tough racket. I said, yeah. I said, it's not easy. He goes, would you mind looking at my resume? So I said, yeah, yeah.

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Come on, just take a walk with me. So we're walking out. I'm looking at his resume. I go, what job are you looking for? He goes, I'm looking for any entry level job. He goes, you guys have one in Toronto. I says, you know that job pays $15,000? He goes, yeah. He goes, I want it. So I'm looking. I go, you went to the Wharton School at Penn? He goes, yeah.

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I go, what are your parents going to say if you took a $15,000 job? And I felt so bad for the kid, but I should have followed up. He might be running a team right now. I know. I was going to say. I got no idea. I was going to say.

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Oh, he is. But so you have that dynamic. And then so as you say, like in these days leading up to what it is, you know, the whatever, we're five days out, four days out, three days out, whatever it is. Are you saying, okay, this is what I want to get done when I get to the winter meetings? Well, I don't think it's a matter of what you want to get done.

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I think it's like, how do we address our needs? And then you've had conversations with, say, Texas or Minnesota or the Cardinal. You're having these conversations, and usually it's like, okay, let's talk at the winter meetings. Let's talk at the winter. Baseball is a game of deadlines. For some reason, it's like the only thing that makes it move is deadlines. Well, yeah.

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Well, I was going to say it used to be a game of deadlines. Yeah. Well, still stuff happens more so at the, at the winter meetings. Right. It is getting pushed further back. I get that, but it would always be, you know, you'd set up these meetings and you'd go in and, and some guys were just great. I love dealing with Dombrowski. He was great. I love dealing with Sherholtz. He was great.

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Sabian was great. Um, But this is usually – maybe it changed, but it's not like they're going suite to suite, right? We used to go suite to suite. Did you? But now it's all texting. Yeah. Do you want to meet? You know, this and that. So anyway, but usually you're doing all your work pre-winter meetings and trying to – So we were always very aggressive because we didn't have a lot of money.

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So we had to get stuff done fast because we didn't really want to be left with just the leftovers. What we wanted to do was at the end, if there was something good, like one year we got Benji Molina, he fell in our lap and he fell in our lap because I had a good relationship with his agent. Imagine that, you know, we got Scott Downs because I had a good relationship with his agent.

Chapter 6: How has social media changed the landscape for baseball executives?

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Okay. I'll go back up. And, you know, that's how we got, uh, when I was in New York, that's how we got, um, Oh, the kid who played for the pirates switch hitter, second baseman, uh, Anyway, it was in the lobby. Roy Smith heard that the Pirates wanted to move him, and they wanted our left-hander at the time. I can't remember him either. We ended up – Sandy was sick.

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So John Rico and myself were the GM, and we ended up pulling off the trade. So we'd call Sandy and say, Sandy, hey, Pittsburgh, boom, boom, boom, boom, boom. He said, go ahead. And then I ran – that same year, I ran into – uh, Alan Nero's group and, uh, Scotty, uh, Scotty Pacino. And I was good friends with those guys. And they said, uh, you got any interest in his Drupal Cabrera?

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I said, I love his Drupal Cabrera. He goes, he's getting ready to sign with the Braves. I said, hold on a second. I called Sandy. I said, Sandy, this guy can really help us. He can hit, he can play 30, he can play short, he can play second, he can play first. He's a switch hitter. He could do a lot of things for us. I said, uh, He's going to go to the Braves.

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But I said, I think if we do the boom, boom, boom, boom, boom. So Sandy says, okay, pursue it. So I called Scott. He said, what's it going to take? He says this. I called Sandy. I said, Sandy, give him a two-year deal. Boom. And we got it done. And he was great for us. He was absolutely great for us. You know, that's how it works.

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You know, so when it comes to actually getting stuff done, the winter meetings, unfortunately, in recent years, so they have a stage set up, right? They have a stage set up and the stage has always been, there's going to be a trade.

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There's going to be a signing usually along with some other stuff, but usually it's for the trades and signings and JP, like in the last few years, that stage has been empty. There has been very little things, but I always remember for some reason, you know, we have this images of moments where that stage is used. And for me, it was the BJ Ryan, AJ Burnett,

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I mean, both those were at the winter meetings, right? Back-to-back press conferences, pretty much, right? Well, that's when they gave us some money and we could do some things. And, you know, we had to overpay to get those guys. But we got them, you know, because we said, hey, listen, we got to take a shot. And actually... I think we were one of the first teams to give an out to a player.

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Really? An out. That's another funny story. After we signed Burnett, we give him a five-year deal with an out after three because my whole thought process was, listen, if he's good for us for three years, that's great. He wasn't going to come here anyway, so we had to do something to get him. We had to be creative to get him to come to Toronto.

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So we go to a season ticket holder event in the winter, and there's probably 1,000 fans there. And you're sitting up there all by yourself. And, you know, a thousand fans. So they pass the mic around. Guy raises his hand. He's in the back. And he says, I can't believe you gave A.J. Burnett a five-year deal. How could you do that?

Chapter 7: What are the challenges of signing high-profile players like Juan Soto?

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It was heavy fog. You couldn't see the skyline. And I'm driving them and I'm trying to tell them how great New York is and how great the city is. And I can't even say like, oh, look at the skyline. And I'm like, oh, this is just disaster. You know, got to get the umbrella for his wife to come off the airplane. It's pouring.

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And I just told Sandy, I said, JP, could you believe we were talking about this lately because of the soda stuff. But like, obviously the Blue Jays, they're the team that showed, hey, we're willing to spend $700 million. Good for them. But they also had gone through this sort of recruiting process last year.

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And it's so bizarre to me that we look back, and part of the recruiting process was bringing the guy to Dunedin. It was bringing Otani to Dunedin. Well, I think they put so much money into that complex, they wanted to show him. But man, talk about a great city, Toronto. Why wouldn't you bring him to Toronto? I know, I know.

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well it's uh yeah so the last thing is is if you if put if you were in this situation like with just say i know it's every gm's dream to be in that situation with to have the money the owners say oh yeah you can you can make a legitimate pitch to soto what would you what would you do Well, I think, first of all, you have to look at the player, right?

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I never saw Ted Williams play, but this guy has to be the most comparable guy, I think, as a left-hander hitter to Ted Williams because of his unbelievable command of the strike zone. And he's got power. He can hit. He's a complete offensive player. So you're going to get an amazing offensive player. It just comes down to the reality of when you sit down and say –

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This guy's getting $700 million. 15 years ago, franchises were selling for that. So I'm just trying to get my head around that number and think, okay, what else can I do besides bring Soto in? And I think the four teams that are involved, if I had to handicap this, the way I would look at it is – The Red Sox are trying to make a big splash, so they're going to be involved.

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The Mets, I think, want to make an even bigger splash because they came so close. Cohen's got a Latin American wife. They've got a heavy Latin American team, and I think it's a great community for Latin America. The Latin Americans love the Mets in New York. That's a selling point.

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Then you've got the Blue Jays, who I think are the outlier, and the only way he goes to Toronto, to me, is if they check absolutely at the last dollar. Yeah. I don't see the draw for Toronto for him. I mean, it's not historical. It's out of the country. Also, and the foundation of the team, you don't know. They can say, hey, we're going to sign Vlad Guerrero Jr., but they don't have him signed.

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They don't really have that group together. Their farm system's not good. They're not going to be good going forward. He'll make them a great team. He'll make a great player on a team. But like you said, are they going to be able to sign Bichette? Are they going to be able to sign Guerrero? No, maybe they can. I don't know. But I think Toronto would be four.

Chapter 8: What humorous anecdotes does J.P. share from his experiences at the Winter Meetings?

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I don't know Soto at all. I just, I love him as a player. I don't know him as a person. So I don't know what's, what's near and dear to him. And look, when you got $700 million, you can make any place, you know, the best place in the world you want to be. But I do think, you know, winning's important and, uh,

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I'm really curious to see how it plays out in Boston because it sounds like they're very, very serious, and I just don't know if it's going to be the last dollar for Soto. Boston's an attractive place in a lot of ways. Yeah, but you've got to go back to the shock and awe Red Sox. JP, you know, I can name two times before Dabrowski left that they lost on free agents that they really wanted.

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Teixeira and Lester. That's it. Yeah. So anyway. All right. Well, keep up dominating the podcast world. When are you going to winter meetings? Listen, we go Sunday. Yes. Well, Sunday because I got to coach high school basketball on Wednesday. That's a good thing. That's more important. Hey, listen. Are you playing man-to-man? Tell me you're not playing zone. I do it all. We'll talk off.

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All right. All right.

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