Winter Meetings Day 2 Recap: Schwarber Rejects Pirates, Internal Shakeups & Draft Lottery Drop

Yo yo yo, welcome to the Northshore 9 podcast presented by FanDuel. I’m your host Anthony Dinardo. With me, of course, we have Jim Rosati. We’re both here live at the Winter Meetings in Orlando wrapping up day two. Day two is over and uh not a not a great day for the Pirates. Not if you’re a Pirates fan. No. But I feel like overall again once again it was like a pretty slow day for the winter meetings in general. Uh last year was pretty popping. You know, it been kind of slow most years. Last year was a pretty eventful year. This year seems like it’s going to be one of those slow winter meetings where I think most teams most fan bases are maybe hoping that the talks progress and then they happen afterwards. But if you’re a Pirates fan especially, it was uh it was a sad day. Yeah, there’s still some time. I mean, at this time last year, not a whole lot had happened. Uh and then, you know, the Horwitz trade dropped. Yeah. Uh pretty late on on Tuesday night. So, you never know what could happen after we record this. Who knows? We might be doing an emergency podcast at like midnight tonight. I hope not. Or actually, you know what? I hope we are. I hope we do. For your sake, I hope we do, too. But but maybe don’t watch it. But no, it’s been You had the Schwarber. Schwarber officially signed a contract today. He’s going back to the Phillies. Five years, $150 million. Really, the the interesting here interesting thing here is, you know, the the Pirates did make an actual official offer. 4 years, $125 million, which means they actually offered Kyle Schwarber more annually than the Phillies did. But the Phillies with the fifth year got it done. I know we talked about this last night where we were like, I don’t think four years is going to do it. I think it’s going to have to take five. And it sounds like what happened is, you know, Schwarber, their camp officially got that offer and then kind of was like, hey, anybody else you want to beat this? And uh the Phillies did. Uh and now he is a Philly, right? And it was reported to like the Orioles matched that offer and he decided to go back to the Phillies as well. We already know that the Pirates again had the four-year 120 was reported last night. 125. Alex reported from sources that it was, you know, 125. Again, not much of a difference. It was four years instead of five years, but it was kind of interesting that the Pirates based on that source gave more money per year. Um, and then the Reds were also in their five-year deal. Sounds like there was, you know, much less money in total as well. But yeah, I mean there’s certainly a market for Schwarber. He probably, you know, the agents might probably use the Pirates in the sense like that’s why that information being fed. They want, you know, he probably said to his agent, I want to go back to Philly, make that happen. The Pirates did have a legitimate offer though, like I want to stress that it was a legitimate offer. That was something that you could probably entertain. Uh, not really what Sha wanted. He got his way to get back to Philly and the money that he wanted. So, worked out that way for him, I’m sure. But again, I think the most interesting thing about this in the Pirates terms, I mean, yes, you have to get it done if you want to prove they didn’t get it done. So that is what it is, but they were willing to spend $125 million on a player in the year 2025. Now, I understand that’s not something that’s completely amazing, but the record right now for a free agent uh contract is $39 million. Yeah, you kind of look at this twofold. one, it it is like as far as I know, I’ve never I can’t recall a free agent that the Pirates went after, you know, that was this marquee of a guy, right? Uh and like actually tried and like made an official offer that was I mean, let’s face it, it’s a competitive offer. Like if you go on fan graphs and and you know the free agent tracker, uh the Pirates offered Kyle Schwarber just about what everyone was thinking he was going to get. So it was the fifth year that ultimately got it done at the same at a slightly lower AAV. Now with that being said, like yeah, do you I don’t I still don’t think you can give them any credit. Like this this Hey, the Pirates tried. Yay. Well, like they should always try and you don’t actually like you get nothing for coming in second place or third place or fourth place, wherever it was that they ended up. You don’t get any credit for that. That doesn’t translate to wins and losses in 2026. So eventually, you know, all these guys that they’re in on, they they have to actually acquire somebody before any one of us and any fan is going to actually really believe them when they hear things like, “Yeah, this is going to be different.” Like, so far it’s different in that they they are telling people they’re trying cuz like that typically isn’t what what’s happening, but it hasn’t been any different in terms of actual results. So, we’re still in wait and see mode. Yeah. Uh, for sure. For sure. And I I want to make sure I stress, you know, that point, too. Like, none of us are happy about that. None of us are saying here like, “Oh my god, like look what the Pirates did.” But it is interesting. I mean, they had a contract out there for $125 million. So, again, like what’s now that it’s over with, right? Now, that short isn’t there. Now, how do they pivot? Like, to me, that’s what’s important. You’ve shown face now. You’ve shown that like, hey, we’re ready to pony up $125 million. Well, then you’re ready to pony up $125 million. So then like again it can’t be like we’ve been talking maybe assuming like okay it’s a Palanco and O’Harn, you know those type of free agents. It still could be but like now you’ve entertained the possibility of $125 million contract. Okay. Is it Bellinger in playing? You know it are one of the Japanese guys like are there possibilities of better tiered players? I don’t know. But you’ve shown face that like you entertained it. So again, I think to me it’s like I I understand Schwarber didn’t happen. That’s one player. So what is next? Something does have to happen. And you really need to make sure something happens because again, you showed face here, but $125 million contract being floated out there. Yeah. You can’t tell people that this year’s going to be different. You can’t tell people this off seasonason is going to be different and then not have it be different, right? You know, like that just makes you look even worse than you already do. I mean, the Pirates have been a laughingstock for years now. If they go out here and they’re telling everybody that this year is going to be different, it’s going to be different, it’s going to be different, and it’s not, then all you did was just smear egg all over your face. Exactly. You know the fan base right now. You know how riled up they are. You know how they just don’t trust you and and just believe anything that you say. So like when you put out the four-year 125, I’m not saying this is why or whatever, but like you hear a lot of people like, well, yeah, that’s you knew Schwarber was going to take that because Schwarb wanted 5-year. So you can give something and have people say it’s really competitive, knowing you weren’t going to get it, but it’s out there. So like, you can’t put out this contract and then roll into March saying, “Well, here’s a one-year $10 million value player. You know, hey, we tried on that guy, but it didn’t work out.” Like no, now you really need to make an impact. like this off seasonason has to be quite impactful and again that 125 can backfire on you if you’re not making an impactful offseason. Yeah. And Ben Sherington uh spoke to the media a little bit today and and he did mention that, you know, the goal like he he he’s he says there’s like groundwork is being laid. There may not be something that happens, you know, later today. There may not be something that happens tomorrow. There may not be something that happens next week. But he he even he did say, you know, he anticipates something probably happening by like Christmas. Uh he, you know, he mentioned that. Uh and he did mention that, you know, it’s that they’re probably going to be working all off season to improve this team. So, it sounds like they’re not going to just go out there and just do everything right here at the beginning. It’s going to be a long process. Uh and I said hopefully hopefully something gets done uh that that improves the 2026 Pirates, but at this point, we’re still waiting. stressing it one more time. Nothing truly matters until it happens. But I do want to state kind of pivoting, not really pivoting, but carrying over what we said last night. The vibes were different from people we talked to this off season. The message is different. You know, we’ve we’ve more or less entered every winter meetings beforehand of, you know, what’s this team going to do? And it’s like, well, we anticipate we want to get better. We want to get better. We’re going to try this. We’re going to try that. I feel like the messaging has been quite different. Now again, it doesn’t matter. They could just be pivoting and saying, “Well, hey guys, these adjectives and adverbs don’t work because we’ve we’ve exhausted them. So this offseason we have to use these new types of adverbs and adjectives.” It could be it that could be that. But what I’m telling you is they’ve changed their way of messaging and it’s gone from like we need to try to get better and we will. We have to. It’s going to happen. do we just have to fill things out and let things come to us? You know, like like I’ve been using that term, right? They’re gonna cast a large net. And they Ben uses it today on the MLB network, but like that’s essentially what he’s talking about. There’s a large net out there. We are going after hitters. Schworber fell. It didn’t happen. That’s just one chip. Now we have to pivot to the next one. We need to, you know, you’re going to cast a net trying to get a 100 guys. You need three or five of them. So again, what is most important at this point in time that you’ve failed in getting Kyle Schwarber is landing that next one. Yep. Yep. And I said some that was just the first bad news item today. Second bad news item uh dire director of pitching development Jeremy Bleach who uh who who’s been overseeing the pitching development program uh over over the last you know handful of years. He uh he is poached by the Arizona Diamondbacks. he now moves into an assistant general manager role there. So, you know, you look at something that the Pirates have done pretty pretty well, pretty pretty well at, uh, which is developing pitchers and and getting them to the majors and making them contributors. The the guy who’s been in charge of that program, no longer with the Pirates, uh, like I said, being being poached out. So yeah, definitely some discouraging news there that like said we and we’ve talked about this before where the Pirates have um you know there there don’t seem to be a lot of people who have executed very well uh over the over the past handful of years. um the the ones who have Justin Horowitz and now Jeremy Bleach uh both poached by other organizations for higher roles where it’s like hey it would have been really cool to maybe keep those guys uh did we do everything we could to maybe elevate their their uh elevate those guys in the Pirates organization? I don’t know. Uh but yeah, that was that was some rough news today as well. Yeah, it really was. Um but it is what it is. I mean, you hear people talk about that, you know, hey, it’s a sign of a good organization, right? You’re going to you have good coaches, you have good people in your system, they’re going to get poached, you’re going to move on, right? I I just tend to believe that that’s not really the situation. It’s that hey, there’s a few like really good standouts and they were poached. So, because again, let’s be honest, like this is a team that had 76 wins, 76 wins, 72 wins, year six, right? So, I mean, things haven’t been going well. Now maybe things get better on some fronts and they’ve they’ve infused this organization with some talent but again like Justin Horwitz was one of them like he was a new guy that came in you saw the drafts improves like hey they are infusing it with talent and then he moves on rather quickly and like you said that’s kind of like what I think the bummer is they see the talent why didn’t they do everything they could to maybe keep it like why couldn’t they promote them to another role um so yeah another thing where like there was a really good bright spot on this uh team organization system and now that’s gone. So yeah, and who knows? I mean, maybe that maybe they tried. Yeah, you know, maybe they tried. True, true. And again, doesn’t mean that it’s gone. Doesn’t mean like, hey, now the system’s broken. They won’t develop pitching anymore, but that was a bright spot and yeah, they moved on today. So again, yep, a list of bad news that happened today. Uh, and then we move on to the MLB draft where the Pirates had a third best odds. Uh, you know, of course, maybe they can get the number one pick. is a really really good member that’s going to get drafted next year that could go number one overall. Of course, there’s still a whole season to go. We saw what happened to Kumar Rocker, right? It was Rocker or bust and then well, Rocker kind of busted, right? And it worked out for the Pirates in a sense. But, you know, again, like right now at this point in time, see if they get their one pick. They had a third best odds and they end up at number five. Yeah, the draft is a really it’s it’s far away. JJ Cooper, we talked to him earlier this morning and you know he he stressed that like there’s a clear-cut number one guy. Uh but like a lot of things can change. I mean there still needs to be an entire college season played an entire high school season played a bunch of showcases out there. So there’s a lot of baseball to be played. Who knows what it’s going to what’s going to happen there. The Pirates get the fifth overall pick which is like you know worse than what you would have hoped for based off of their odds. But they got a pretty good pick at number five last year. They got a really good pick the year before at number nine. So, it’s not like there’s going to be no talent available to them. It’s just now they got to they got to identify the guy who’s going to be available there and uh yeah, make it a good pick, right? But it’s kind of interesting again like the the lottery how it is it again it’s just interesting. It’s not based off your record. You know, you get odds. It’s a lottery. So, you could have a team like the Giants who didn’t have great odds but they end up with the number four pick I believe. So they jumped I mean they jumped I think 10 or more spots and you have teams that kind of fall where they were like the Marlins to some degree. So again like that’s cool about the draft is nothing’s guaranteed. So you can have the biggest loser of losers and they don’t get the top pick and you can have a guy who tries and they end up with the top pick like the Guardians a few years ago. Yep. Uh so the Pirates get the fifth best uh pick next year. But the interesting about that is now they had two lottery picks in a row. So what’s going forward is for next year uh they won’t be able to to pick in the lottery. So, kind of like how the Washington Nationals ended up with this year. Yep. So, the next year the uh the highest they will be able to pick is 10th, right? So, when you know you can’t get a top 10 pick or I guess top nine pick, uh just go for it, right? Yeah. Just win some games. Just win some ball games. Let’s just do that. Yeah. So, there’s some more incentives to do what you need to do this offseason. Ben Sharington. Yep. Uh but outside of that, you know, it was it was it was a day. It was an eventful day for us. We have tons of content out there. talked to quite a few people. I mean, obviously manager Don Kelly we talked to uh some interesting stuff that he talked about. Also gave us his Permanis sandwich. Yeah, big roast beef sandwich guy. Not a capp and cheese. So, I mean, I don’t know. Kind of a strike. We’ll see what happens, dog. Yeah, we’ll see. Um, but no, yeah, today it was a good day. Like I said, lots of stuff out there for you. Again, JJ Cooper from Baseball America we talked to this morning. He answered your questions on the Pirates system. Make sure you check that out if you haven’t already. Uh after JJ, we talked to Jolly Olive from Johnboy Media. That was a fun conversation with him. Just a honestly genuinely great dude. He really is like like I mean you know you see him on on YouTube on on social media and stuff and but like seeing him in person like it this it’s nice when you see like oh this is genuine. Yeah. So awesome guy. Listen to that. Also again like what’s cool about him is like for some reason he’s like in tune with with the Pirates. Yeah. It’s like his number two team. Freddy Sanchez, like his favorite player. So, big Freddy Sanchez guy. Yeah. So, listen to that. And then, of course, wrapped it up with an AMA with uh Jason Mackey, who had some, you know, pretty good insight. A lot of questions. So, we thank you all for joining. So, those are our three AMAs. The Don Kelly interview, of course, I wrap up today and maybe maybe Jim, an emergency podcast at midnight. I don’t know. Let’s let’s see. Let’s let’s see. But tomorrow, rule five draft. Uh so, there is that. Of course, we’re going to have a little more AMAs. probably Stephen Nesbbit, one of them wrapping up maybe some more guests. But uh again, hit those alerts. Hit that subscribe button. Follow us. We got some more content coming your way. And then Sick Sound off on Friday. I’ll be hosting that. That’s your way of tuning tuning in, chiming in, just going wild crazy. Of course, the theme will be the winter meetings. And uh hopefully we’re not too disappointed, but if we are, well, you have a place to vent. And also NS9 Live tomorrow. Uh we’re going to do it an hour early so we can get out here a little bit earlier, but 800 PM we’ll be doing NSI live here from winter meeting. So yeah, looking forward to that, too. Hopefully we got a hopefully there’s an eventful day to talk about. Yeah, hopefully. So with that said though, we are out of here. Uh we’ll see you guys tomorrow bright and early once again unless there’s an emergency podcast. But until next time, byebye. See you guys.

Live from the MLB Winter Meetings in Orlando, Anthony DiNardo and Jim Rosati recap a rough Day 2 for the Pittsburgh Pirates. Kyle Schwarber chose the Phillies despite the Pirates’ legitimate 4-year, $125M offer, leaving fans wondering what the next big move will be. We also break down the loss of pitching development director Jeremy Bleich, the Pirates falling to No. 5 in the MLB Draft Lottery, and what all of this means for 2026.

Plus reactions to our Day 2 conversations with Don Kelly, JJ Cooper, Jolly Olive, and Jason Mackey, and what’s coming next with the Rule 5 Draft and NS9LIVE!

Subscribe for full Winter Meetings coverage all week.

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