North Side Territory: Previewing what 2026 may bring for the Cubs

Foul Territory

Looking ahead to a new season, North Side Territory hosts Sahadev Sharma and Patrick Mooney see a playoff-caliber team that’s approaching a cliff. With so many key players close to reaching free agency – and questions about the farm system and the baseball budget – this should be a fascinating year around the Cubs. Who stays? Who goes? What’s different from the organization’s last cliff? And why do some of these issues sound familiar?

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2025-12-28 26 min Transcript

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Transcript

00:00:04
Speaker 1: Welcome into Northside Territory. Foul of Territory Networks Cubs Podcast. I'm Sahadev Sharma with my partner Patrick Mooney. We are your Cubs beat writers over at the Athletic and Patrick, it is our twenty twenty six preview episode looking ahead to kind of the main storylines for twenty twenty six, and I think it all kind of comes down to one big team. Maybe this is a theme that you know, we'll be talking about all season long, but it's kind of you know, obviously, you know, don't want to go to negative town with this worrying about just go for it, to go for it twenty twenty seven holes. Who knows it's something we can deal with a year from now in all likelihood. But the specifically with the Cubs like this is that cliff that I mean, how how long is Like Jed and even before him THEO, they talked about these cliffs and there was a cliff coming up in twenty twenty one, and now it feels like potentially there's another cliff with Seye Suzuki, Ian Hap, Nico Horner, Jamison Tyne, you know, Carson Kelly, so many others as Matthew Boyd. There are a lot of pending free agents for this Cubs team, a Cubs team that is built to win right now, just made the playoffs and is looking to do that again. But I think, you know, what do they do to take advantage of a very clear two year window and also how do they make sure they avoid it being a cliff? What are what actions are they going to take? And I don't want to make it seem like they're devoid of talent. There's young talent on this team and that's something that twenty twenty one did not have. But there's a lot of talent up for you know, free agency that could be walking at the end of twenty twenty six.

00:02:11
Speaker 2: The cliff was I believe one of Jed's lines after the Darvish trade was that when he sort of called out the Tigers, Phillies maybe another organization of this idea of sort of running all the way to the edge of the cliff. And you know whether or not you're willing to do that, you know, at what point do you start to build something different and hopefully better. I think this group, I'm not going to call this some sort of like Last Dance. I don't think this group has accomplished enough. I don't think there's that sort of connection to the city the way that the prior group obviously had made an in double mark on franchise history, on baseball history like period.

00:03:01
Speaker 3: But I do think.

00:03:02
Speaker 2: It's kind of fascinating of just like, how do they manage that? And we're joking off air like it feels like a big trade should be coming, but we also felt that way like years ago. Yeah, obviously Kyle Tucker trade was obviously a blockbuster trade, but just sort of like but that was less kind of minor league talent that was more kind of moving. I guess Cam Smith just became major league so quickly that I'm already forgetting that part of it. But just this idea of like, you know, they had a you know, really strong farm system and some of them have graduated and performed in the majors.

00:03:50
Speaker 3: Matt Shaw, Kate Horton, Pete kow Armstrong.

00:03:53
Speaker 2: Do they do that or I mean, we're still starting on our spring training schedule, but I'm guessing there's gonna be some big names still out there, and I'm guessing we're gonna be covering free agency in Arizona again, because that seems to be the way the market has unfolded in recent years, and this out of the Cubs position themselves sort of like hanging around the basket, you know, trying to like get a put back at an easy, easy basket instead of setting the market and having the big show at the winter meetings.

00:04:26
Speaker 1: If they're adding someone like Alex Bregman, it feels like you have to make a trade that has to be coupled with the trade. Now I'm not saying it has to be an infielder. I'm just saying there's not enough. I'm saying it, whether it's by Astero's casey, Kevin Olcontra, like someone. These guys have to play. You can't just have them stay in triple A for the rest of their careers. Eventually their value plummets if you don't play them or move them. And we were getting to that point. I guess we're there where we're so you have to make some decisions here. There was you know, like Kevin el Contray, I think is an interesting name in the sense like this guy has high upside talent. There are talent evaluators that believe he can be a really good player. Where does he fit on this team? This is a guy that can handle center field. Well, he's not playing center field on the Cubs. At some point you have to get some value for a guy like that. If you add a bat, if you add Alex Bregman, who are you moving? What do you You can't just shift everyone to the bench or uh. It just like there needs to be something done. There needs to be moves made. I agree like it. When when's that big trade coming? You know, we saw them pull the trigger last winter. Curious if if that comes at any point this this winter, in the spring, where whenever it may be, I agree, I what I do wonder? I don't know. Maybe there's enough rumblings with Regman that that'll get done before the spring, but there'll probably be something that we're talking about. There's going to be a move. There's gonna be something still happening in the spring that we're covering. Uh And and the roster isn't fully settled by the time pitchers and catchers. It used to be you didn't have to worry about this stuff, and that era kind of seems gone. We'll see if the new CBA changes that at all. But certainly something that I feel like we're just going to be talking about uh for for a while here. And I think there's pressure on them to make these things happen, because, like I said at the start, like they have this kind of too. They even view it as a two year window. You know, this isn't something that we're kind of throwing out there. They see this. They they are aware of their contract status, they are aware of what's going on, what type of team they have right now. And I think it's interesting to think about some of the players that are coming up. I know he's not beloved by every fan, but Ian Happ is a career Cub and like, is this his final run with the Cubs, what does that look like for him? What kind of season can he put together? And of course the name, I think fans nobody, there's nobody that's in this fan base that has bad things to say about Nico Horner. I would guess a consummate teammate, consummate player, like the type of guy that you want on your team. We reported earlier this winter about you know, teams asking about him, and sure enough, there was a report in the San Francisco Chronicle by Susan Sluss. I believe that the Giants are asking about Nico Horner. It would make a ton of sense. He's from the Bay Area. You know they can he can help any team looking to win. For my money, I just don't see like a point in moving him. I get but again, when you're at this point with so many free agents coming up, you have to entertain these things. Any pending free agent, you kind of have to listen. That's a that's a very Cleveland philosophy, and CARTERI. Hawkins obviously has brought that with him from Cleveland. I don't think it's a bad thing to have an open mind. I do think it would look optically be really rough, and it may take a little while for anyone to see it at the fruits of a move like that. If it were to go down, Yeah, I think is really unlikely. By the way, I wanted just to emphasize that. I think we both feel this is a very unlikely thing to happen.

00:08:57
Speaker 2: Yeah, I am curious as the winter plays out, like could they trade someone on an expiring deal. I'm sure they'll entertain it. I still think that'd be a hard thing to execute. I still think Nico Horner or someone you probably discuss the contract extension with. I don't know if that's happened like that yet or if they wait, wait a bit and know that they'd probably have a pretty good shot at matching or getting something done in free agency as well. I still think looking at to kind of spring training, I think a Pete Chrom's from extension is something that.

00:09:38
Speaker 3: Will likely be discussed.

00:09:41
Speaker 2: I think it's that kind of window of spring training before opening day that's usually a time when teams and agents and players get together on those sorts of things. Once the arbitration site goes through, once those final free agents are off the board, you can kind of look internally, look ahead and do it in a way that you try and take, you know, the distraction off the table one way or another to get some sort of clarity or resolution. I believe it was around opening day in Tokyo last year when Pete was considering, you know, some some concepts. We don't have all the details, but that was a general timeline. And and then I think it also, I mean, you've written about this a lot recently to hot of like like dude, where's the pitching? And I think that'll be a fascinating, like kind of going back over our notes, I feel like we've covered a lot of different sort of iterations here of the Cups trying to figure out that pitching pipeline, and there has been progress, there has been success stories. There are different ways to do it, see the twenty sixteen World Series.

00:10:55
Speaker 3: So we're not you know, think about this one dimensionally.

00:11:01
Speaker 2: It's just kind of kind of obvious that there's not a whole lot coming.

00:11:07
Speaker 3: And maybe that's fine.

00:11:07
Speaker 2: If Kate Horton like contends for the Cy Young every year for the next six years, and Jackson Wiggins follows Horton's path and is pitching in the big leagues, pitching big innings, big moments in the big leagues this year, and they add a nice, you know, medium long term piece to the rotation via free agency or trade this offseason.

00:11:29
Speaker 3: All that could happen. But like they they've acknowledged that it it's an issue.

00:11:36
Speaker 1: Yeah, it's interesting how quickly it happened. There were some names that I think, you know, it had been traded over the past couple of years. They're not they haven't turned into top prospects, but they were valuable enough to be you know, used in trades. Ty Johnson comes to mind, a guy that they moved to get Esach Paratis. I'm probably missing a few. Uh, there's but there's been arms that have been traded that are like, oh, that's an interesting guy. Oh, look, he added five miles per hour to his fastball over the past three years. Those guys don't exist in the system. It's Jackson Wiggins. Then a steep decline and talent. Something that I had heard was the Cubs were like a bottom five team this past season and velocity gained. That was something that they changed drastically under Craig Breslo. This was a focus. This was something that was a major issue with the Cubs during you know, the THEO years, during their best years, and it was a complaint within the organization. They're bringing in guys and nobody's adding stuff, nobody's adding velocity. Where is the player development? And I don't know if it's like one thing leads to another, Craig Breslo leaves, this happens. It's hard to pinpoint exactly what went wrong? Is this player development? Is this draft? There are things that I've heard from outside the organization that you know, like I don't love these drafts. I got a lot of that this past draft of I liked their strategy, I don't know if I love the players that they selected in that strategy. Why where are the upside swings for pitching? You know, there's who's going to work with like or who where's the talent to work with? So you know that some things need to change and that they're making changes. I will say that was something that we didn't see as much, you know, in the previous years a last decade, as much of like there weren't changes made. It took a while before THEO finally made some sweeping changes. Uh and and now there are changes being made. And you know, I don't want to act like Tyler Zambro can fix everything. Obviously we've talked about him a lot on this podcast, and there's a reason for that. Like he's a he's a pretty big part of this front office, and he's being tasked with some pretty big things. I don't know if he can fix everything. I don't know how long it takes to make changes and and and get things on the right path. If he can get them on the right path, I will say he's respected in in the baseball world and and you can you can do enough that changes can show up pretty quickly. Uh. I felt like they did under Breslo. We we started to see almost immediate changes and and went from like, how come we never see a player develop, a pitcher developed? To here's Edward al Zalai, here's Justin Steele, Here's Keigan Thompson. You know, did all those players turn into great players and stars? No, but we just weren't seeing that. Javier Assad now Kate Horton, We'll see, we'll see where this leads. I think for me that they have acknowledged the issue, are aware of it, and are addressing it. That that's like you just need to see that. You can't like you can't be in denial that like things are fine. We have Kate Horton, Jackson Wiggins is coming, look at you know, we developed Justin Steele. You're not hearing excuses, and I think you know that that's that's what you want to see. You want to see them say like, Okay, this isn't going well enough for us, because if you're not developing pitching, it's the same thing. It's the same thing that happened, and it's sunk a much more talented core, you know, it sunk them. And this whole thing is being built on player development. If you don't develop talent, if you're not going to spend like the Cubs and flex your financial might, then you have to develop talent. So you got to get this right. And and I think there there's some uh, you know, what's the word I'm looking for. They're being aggressive about it, and and there's there's some fire here and they're trying to make things happen.

00:16:25
Speaker 2: Yeah, I think that previous career of Time Out had a little bit more talent, right. It was like basically the youngest core to like in a world series ever. And here we're talking about a core where like maybe roughly half the everyday players are going to be free.

00:16:37
Speaker 3: Agents right in in you know, several months. So, uh, I'm curious to see this year. You mentioned Justin Steele.

00:16:47
Speaker 2: H He is to me a fun pitcher to watch, just looking seeing how fans engage with him on social media. Him screaming in the dugout a couple of years ago in Milwaukee, I think he spoke for a lot of Cubs fans. I think it was his wake up you know, screaming. I think there's another word thrown in there and the return of showed to in Monaga. Like for me, I think I think it's that good year.

00:17:20
Speaker 3: I believe in what we've seen for.

00:17:26
Speaker 2: What like ten of his twelve months as a Cubs pitcher, you know what, over twelve months and over two seasons, whatever, however you want to break it down, I think the way Craig Council talked about him, how motivated he is. I think anyone who's encountered showed to understands where he's coming from. On that we've seen him make these adjustments before. You don't want to use injuries as an excuse, but if that set off a tiny chain, tiny chain change on that whole chain of mechanics that have to happen for him to be effective in the majors, maybe is a relatively simple fix. And if you have steel and showed a uh, you know, you go out and add another picture and an unidentified pitcher this offseason, we still't know who that is yet, boyd tie on Colin Ray like, I have a hard time seeing the twenty twenty sixth season going off the rails. I think they do have enough credible starting pitching.

00:18:36
Speaker 3: I think.

00:18:39
Speaker 2: The bullpen will frustrate people in April. Eventually they'll figure it out with guys we've never heard of before.

00:18:47
Speaker 3: And then just the.

00:18:50
Speaker 2: The Jed having his contract extension, Craig Counsel being one of the most established managers in the game, very professional group of players. I don't see it snowballing with like off the field stuff or distractions or personality conflicts like that does not mean the Cubs are winning like a hundred games and like dusting the Brewers. But with this extra wild card, like meaningful baseball in September almost feels automatic. I know it doesn't work like that in baseball, but I just have a hard.

00:19:30
Speaker 3: Time seeing them like losing ninety games or being on that.

00:19:33
Speaker 2: Sort of track you know where they where they sell the deadline like they they should be in it for the long haul here and then it's just a matter of being healthy again, right breaks And at what point do they sort of go outside their.

00:19:48
Speaker 3: Comfort zone and maybe do a big move that shakes things up.

00:19:54
Speaker 1: Yeah, I mean I agree on a lot of that, outside of injuries, you know, just hitting them hard. There is a core here and I know fans just think like losing Kyle Tucker means it's it's a huge step back, and you can't just assume that the young players take all take steps forward everyone stays healthy. I do believe that there's a lot of young talent here that can whole serve on on the offensive side, maybe not have a top five offense, but a top ten offense with you have to add on pitching. But I do believe that there's a step forward coming from from Kate Horton. What I saw from that guy this past season, Like he's the one that if I'm watching anyone in this staff, I agree with everything you said, Like I think showed a will bounce back. I'm excited to see what he can do. I'm curious to see how Justin Steal looks when he's healthy. But Kate Horton showed me something that I was just so impressed by everything both on the field and off the field, that I think something special is coming with this kid. I don't like being hyperbolic and saying, you know this guy, you know, just assuming stardom for young players when they show flashes, but it was the complete package, and that's why I'm impressed. He got better with each start. The strikeout started to come. You look at the overall numbers and you think he's not striking out enough guys. They started to come, and he learned how to pitch in the big leagues. He expanded his arsenal, like to do that all in one season, to add pitches, to use them differently, to learn how to command your pitches better, and what parts of the zone to attack hitters, and to have like these mental challenges. The Houston start, everyone talked about that, and and that did not sink his confidence. It made him tougher. I really have a ton of respect for the kid and think think special things are coming for him. And I think just on the offensive side, I really want to know, like I don't. Maybe we don't get an answer to this. Maybe up and down is his career. But Peter Armstrong, those two halves were so fascinating to cover, and just like that, that second half was a lot of questions spring up from that. And I don't think it's this is a disaster and he can't handle the moment as much as how does he learn from this? What kind of player can he be? How consistent can he get? Can he reach those highs a little bit more consistently and spread it out over a full season and what can he learn from the struggles and kind of bottle that up take those lessons. There's one thing that you know, like as as crazy as he can seem sometimes as like is undisciplined, I guess as he can see him at times, I think his teammates really like him and they know that, like, hey, look, it can sometimes be a little immature, and you know why, he's a kid. He's still young, he's still learning, but he's learning. He wants to learn. He wants to get better. He wants to how do I how do I improve in all facets of the game, whether it's on the field or smashing my helmet or you know, getting ticked after a rough at bat, whatever it may be. He wants to get better at all that stuff. And that that's something that I'm curious to see how that unfolds. And ultimately, I like, I think it's what everyone's waiting for.

00:23:35
Speaker 3: It's like what what is?

00:23:37
Speaker 1: And it's what we kind of started this with, like how do you what are you going to do to make this not the cliff? Like is it going to be some trade that adds talents. So now it's like okay, yeah, look yeah in in case he's taking a step forward, feel good about him stepping in at left field if that's the case, a right field for sayah by a steer your everyday dage say it's the kids. You go with a lot of kids. But is there a deal to be made to kind of extend like add some pitching and like, you know, cover the gap of like okay, well the pitching development isn't where we want it to be right now, but here's how we cover the gap. We got a young, controllable pitcher and him with Kate Horton and Justin Steele, we we have pitching for the next couple of years.

00:24:25
Speaker 2: What what is it?

00:24:26
Speaker 1: What are you gonna do? Are you going to sign Alex Bregman? And now you have Dancy Swanson and Alex Bregman as your cornerstone veterans?

00:24:33
Speaker 2: Is that?

00:24:34
Speaker 1: Are you going to extend Nico Horner? What is it? What are you gonna do? How are you going to extend this? So it's not the cliff, We'll see what it is. I don't know if there's a hard and fast answer coming in the next month. That'll be during the season what we're going to see, But it's a it's a fascinating season in so many levels. Obviously, we're going to be talking a lot about the CBA a year from now. Hopefully it doesn't eat into games, but you know, that's a depressing thought for another day.

00:25:06
Speaker 2: Yeah, we'll leave negative town and say thank you to all of our readers and listeners and the great behind the scenes people at the foul Territory Network who are on like twenty four to seven, always hustling to put out a ton of shows around the clock.

00:25:25
Speaker 3: And these shows don't happen without the passion.

00:25:29
Speaker 2: From our listeners and readers who give us this great opportunity to cover a team that people really care about.

00:25:38
Speaker 3: We see it in the numbers, and we thank you for your support.

00:25:43
Speaker 1: Yeah, thank you to everyone behind the scenes putting in all that work. Happy holidays to all of you. Thanks for listening. We really appreciate the support. It has been great to see you over the past almost two years now that we've been doing this show. Everyone really supporting this show and we're growing with episode and we appreciate you guys listening and spreading the word. Uh hope, hope to hear a lot more Cubs news in the new year, and we'll talk to you then. Well, no, we'll talk to you before the new year. We'll talk to you after Christmas time. Thanks so much for listening to everyone. Happy holidays and take care.

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