Yankees checkup: Quiet offseason, Potential Skubal trade, Judge’s prime clock ticking, Hal’s profits

Foul Territory

The Yankees have had a quiet offseason so far. Pinstripe Territory host Derek Levandowski stops by with thoughts on Brian Cashman's plan, a potential Tarik Skubal trade, Aaron Judge's prime years clock ticking and Hal Steinbrenner's profit comment controversy.

For more of Derek Levandowski and Yankees insight check out Pinstripe Territory, part of the FT Network!

Hosts: Todd Frazier, Erik Kratz, Scott Braun

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2025-12-13 23 min Transcript

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Transcript

00:00:02
Speaker 1: Here he is. We're back at it. Derek Lewandowski, star of Pinstripe Territory. You can check them out all off season long, and then of course during the season after every single Yankees game. Well, Derek, I know you jump on as quickly as possible when the Yankees make a move. So how's life not having to scramble to the studio?

00:00:20
Speaker 2: So far?

00:00:22
Speaker 3: It's been kind of a low key winter. I mean, I'd much rather have an active off season. But there's sort of a little bit of fun in the tension too. It's kind of that, you know, will they won't they in a lot of different areas, and it's one of those off seasons where the path isn't real clear. You know, when they wanted to get Jan Soto, right, that was all anybody was talking about. Well, they go out and get Sodo.

00:00:44
Speaker 2: He's the perfect fit.

00:00:45
Speaker 3: You know. Last year it was a lot of will they get you know, Cody Bellinger? The the plan usually is a lot more clear than it is this off season. But the fact that Trent Grisham has come back and except that qualifying offer, it complicates things, right because now if you sign Bellinger or if you sign Tucker not only are you two left handed, but you put a big boulder right in front of both Jason Dominguez and Spencer Jones, one of their top prospects. I believe Brian Cashman when he says he's searching for pitching and a right handed bat. A lot of times fans don't think that Cashman is very forthcoming, But if you listen to him and the tea leaves he drops a lot of times he will tell you exactly what the Yankees are looking for. And I think he wants to get more right handed and I think he knows that the only way you win in baseball is by having good starting pitching. Yankees are a little bit hamstrung in terms of their pitching to open the season. I could see him trying to reinforce the rotation, maybe get a bullpen arm or two, and maybe a couple of unexciting right handed bats that will actually make the Yankees more complete roster than they are right now.

00:01:53
Speaker 2: All right, I guess we're done then, D Like, you already went through everything and the Yankees haven't done anything. So what else can we talk about today? Now? I want to talk about that first. I want to talk about the right handed options, because I think that's the most boring discussion for the Yankees unless it's not unless it's did they just miss on the pee Alonso? Had it happened later on, would that have been the fit last year's right handed options that they acquired Paul Goldschmidt, Jose Cabairo like is is the right handed market too thin for the Yankees to go and get anybody that's legitimately gonna fit? And people will be like, what about Alex Bregman? You know, hal Steinbrenner doesn't go after a Bregman and and a Tucker and a Bell And you're like, Cashman is at the position where he's at. He's missed one playoffs in his entire career as at GM because he doesn't necessarily listen to all the rigamarow around you Yankees fans. So where's that right handed option? If if the tea leave that he dropped is true, they need to get a little bit more right handed.

00:03:02
Speaker 3: Well, he's missed more than one playoff in his career, so correct you There just a slight corrections to the record there. But I think there's a couple of names that are kind of floating under the radar that people might want to think about. First of all, a Miguel and Duhar reunion could be interesting. I mean, he mashed against lefties last year. You've got a left fielder right now in Dominguez who cannot hit left handed pitching just can't do it. We'll see how it works out. He's playing winter ball, but you know, maybe a platoon situation there. I could see him bringing back Amed Rosario. I was thinking about Josh Young from the Rangers. You know, he could be a platoon option at third base with Ryan McMahon. Not a lot of like big name, twenty million dollar guys. But if you read the tea leaves, it kind of sounds like they want to follow the Blue Jays model, which is, you know, not necessarily outspend everybody, but fill in the roster with you know, practical ballplayers to supplement your stars. And I could see them just bringing in kind of these role player guys, platoon type guys, maybe getting a few pieces that don't necessarily push the payroll too high, and then spending the big dollars on pitching where I know he will spend it. You know, if you look at the major contracts, he's given out in the last few years. You know, it's it's Carlos Rodon, Max Freed, you know, Garrett Cole twice. It's it's it's pitching that he wants to spend on. So I think that he will try and supplement with role player types in terms of the right handed bats.

00:04:30
Speaker 2: So right handed bats boring. I need bigger names. Tattis, give me tattoos. Tattoos. There's there's your big name. He just they just came Peler just came out and said he's untouchable. So that's not gonna happen to Miguel Andrew. Horror. You already ran him out of this city. He's not coming back. There's no way. Well he didn't.

00:04:50
Speaker 3: He didn't seem happy about his lack of playing time towards the end of his Yankees tenure. But I always liked him as a player. I know he's a fan favorite. I call him Migey two bags because he hits a lot of doubles. I just love those guys who just rake doubles, keeps action on the bases, He's always smiling, like I always felt like he was a good guy for the clubhouse, and obviously I'm not in the clubhouse, I can't tell, but he seemed like a good chemistry guy. In fact, does Yankees need more damage against lefties? And he is somebody that hits lefties, And I think that for the right price and an opportunity to, you know, get to bats on a winning team, he would consider coming back.

00:05:27
Speaker 4: Blue Jays took care of business last year. As we know, you see the roster construction of what they're doing and what the Yankees are doing. How is the Yankees gonna get to be those dogs again on top of the Al East because this Blue Jay team doesn't seem like they're stopping.

00:05:43
Speaker 2: Blue Jays are good. Todd.

00:05:46
Speaker 3: There was a lot of Yankees fans that called in or watched my show right after the series and they were ticked at the Yankees, And I was like, you know what, the Blue Jays they just they just beat us, right, They just they just completely kicked our butt. And it wasn't one of those situations where the Yankees beat themselves like in the World Series last year. I still contend if the Yanks had played better, they had a chance to win that series. But I mean, the Jay's just dominated and it's clear they're not going away, like you said, Will they bring back Bobashett? You know, could the Yankees maybe swoop in and steal their best contact hitter. That's something I would love to see. I've been a big Bobashett fan. I No, defensively, he's not the greatest, but he would give you a leadoff hit or a contact guy, another right handed bat, another infielder. You know, It'll be interesting to see if Volpi is actually able to come back from this injury at full strength. I know that he missed well. He wasn't as strong last year as they had hoped, and they said after the season that the injury was worse than they had thought, which makes you wonder if, like the surgery to repair it will hold him back more than was anticipated. Right, So I think that, you know, if you're not able to get guarantee that Volpi's gonna solidify that shortstop spot and do damage, you gotta look at other options. And Boba Schet's sitting out there for the taking.

00:07:09
Speaker 4: I feel like that's gonna be a hard one though, at the end of the day, getting him to come there. They got Cabrera, they got cay Baliro again, not the sexiest and things that we want to hear, but they can play. My next question to you is, though, can you I mean do mingas Spencer Jones. These are two really good prospects, and Dominga has been up there for Can you see a trade for enter one of these guys? I mean, dare I say Trek Scuobel with a couple other prospects to get him over to the Yankees.

00:07:38
Speaker 3: I could see it. I mean I never say never with Brian Cashman because I remember one February day, Alex Rodriguez was having a press conference holding up the Yankees jersey with number thirteen on it, and I never thought I would see that, And so since that day, I don't rule out anything. But you know, Schooble's one of these guys who can push you over the top in terms of a rotation. I mean, in the lefties, you run out there, win healthy Max Freed, three Scooble, Carlos Rodon and then righty's Garrett Cole coming back. Hopefully he'll be at full strength by the end of the season. I'm anticipating that he'll be hitting mid season for him, right around the time the Yankees are getting into the Pennant race, you know, and then Cam Schlittler. I mean, I mean, you guys saw what Cam Schlittler did in the postseason. The sky is the limit for this guy. I think that's five horses that win you the division. But I still think you do need a right handed bat or two to go with it, and you need some bullpen help. But Schooble's definitely somebody who would get Yankees fans excited. The issue there is that you got to re sign him. You know. It's the same issue that you had with Juan Soto. You make a trade, you acquire an impact player, and then he becomes a free agent and you lose the guys that you traded for him, right, I mean, Michael King, we lost him for a year, right. There was some other pitching depth pieces that we could definitely have used and they're gone now. And we only had Soto for one year. So if you trade for school, but you're definitely putting yourself in a tough spot in terms of death.

00:09:10
Speaker 2: November twelfth today, I'm sorry, December twelfth only off, my only off by a month, But it's almost Christmas. Are the Yankees the third best team? In the American League East today where we sit with where the rest of the East has made their moves.

00:09:27
Speaker 3: I think so, and I think they were before the other moves were made. I mean, I'm counting on a healthy Red Sox team with Roman Anthony being better than the Yankees. I mean, they they would have beaten the Yankees, I think in that series if they had Roman Anthony. And you know, they've added Sonny Gray, who hates the Yankees and always seems to pitch well against the Yankees. So you know, the Blue Jays are going to be aggressive. We'll see if they bring back Bashett, but assuming they do, they're going to be strong again. I think Brian Cashman knows right now that this team has a chance to get to the playoffs, but they've got to really sort of steer the ship in a little bit better direction if they want to win the division next year. Right now, right now, they're a wild card team, you know, and you don't want to be in that position again. So there, like he said, there's still a lot of offseason left to make things happen, but we're gonna like to see a little bit more aggression here coming forward.

00:10:30
Speaker 2: Obviously, the Yankees will be the Yankees forever. But this is the Aaron Judge era. The Aaron Judge era has essentially five more seasons. Whether you think he's gonna age out, whatever, that's not the discussion right now. Is this really a big make or break off season for the sense that when you look at like Pete a Lonzo's contract is five years. When you start looking at like Dylan Ceez pitcher position player, his is seven years. This offseason, you're signing guys that are going to need to win. With Aaron Judge and the way you're talking right now, you want to make the playoffs, Like, yeah, you want to make the playoffs. And I don't think that's the that's the essence of having a Monument Park player on your team that you want to make the playoffs. No, you want to dominate and you want to create these next five years of dominance. And I think it comes down it shouldn't come down to a Cody Bellinger in this case.

00:11:28
Speaker 3: No, I agree with you one hundred percent. As Yankees fans, we want to win every year and we think that if you don't win the World Series, it feels like a failure because we've been trained to think that, but it's clear that with hal Steinbrenner and Brian Cashman in recent years, the plan seems to be get to the postseason, have a healthy pitching staff if you can, and try and win that way. Whether or not that's gonna work, I don't know. I agree with you one hundred percent. You got to maximize the Aaron Judge years. And whether it's five years, whether it's whether it's three years of his prime. I still think he's got at least a few good years left in him of I mean, even if he drops off ten fifteen percent a year, he's still elite for a few years. It's just how long is he going to stay healthy?

00:12:14
Speaker 2: Right?

00:12:14
Speaker 3: I Mean there's questions, There's always been questions about how that big body will age. I think in a couple of years, John Carlos Stanton is off the payroll, Judge can shift over to DH and kind of become that, you know, DH late into his thirties hopefully and continue to match. But yeah, we want to see him riding down, you know, afloat on the you know, canyon of Heroes, holding up the trophy. We want to see that. We need that, and right now, it feels like the Yanks are trying to give themselves a chance at that rather than let's go out and make it happen.

00:12:49
Speaker 4: Right.

00:12:49
Speaker 1: You don't look at them like he used to and say a best roster on paper, easy, right? You know they'll have to get upset. That's definitely not It's just, hey, they're in the mix. They're in the mix every year, they're in the playoff mix. I got two free you. But first off, who's the shortstop for the Yankees next year? I know you mentioned Volpi, but he's had two years that I don't think are championship level, and now he's coming off shoulder surgery. Cue the excuses when he's struggling, and that's not necessarily his fault. But guy's coming off shoulder surgery. Usually it doesn't look good. Matt McLean Actually there's an example. I don't know if they were different shoulder surgery. It just came to me just now. But he was a shell of himself this past season for the Reds. I don't think he has the leash to go through another season where he's not good enough.

00:13:31
Speaker 2: Yah.

00:13:31
Speaker 3: Yeah, So he was already getting replaced in games by cabal Row late in the season. So I think right now, if the season started tomorrow, cabbal Aro is your shortstop. Problem is we're one pulled hamstring away from having no shortstop. Right if caw By Arrow goes down, I mean, who's your backup? Oswaldo Cabrera's coming back from a broken ankle, Can he play shortstop? I don't know, I don't. I mean, and we got a cat in the background making a appearance. It's gonna be really awkward if he takes a dump right there.

00:13:59
Speaker 2: But I.

00:14:01
Speaker 3: Feel like, I feel like if when Volpi comes back, the job is his and he's gonna have about six weeks, right, and if he comes back in May, by mid June, if he's hitting one eighty one ninety and the power isn't there, I think you got to look at you know, making a deal or or you know, uh trade, some kind of a big trade, deadline acquisition. We have seen Corey Seeger's name kind of in the rumors, and we know that Texas is kind of breaking it down. But again, that doesn't solve your left handed, you know, being too left handed problem. So I don't buy that necessarily unless there was some kind of a deal in which they were also willing to give Josh Young, maybe take back a you know, Ryan McMahon, that type of thing. Like one thing that Cashman will do is surprise you with some creative, kind of blockbuster trades. They're not always good, you know, Donaldson taking him on to get Isaiah Kinder Fileffo was not really the smartest move. They were banking on ikf being a great shortstop that didn't have happen, uh you know, but you know there was the Jesus Montero, the late Hazus Montero for for uh, for Michael Pinada one year that came out of nowhere. So he will surprise you with some some random trades, So don't be shocked if he goes out there and gets a shortstop.

00:15:15
Speaker 2: One of the things that Cashman talked about at the winter meetings was the fact that they feel good about their bullpen with Bednar, the pickups that they made. You know, they kind of made their bullpen moves during the trade deadline and Camilla Duvall. Are they still short because they got they didn't get. They didn't bring back Devin Williams, they didn't bring back Luke Weaver yet. I think maybe there's a possibility of a reunion there, but where is that bullpen? Obviously we know where it's at currently, But can they not dip into the deep market because now the market the top guys are gone Suarez, Devin Williams and and Edwin Diaz. So are they going to dip into the next level of deep market in there or do they have their two pieces and they're just gonna fill in Well.

00:16:02
Speaker 3: I think that there's some interest in Trevor McGill from the Brewers, hard throwing righty, if you believe Ken Rosenthal and Will Salmon, which I do. The Yankees are also in on Freddy Peralta. This is another one of those areas where I could see kind of getting multiple birds with one stone kind of situation, trying to get Peralta and McGill and then maybe some of those pieces you mentioned earlier going back in a trade. Look, Milwaukee's scouting is so good I would expect any deal that we make with them for them to rake the Yankees over the coals in terms of prospects. But the Yankies also have some really good young arms that are, you know, starting pitchers in the minor leagues. But that are power arms. You know Elmer Cruz, you know Ben Hess, Bryce Cunningham. We have seen them use starting pitchers as relievers in the major leagues before, and they say, there's, you know, no such thing as a relief pitching prospect. A lot of times it's failed starting pitchers, and these guys aren't necessarily failed, but they're they're guys who could solve a problem cheaply with ninety eight on our fastballs and maybe one good off speed pitch. So I think there's a chance the Yankees might try and build internally with their bullpen. They might look at guys who are cast offs. I don't see him going out and spending big on a relief pitcher, but I could see them if they make a deal getting McGill.

00:17:18
Speaker 2: All right, If McGill is the guy, and you're talking about a team coming from a team that produces closers, that's just what they do. From a hater to Devin Williams, the McGill they get value for him. It's also a team that wants to win. I know he's your guy, but do you give up Ben Rice for McGill? Straight up, No, I don't think I would make that deal. I think Ben Rice is your starting first baseman next year. The metrics are really gone, and if he learns how to hit left, he is a little bit better. I mean, this is an all star. The Yankees kind of view him as a Kyle Schwarber type of hitter, like a guy who could eventually hit forty plus home runs a year, and I agree with him. And as a lefty and Yankee stadium, he's just too dangerous. I think I would rather see them go with some kind of other creative move and fill out the bullpen rather than having it to deal Ben Rice. I just don't think that that's a move.

00:18:11
Speaker 3: And when you're talking about Miguel is a guy who has had a flex restrain, which a lot of times can indicate, you know, stress on the elbow, which maybe is a precursor to Tommy John. Just anecdotally, I'd be worried about trading a reliable, up and coming power lefty bat for a guy who you know throws one hundred and two but could get hurt at any point.

00:18:33
Speaker 2: All Right, I set you up for that one because I knew you would say Ben Rice, no, just like you would have said Jason Dominguez, a few years ago. No, you can never touch my Jason. Yeah, Spencer Jones. Then all of a sudden, he's the one guy you hear he's untouchable. He's running out of time in the minor leagues. Is it Spencer Jones? Straight up? Because that's a big league player. It's a big league hitter. Of the adjustments he's made that the Milwaukee Brewers will say, here you go, good luck, here's six hundred got bets. Yeah.

00:19:01
Speaker 3: Well, I had Josh Norris from Baseball America on my show about a week ago, and he was not very high on Spencer Jones and rated him at the bottom of the twenty eighty scale in terms of his hit tool. He rated him a twenty And so you know, if you believe that, yeah, I would. I would move Spencer Jones. I mean, you're looking at like high thirty strikeout rate in the minor leagues. You guys know as well as I do, that strikeout rate doesn't typically go down when you go from the major from the miners to the majors. I know he's got power. I know he's been compared to a left handed Aaron Judge. I've always said that that's unfair but you know, I would have no problem moving Spencer Jones if it meant improving the big league club.

00:19:40
Speaker 1: Derek last one, And I know you touched on this on an episode a couple of weeks ago, but just for our audience to give them a taste of not only what you said, but then also what you've heard from the Yankees community. What were the thoughts on hal Steinberner saying that the team was not that profitable. I'm sure that was a tough one to swallow. It's one thing to talk to each other off season about, you know, where you're at with budgeting. I think everybody understands that. For me, as a media member, I was personally offended when he's trying to go over like what revenue versus profit is, Like most of us get it, including the person that asked the question. That's not what they were asking.

00:20:14
Speaker 3: Right, So there was a few a few things about me that about that that bothered me. He complained about the one hundred dollars tax bill or one hundred million dollar tax bill in the city, which is kind of a sweetheart deal, you know what I mean, Like that's the cost of doing business on the most expensive real estate in America, right, I mean.

00:20:35
Speaker 1: And I heard it's not one hundred, by the way, Derek, I heard it's more like eighty. And again, I know it's a big deal, but I heard it's like eighty. And it actually if you listen to David Samson's show, who's really good on this stuff and used to be in an ownership group at the Marlins, he essentially said it was just the way of them not showing the public that they were paying for things, right like, because the Yanks were like, oh, we're self funded, Like it wasn't self funded, and Hal just said it himself.

00:20:57
Speaker 2: Yeah, the bite.

00:20:58
Speaker 3: I watched David Sampson a lot and I love his stuff, and he has been saying for a while that the Yankees are not that profitable. So I mean, maybe he's right, and maybe how is right. But if you're not profitable as the ownership of the New York Yankees, you need to get the heck out of the baseball business and sell it to somebody who will you know, I said, basically, you know if you inherit a Ferrari right, and you're just gonna drive it forty miles an hour back and forth to the grocery store. You probably got no business owning that Ferrari. Sell it to somebody who's gonna get out there and take it on the track and use it the way a Ferrari is meant to be driven. If if how is not making a profit and not able to compete with other teams like the Dodgers and like the Mets across town financially anymore, he should take that as a sign to hey, let's pass it on, right. I mean, I know it's his father's legacy, but his father, I think, was under one hundred thousand dollars in personal funds invested into the Yankees when he bought it, And you can easily sell that franchise for ten billion dollars right now. I mean, put everybody in the family on Easy Street for generations, right and let a group like the Goggenheims, let a big Wall Street firm take over. Just make sure that there's somebody who wants to win in charge. And I'm good with it. As as I said on my show a couple weeks ago, we don't care who pays the bills. We care who raises.

00:22:27
Speaker 1: The trophy, perfectly stated, And I actually think, yeah, if you and me took over tomorrow, we could fix that. If there's really a profitability issue.

00:22:37
Speaker 2: I don't get for the eighty million dollar tax bill.

00:22:42
Speaker 1: I think you can if you see the revenue coming in On the other side. There's a lot of things that happened behind the scenes. Most owners have you know, they pay themselves, they pay others around them.

00:22:51
Speaker 3: There are a lot of.

00:22:51
Speaker 1: Things that you could clean up pretty quickly. Just I'll give you one quick example. John Angelos, who used to be running the Orioles after his lay father Peter passed away and then they sold it. He was paying himself five million dollars to run mass in the TV network. He knows nothing about that. He doesn't do much with the network that alone, right, should just tell you how some of the money gets hidden and how you're able to take it out of certain ventures that you have, Just to give like one taste of how things work behind the scenes. We're never going to see the books. I just it bothered me when I heard that.

00:23:20
Speaker 3: I think there's probably a director of financial loopholes somewhere within the Yankees organization whose only job it is to find those financial loopholes.

00:23:28
Speaker 1: As there should be Derek. Great catching up man. Have a great holiday everyone. Check out plenty of content coming from Pinstriped Territory Derek follow all the socials too, and Derek will be popping on Live whenever it is for breaking news when the Yankees do things. Thanks to you, Good to see you man.

00:23:45
Speaker 3: Happy holidays guys,

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