MLB winter meetings Day 1 recap: Will Pirates’ Ben Cherington make a big move? What’s real and fake?

MLB winter meetings Day 1 recap: Will Pirates’ Ben Cherington make a big move? What’s real and fake?

What’s going on everybody? Greetings from Orlando, Florida. We are at the uh MLB Winter Meetings. The place that we’re at, it’s called the Signia by Hilton Orlando Bonnet Creek. That’s a mouthful. Uh but anyway, it’s the site of the MLB Winters winter meetings, an annual event here. It’s a lot of fun. I’m Jason Mackey. Colin Beasley is on the other side of your screen if you’re watching on YouTube. And thank you so much for finding us. It has been a busy day. Uh both of us are probably loopy at this point. We’ve listened to Ben Sharington and Don Kelly talk. Uh we’ve been writing, we’ve been transcribing, we’ve been talking to various people around Major League Baseball. It’s been a lot of fun. It’s a fun busy. It’s a tired busy. All that fun stuff. You see people in the background. This is just normal protocol for here. It’s kind of tough to find a quiet spot. Colin found a little bit quieter quieter of a spot than I did, but uh we decided to do it this way rather than cuddle up close. But anyway, a lot to break down for you. Again, Don Kelly talked, Ben Sherington talked. Uh we’re going to talk about the Pirates sense of urgency. Uh what Ben Sherington said about adding more pitching, whether Connor Griffin might be their opening day shortstop, whether he’ll sign a contract extension, the future of Andrew McCutchen. Uh and also an area that the Pirates, maybe we didn’t expect, they could look to improve. We’ll see. There’s all kinds of stuff to run through. Uh first, we do have some odds from our friends at FanDuel. The Dodgers are plus 180 to win the National League. Obviously, a lot of Dodgers people in talk here. The Phillies are second at plus 500. The Pirates are plus 10,000. The Yankees are the favorite in the American League at plus 330, followed by the Mariners at plus 550. For more, you can visit sportsbook.fanuel.com. All right, so let’s get into this. Colin, U. Let’s talk urgency first. I think that was sort of the overarching theme of the day. Don Kelly talked about what it would mean to him to win in Pittsburgh. Ben Sharington talked a lot about what they’re doing this off season, the Pirates being connected to uh all sorts of free agents, trades, uh interest all over the place. What did you make of this idea of urgency and the Pirates really supposedly having a different off season? I agree that that was my biggest takeaway, too. I was I was struck by the urgency from Ben Sherington. I was struck by the urgency from Don Kelly. I feel like they really understand that this is an off season that they have to get right and this is a unique opportunity to be competitive. One of the things that also was eye-catching for me is how Ben Sherington kind of understands that in terms of offensive improvement, the bar is pretty low in terms of improving the team. There’s not it’s we focus a lot on how the Pirates need to improve left field and third base as their two biggest weaknesses. However, Ben Sherington seems to understand that or Ben Sherington said that um they’re not just limiting it to those two. They’re willing to look at pretty much anything. They’re willing to look at maybe it’s power, maybe it’s getting more speed, maybe it’s getting a left-handed bat, maybe it’s getting right-handed bats. He’s not ruling out anything because of how much this team struggled offensively in 2026. Yeah, I thought that was one of the better quotes from Ben’s availability. And I have it right here. I’m going to read it real quick. In sort of a perverse good way, our bar is such that we can improve in any number of areas. More on base, more power, more contact, you name it. We need all of it. I think we need some combination of both, just better depth. Uh, and he went on and on, but that’s the idea. And that’s what you’re saying, Colin. Like it it doesn’t matter. They need to add bats. It can be any number of ways. Um, it’s the deepest I think I’ve ever heard Cherington describe their needs. You know, it’s always like, “Oh, we’re always looking to get deeper. We’re always looking to add to our position player group.” Like, no. He basically said, “We were the worst offensive offense in the league and there’s a lot of places to add. We can’t afford to be too picky.” And frankly, I was glad to hear him say that to admit where they are and there’s a lot of room between where they’re at right now and where they need to be. Yeah. wasn’t him saying the bar is on the floor, but it’s also not that far away from it. Like he he wasn’t that blunt. He shouldn’t be that blunt, but there’s a lot of things that you can do in order to improve improve offensively. Yeah. And he also talked about having a confidence that they can execute and get something done. Um I found that interesting, too. He said it doesn’t he doesn’t know whether it’s going to be today, tomorrow, the next three days, next week, next month, whatever, but he’s confident that they’re going to get something done before spring training. I’m going to ask it to you this way, Colin. How much urgency do they need to have in terms of just like having this stuff out here? Like, would it benefit them to get something done during the winter meetings to show that they’re serious? I think it would. I think that you have some momentum right now after making the trade for Garcia, the Ovado for Garcia trade. I think that once that something they really struggled with last offseason is they made the one trade and then they didn’t do much after after acquiring Spencer Horwitz. I think that that was the biggest thing that went wrong. Um, is that Brian Wari in the background? I don’t know. That’s awesome. There could be anybody. If you’re watching this, make sure you keep your eyes peeled. Anybody could be watching walking behind me. But anyways, what I was saying is that um I got I I lost my train of thought there a little bit. Yes. Yes. I on one hand on one hand you have until spring training. It doesn’t really matter whether you sign a guy today or whether you sign a guy in a month. But right now you have all sorts of options. You can trade for just about anyone. You can acquire just about anyone. You can sign just about anyone. Not many free agents are off the market. not many trade pieces have gone anywhere. Whereas in a month, you don’t have as many options. So on one hand, it doesn’t matter like whether you have your team assembled today or whether you have your team assembled March 26 on opening day, but the more you have more options by making a move sooner. Yeah, you absolutely do. And one move they could make, Colin, and I don’t think this is terribly likely given the Johan Ovo trade, um, but they could deal a starting pitcher. I was a little surprised to hear Ben Sherington say that uh or maybe the way he said it uh because he did go into some details and I know this is something that you wrote about at postyphengazette.com uh that the Pirates aren’t against trading another starting pitch pitcher, but there would be some sort of ripple effects in pitching. As much as we’re talking about hitters and having to improve the lineup and all that stuff is valid, there was some conversation about pitching too. As both Don and uh as both Donnie and Ben mentioned when talking about the Garcia trade, you have to give up something to get something in a trade. The Pirates still have starting pitching. They still have depth there. Yes, that depth is tested. Right now, you’re rely you’re relying a lot. I think a free agent signing is possible regardless of what they do. But the Pirates have depth. That still is their greatest strength. That is the best thing that they can offer any of these teams in a trade. With me, I really more read it as the Pirates don’t want to rule anything out. They want to be in the market for just about anything. Ben even mentioned that. He said that he’s um that they’re in they let me see if I can pull up the exact quote. You chase a 100 things in three, four, five land. That’s still the stage we’re at. That’s kind of what I see there. That’s in free agency. That’s in trades. that’s in just about everywhere on the market by putting themselves in every single giving themselves every single opportunity. If you land three, four, five, you’re in a pretty good spot. Yeah. And I there’s a I guess a second part of that, too. Like if they would trade a starting pitcher, like maybe it’s Mitch Keller, maybe it’s Braxton Ashcraft, I don’t know. I’m just picking a random name. But, you know, if that deal, if they need to make that deal to improve the offense, they’re also not afraid to go out and sign somebody via free agency in backfill. I guess that was something that I wasn’t considering as much until hearing Ben Cherrington say it today. Uh, something else he said uh and was he was pretty open about this was the bullpen about looking to add in the bullpen a couple pieces. How likely do you think that is? I thinkly I mean at a bare minimum you need one or two lefties in there. You’ve got you had two you had three lefties on the 40man roster. You they uh dealt San Diego in the Ovido trade. So you need you need another lefty in there at a bare minimum. I also wouldn’t be shocked if they went after a high leverage guy. Someone that they could pair with the Dennis Santana and Isaac Matson’s of the world and really beef up the back end of the bullpen. I think that that’s something important even though they do have a lot of guys who can contribute. What did you think about talking about, you know, we were talking about the Odo trade, uh, and Joe Stinson, I think I nailed it, Garcia, uh, getting him back. They both spoke on this, and I I thought it was interesting, too. Cherington talked about he’s part, it was almost like a baseball trade wrapped inside of the larger scope of their off season. And I think they really like Joe Stinson Garcia, but my takeaway from it was this guy’s not immediately going to be in their outfield. I think he’s probably ticketed for Triple A unless he has an absolute bonkers uh spring training or there’s an injury. I don’t think they want to rush him. I think they really liked him, but you know, I guess before I arrived here, I thought maybe he might be a bigger part of things in 2026, but I don’t think they’re, you know, they’re not looking at that as a solution for 2026, where I think fans might be looking at them externally and saying, “Oh, you did this because it’s some sort of cheap fix for this upcoming season.” and that’s not the way they’re looking at this thing. I think they still expect him to contribute and have a key role in 2026, but it’s fair that they don’t want to declare him the opening day starter. They want to Hey, you got to see what else you can get. It’s entirely possible they sign a legitimate bat in left field and then okay, he’s not starting then why would you say he’s the starter if you’re going to go out and sign someone. Other thing is if he struggles in spring training, you should be able to have the option of putting him into AAA. He’s someone that’s had believe it’s seven major league at bats, it’s it’s right that they’re not declaring him the opening day starter, but I’ I’d still expect him to be a relatively important part of the mix there. Still not the not the number one option or not the only solution though. They need to do more and I think they realize that. Yeah, absolutely. And I think they will do more. And I mean, some of the stuff you and I were in, some of the same conversations earlier, hearing from agents and people around the industry about the Pirates plans and and what they’re showing as far as their intentions. I mean, I feel pretty confident that it’s legitimate. I mean, I I don’t know what’s going to land for them. I don’t think anybody does, but they’re very aggressive. You know, they’re either faking it in an absolutely gigantic way or I think they’re going to actually do something here. I want to talk on the second half of this Colin about some players specifically these guys were asked about O’Neal Cruz, Connor Griffin, Andrew McCutchen, what the future may hold for some of those guys. We’ll get into that and more, but first a message from our friends with Greenwalt Roofing. Hey Pittsburgh, when you think of great roofs, you think Greenwalt Roofing Company. 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Um and about his place on the roster and does there is there a fit for him? Is there a spot for him? How the Pirates are going to go about doing this? Uh what was your takeaway from Ben’s answer on that, Colin? I’d say it was very very non-committal. Another option, another point where they’re keeping all of their options open. It wasn’t a no, Cutch is not coming back. It wasn’t a we will sign him immediately. It was we’ll see. Ben kind of said that we that they have to see what happens with the roster. They’ve got a lot of moves to make. They’ve got a lot of internal external moves to make before they get to that point. I think it’s something where I it didn’t really change my opinion. I could still see them going either way on it and Ben Sherington seems to think the same. Yeah. You know, one of the things that I thought hearing him talk about it, and I didn’t expect him to sit in the media availability and tell us, hey, yeah, Andrew McCutchen’s coming back, by the way, I meant to tell you, you know, like obviously that’s not going to happen. But what he basically did tell us was that they have a whole bunch of stuff to figure out before they can talk about Andrew McCutchen in his role. And if we look at the Pirates and everything they’re trying to do, and I’m talking about offering Kyle Schwarber, um you know, Catel Marte, Jorge Palanco, at all, you know, like name a free agent. They basically either or trade possibility like they’ve basically expressed interest in them. What if they land them? Like, if you end up having a full roster and you can’t promise Cutch any sort of meaningful playing time, I’m not sure Andrew McCutchen’s going to even want that. So, like I take his answer and the Pirates actions. I just I have a tough time seeing there’s going to be a spot for Andrew McCutchen on this roster based on the way they’re shopping. Now, another part of what Ben said that I thought was important and he talked about respecting him, respecting Kutch’s career, Pirates contribution, the contribution to baseball, whatever. Um, I don’t think that was by accident. So, I do think there’s an acknowledgement by the Pirates that they have to do right by Cut or that they should do right by Cutch, but it is a very tricky ven diagram for all of that stuff to uh to really work out. All right, let’s move on to Connor Griffin. um somebody at a different point of his career. Um Ben was asked two different questions about Conor Griffin. One was whether Connor Griffin could potentially be their opening day shortstop in 2026. Also, will they get together and have a discussion over a contract extension with Ben Cherington? Ben did not say a whole lot. Basically said they’re not at that point in the offseason to talk about whether Griffin will be up and you know the contract extension that’s down the road too. What do you think based on at least hearing the tone, seeing the body language, his answers, uh some other people we’ve talked about, do you think there’s a real chance there’s a Conor Griffin contract extension and a real chance he’s there on opening day? Only the thing I’m confident in is that there will be conversations. Ben kind of said that it’s not like now isn’t the right time. This is something that they’ll get to a little bit later in the offseason, but he did it did seem like there’s interest there. I’ I’d expect that to be something that the Pirates broach a little bit later later in the offseason. As for whether he starts the season in Pittsburgh, I think it’s I both him and Don Kelly kind of mentioned that they haven’t thought about it too much yet. Again, early in the offseason, you don’t know whether the Pirates are going to go and sign a shortstop or exactly what will make sense there. Um, but I do think there’s an opportunity for him. I do think there’s a chance, but I also think it’s beneficial that they’re not saying, “Yes, he’s 100% our opening day shortstop at this point.” Yeah, I agree with that. I do think though to build on it, I don’t know if there’s a better investment they can make right now than signing Connor Griffin to an extension. Like, you’re talking about throwing around a lot of money. Like, if they’re if they’re comfortable paying Kyle Schwarber $30 million a year, like that’s great. I mean, I I’m far be it from me to to talk them out of spending money, but I’d almost rather have them extend Connor Griffin and then go get somebody for $20 million or something like that and, you know, assure that he stays there. Uh, and I do think he should be on their opening day roster at shortstop. I mean, unless they do something else right now, he is their best available option even without a contract extension. Like, that guy can help your team. I’d like to see him up here. I like like we were saying, we’ll get later in the off seasonason and see how real any of that is, but uh a lot of excitement over Connor Griffin. Last player I want to talk about, Colin, is O’Neal Cruz. Um I asked Donnie Kelly about how do you bring more out of O’Neal Cruz? To me, you know, outside of the external additions, if you talk about internal improvements, O’Neal Cruz is circled and highlighted and all these other things. Uh but what’s their plan for getting more out of O’Neal Cruz and and what would you like to see change in his game in 2026? Sounds like they’re working really closely with him throughout this off seasonason. They mentioned that he’s done some work at their facility in the Dominican that he’s done some work with the Pirate State side. Matt Hagen, the others in the hitting group are working closely with O’Neal Cruz throughout the offseason. I that it’s it’s clear that that’s the most obvious place for internal improvement. That’s something where you could legitimately see a player go from a near zero war player to someone who could be up in the 3, four, five range. And that would help the Pirates so so much. That’s their biggest that’s that’s the biggest switch that you can flip in order for this team to improve is simply helping O’Neal Cruz act on some of his potential. What I’d like to see from him more in 2026, I I I don’t I think it’s all stuff we’ve talked about before. I want to see some more aggressiveness from him. I want to see him cut down on swing and miss. I want to see the strikeouts dip a little bit. I want to see that average go up. And I’d like to see him get back to being the game-wrecking O’Neal Cruz that he’s shown in flashes he can be. I think that that’s something that the Pirates can certainly work with him on. I don’t think it’s out of the equation and it’s clear that the Pirates realize how important he is, too. Yeah, no doubt. They need more consistent contact from him. I don’t know what happened in the middle of the season. And I don’t know if he was worn down from not playing that much center field or what, if if his legs gave out or um whether it was just swing decisions or whatever, but I mean, yeah, I I can cosign that with you. There is no bigger internal improvement. Just have to get through to O’Neal Cruz. All right, let’s let let’s end on a fun one here. Um this has been a wild day. I know I woke up in Dallas very early. I feel like, you know, kind of blur eyed or something. It’s just weird. This is your first winter meetings. They’re fun. Um, what’s the experience been like for you so far? It’s awesome to see so many people out and about where you just know that they love baseball as much as we do. Like we’re talking to scouts, we’re talking we’re talking to scouts, agents, managers. There’s been a play or two hanging around. We’re talking to all sorts of baseball people. And it’s it’s kind of like our our people. Like these are guys who love baseball as much as we do. and getting to have conversations about the greatest sport on earth for an entire day and writing about it and hearing executives talk about it like it it’s just it’s just really cool to be in this sort of environment. What about you? I love it, man. We were walking to uh Ben Sharington’s media availability and I saw a scout that I talk to all the time and I didn’t know he was going to be here and he didn’t know I was going to be here and I like pushed him and then he’s like, “Hey, what’s up?” Gives me a hug and um we’re talking about like covering the Penguins briefly. It’s just like that’s what happens. You bump into people randomly and you like set up meetings with people that you know and say, “Hey, I want to introduce myself.” And um you you and I got to talk to a couple people together. And it’s just it’s stuff that you can’t experience when you’re not all under the same roof. Um and it’s also like crazy confusing. This isn’t a complaint. I’m saying that I’m like hesitating because you know people don’t want to hear it but um like you see the the walkway behind me and there’s just like miles of walkways almost like between hotels like regardless of which way you go you can just get like lost and there’s people everywhere you go and it’s almost like New York City in a way you know like we’ve been here all day and this will go on for a long time and we’ll just walk around like we do need to go get a bite to eat so uh I think both of us are kind of feeling that one But, uh, there’s just people, activity everywhere, like you’re saying, all kinds of, uh, like-minded individuals. But, yeah, I, this is not my first rodeo covering one of these things. But, I do love it. It’s fun. It’s such a weird kind of tired. Both of us aren’t going to have trouble sleeping tonight, I wouldn’t imagine. Um, we’ll be back at it bright and early tomorrow. Uh, speaking of which, very busy day. Don Kelly won’t talk tomorrow, but Ben Cherington will. Uh, we have a BBWA meeting in the morning and a whole bunch more to break down for you. So, uh, I don’t know. Good talk. Anything else? Anything else to add? Let’s get some food. All right, let’s go get some food. Thank you guys so much for watching. Make sure you like and subscribe. You can get all of this content, so much more from our Post Gazette Northshore Drive podcast and YouTube channels for Colin Beasley. I’m Jason Mackey and we will talk to you tomorrow. [Music] Thank you for checking out this content from Postgazette Sports. If you watch this video on YouTube, please like the video and subscribe to our channel. For all the sports coverage that Postgazette has to offer, visit post-gazette.com. [Music]

Post-Gazette Pirates insiders Jason Mackey and Colin Beazley recap Day 1 of the MLB winter meetings in Orlando, Fla. This show is presented by FanDuel.

Which rumors related to the team are real? And which are fake? Particularly with regard to reports tying them to free agent power hitter Kyle Schwarber? Could GM Ben Cherington and manager Don Kelly make a big move involving their pitching depth, which includes names like Paul Skenes, Mitch Keller, Jared Jones, Braxton Ashcraft, Mike Burrows and Bubba Chandler? What’s the future with the organization for big names past, present and future including Andrew McCutchen, Konnor Griffin and Oneil Cruz? And what did the front office have to say about the trade involving Johan Oviedo and Jhostynxon Garcia? Our duo tackles those questions and more.

For more Pirates coverage, visit: https://www.post-gazette.com/sports/pirates

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