Jason Ross

This is generally how I'm viewing the meetings as well. I think the Cubs are a "groundwork" team at the meetings and less of an "action" team at the meetings. For example that Kyle Tucker trade - I think a lot of leg work for that was done in Dallas last year. So whatever the Cubs do this offseason, I think the leg work will happen Monday-Wednesday but the fruits will pay off later. My guess is close to yours; I think we'll see one reliever added, the Cubs will be connected to at least one very fun name in one way or another (think like a Nightengale post that suggests the Cubs have had conversations with Detroit over Skubal) that never goes anywhere, and maybe a report that they met with Boras and Imai. Beyond that, I think the actionable items will be the week leading into the holiday where we see the trade they were really working on or the Imai signing pop.

Image courtesy of © Kamil Krzaczynski-Imagn Images For many consumers Black Friday and Cyber Monday signal the time period in which it is time to "shop until you drop", buying holiday gifts and presents for the people we find important in our life. While MLB team's don't have a Black Friday discount sale, they do have their own version of a spend-a-thon, and it's during the annual Winter Meetings. Every year, teams, agents and players gather for a few days in December, and because of the proximity to each other, many of the year's biggest free-agent deals and trades are consummated at this event. Last year, for example, Juan Soto signed with the New York Mets on the largest contract in professional sports history while in Dallas for the 2024 version of the Winter Meetings. Though that won't happen again, what this means is that the Chicago Cubs will likely take part in some of this action next week. What, then, should we expect from the North Siders? When: Monday, December 8th - Wednesday December 10th Where: Orlando, Florida Great news for anyone (like myself) who lives on the East Coast! Trades, signings and the like sometimes break at late hours during the Winter Meetings, and in years' past, when they have been held out West, it wasn't uncommon to wake up to breaking news. Just last year, the news that the Cubs signed starting pitcher Matthew Boyd broke at 3:21 am EST. So, while we shouldn't expect the action to entirely die down at night, we're probably in for a slightly-less-late new cycle than when they meetings have been held in San Diego or Dallas. Monday and Tuesday will be full of rumors, and Wednesday will have its' fair share of smoke, it will also be the day of the league's annual Rule 5 Draft, in which teams will begin to fill out their 40-man-rosters from other team's minor-league ranks. Not all is lost after Wednesday, as a slew of moves will happen afterwards, with the groundwork for them being laid over the course of the previous few days. A good example of this: the Cubs' eventual trade for Astros' outfielder Kyle Tucker, which happened shortly after the close of last year's Winter Meetings. How should you follow the action? Social media is your best friend and worst enemy for this. If you know who to follow and listen to (either on X/Twitter, BlueSky or YouTube) you can be among the first of your friends to break the news that something went down. Any of the big names, such as Jon Heyman, Jeff Passan, Jon Morosi, or Ken Rosenthal can be highly trusted to post the truth (Bob Nightengale of USA Today is a little more hit-and-miss than others). Some of the more local outlets that can be trusted include Brett Taylor and Michael Cerami of Bleacher Nation (and, if you're looking for non-Cub sources, every team has their own version of Bleacher Nation!), Jesse Rogers, Dave Kaplan or Bruce Levine. Be careful out there, however. Smaller accounts with low follower counts could simply be clout-chasing for clicks or trying to purposefully deceive. A good rule of thumb: always look to see who's following these accounts. Do they have anyone you've heard of following them? No? Best to read things with a heavy hand of "skepticism" then. It's a fun time. Rumors are going to fly fast. Just be careful — some of the hardest to spot are the fakes who are just a letter or so different in their screen name from someone you really trust. Just be cognizant and keep an eye out for the false flags, but have fun following the flow of rumors, too. What are the Cubs going to do with their rotation? There's a good chance that the Cubs will look to solve the hole in their starting rotation during these four days. While it seems unlikely that Japanese star pitcher Tatsuya Imai will sign during the Meetings, most of the rest of the starting pitching market is likely to heat up now that Dylan Cease has set the market. Framber Valdez, Ranger Suarez, Michael King and others who may be on the Cubs' radar will likely come off the board soon. Some have fear with how much the team is willing to spend regarding a recent handful of cost-cutting measures over at Marquee Sports Network, also owned by the Cubs' ownership group, but those fears are just that: fears (as of now). If these fears are a reality, it may push the Cubs into a trade-scenario where they look into cost-controlled starting pitching such as the Miami Marlin's Edward Cabrera or the Washington Nationals' MacKenzie Gore. A trade may not fully materialize at the Meetings, instead taking a day or two beyond Orlando to complete (like their trade last offseason), so it may be a few days before we see the fruits of their efforts on this front come to fruition. Don't be entirely shocked to hear at least one crazy report connecting the Cubs to someone like Tarik Skubal, either. While it's far-fetched and the price would be astronomical, there are those who speculate he could be available a year prior to hitting his own free agency. Could the Cubs enter this sweepstakes? Absolutely, even if it's unlikely. The Cubs still need to fill out a bullpen, but who will they get? The team jumped pretty quickly into the reliever market, nabbing righty Phil Maton a few days ago on a two-year deal, but the Cubs are clearly not done filling out their thing bullpen. While they were connected to Ryan Helsley, he signed with Baltimore over the Thanksgiving holiday weekend, and reliever-ace Devin Williams is now off the board, taking his talents to the Big Apple, so the team is going to have to look elsewhere for help. A few names to follow in the back--of-their-pen search could be the Tampa Bay Rays' Pete Fairbanks, the San Diego Padres' Robert Suarez, or a reunion with Brad Keller. All three would require more than one year, but all three would add velocity and whiffs to a pen that needs it. Don't think the Cubs will only be looking for high-leverage help, though. Chicago needs to fill out their entire bullpen depth chart. They will probably look at some mid-level pitchers (i.e. Kyle Finnegan, Luke Weaver, etc), some left-handed pitchers to replace outgoing Caleb Thielbar and Drew Pomeranz, and some sleeper names, like reuniting with Mark Leiter Jr. or signing Evan Phillips, who is recovering from an injury and won't be ready until mid-year. When it comes to the relief market, I would assume anyone could be a fit. The Rule 5 Draft on Wednesday will also give the Cubs an opportunity to find some diamond-in-the-rough types as they look to round things out. In 2025, the Cubs selected Gage Workman, an infielder from Detroit, during this event. That did not work out for the team, but I wouldn't be surprised to see them find an arm they think they can mold into a useful bullpen piece. Are the Cubs looking to add to their offense? The Cubs are almost assuredly going to say goodbye to outfielder Kyle Tucker. The team does not seem interested in matching the free agent's price tag and instead appears happy to recoup the compensation pick. With young hitters Owen Caissie and Moises Ballesteros in the fold, as well, they seem poised to let the rookies take the designated hitter spot and run with it. That said, if the Cubs decide to go the trade route (moving, for example, Caissie in a trade for Cabrera) and move one, or both of their young hitters, could they find common ground with, say, Kyle Schwarber and bring the lefty home? Stranger things have happened! More than likely, however, the team will look into finding a Justin Turner replacement. Turner did post a 112 wRC+ against southpaws, but most would agree that his season left plenty on the table, and an upgrade would be in order. If the Cubs want another veteran, Paul Goldschmidt could make sense in this role. The team could also look to the IFA market, with two Japanese stars, Munetaka Murakami and Kazuma Okamoto, highlighting the class. Both offer power potential and the ability to play some first and third base. Neither projects as purely platoon options, and both would require commitments that appear to be well north of $15 million per year. Is the team looking to find someone who's capable of displacing Caissie or Ballesteros as their primary DH? Korean Infielder Sung-Min Song could be another intriguing IFA for the team. Song does not look to be as in-demand as his two Japanese counterparts, but offers a better glove and some surprising pop. The lefty wouldn't solve the team's platoon issue, but could add a fun option off the bench. The Winter Meetings will be a time in which, at least, some of these questions are going to be answered, but don't expect them all to be solved. Regardless of what happens, the Cubs will likely make a move or two. Matthew Boyd was signed last year and the framework for Kyle Tucker laid. Will this be as fruitful of a year? For the Cubs' sake, hopefully — the team cannot rest on their laurels and squander the 2026 season coming off a 92-win year. The time to add and improve is now. What do you think the Cubs will do during the Winter Meetings? Would would like to see them do? Sound off in the comment section below with your personal hopes, wishes and wants! View full article

It sucks out there. Frankly, I wish we could even go back to just a simpler time where we all were at least okay with saying that the Nazis were the bad-guys and not think twice-about-it.

Hey I support all of this. I can assure you, it's a hard line for myself to follow. I teach the Constitution to 8th graders every year. Reconciling how I feel as though our government and ideals are currently being stepped on, knowing that baseball players I root for support that stomping but also writing and podcasting and just loving baseball is a place I find impossible to find where I'm 100% happy with. Sadly, I'm not sure there is a place I could find where something isn't being stepped on.

Yeah, I get that. I think if we're talking about it as a purely human standpoint, if you disagree with his leanings, then that is fair. I have a hard time reconciling that, myself. Where I've come down on it is that; 1. I'm sure I disagree with many, and maybe a vast majority of baseball players on their leaning 2. Michael Busch, while he didn't take time off, was also photo'd with Kirk and I don't think I want to trade him So I'm at a crossroads where I find it hard to root for him as a human, but once I start getting to that point, I know that I'd probably have to throw the baby out with the bathwater, too, if I wanted to be consistent.

A reminder to everyone that Matt Shaw had a 130 wRC+ post ASB and after his largest mechanical change. His poor 8 games in the playoffs seems to be really weighing on everyone here. His wRC+ was better than Suarez, or Bregman, for example in the second half. Kim was terrible all year at the plate. Song does not project as an MLB starting player. As well, the Cubs finished top-5 in runs scored and even were a top-10 offensive team when Tucker struggled down the last two months. Beyond just that, these same discussions were had about Pete Crow-Armstrong last year and he rewarded the team with a 109 wRC+. We're jumping the shark here. Shaw doesn't need replaced as a starting player based on merit; he as roughly league average even if you just go back to May. He's better than a super sub. Yes, the Cubs should plan with a strong bench as @RandallPnkFloyd says, but a strong bench does not mean relegate Shaw to the bench, especially when the team needs most of the money invested in pitching.

There was at least a report recently that made it seem Imai was going to be taking visits this week and then signing at the Meetings. So if that's true, it would at least, hopefully, give the Cubs a second chance at biting the free agent apple if he comes off quicker.

Sigh. I probably would have done that deal. Here's to hoping they can either retain Keller or grab Fairbanks. Either would help complete the back end of the bullpen.

Michael Busch posted an 81 wRC+ against LHP last year. That's terrible. Now, there was some development late in the year, he hit a few home runs, and post June, there's some signs he's turned a corner. After June 14th, he had a 113 wRC+ against LHP, but it was done in 59 PA's. Generally speaking, this is not enough sample size to even say every data point of his is beyond the "stabilization" point (stabilization is when a data point is no longer affected by random outcomes). We also have to realize those were curated and heavily-data-induced PA's for the most part; they were specifically chosen for Michael Busch; he wasn't facing the best lefties very often. What this means is this: you can say that you'd like to see a little more of Michael Busch against LHP; I do too. Nothing, however, suggests the Cubs should just shrug their shoulders and not have a very defined platoon partner for him, too, Just because he gets more PA's does not mean he will be better; he will face more difficult LHP and his swing has changed in ways that helps more against RHP than LHP. Being a platoon hitter isn't a bad thing or a boogeyman now a days, it's just what a lot of players are. It's okay. Maybe he will become better against LHP but 60 PA's shouldn't signal a seismic shift.

Yeah, I'd sit with him in the one year mold. The split finger thing probably works for a year and you can likely re-mix more fastball heavy here or there to crate confusion and surprise. The Cubs have had success on primary fastball-splutter types like Shota (rotation) and Leiter Jr (bullpen) so I think they could probably find a good place for him. I wouldn't go insane if they didn't sign him, but he feels like a good one year reliever.

He is actually really good. I'd implore you to read all that, it would likely change your mind His issue isn't that he isn't good. It's that the Nationals are stupid.

Sure. But you didn't say "Hector Neris" you said the 2023-2024 bullpen. Yes, Neris was bad; the bullpen wasn't. Not every reliever will work out. Zombro is not a CC hire; he is an organizational hire. I also don't know why we wouldn't trust a David Ross hire. Where do you think Tommy Hottovy came from? He was here under Ross, too. Blowing leads is not really a great data point. Here's the thing; you can't blow a lead unless you have a lead, so good teams blow leads. The Dodgers, in 2023, had the 6th most blown leads but were a top-4 BP in terms of ERA. So I'm not sure any of that is useful data.

1. You answered most of your own question. 2. Tyler Zombro was not apart of the Cubs organization in 23-24 Also it should be noted, all of the complaining about the 2023 BP or the the 2024 BP: the Cubs had the 12th ('23) and the 13th ('24) best BP per ERA. The idea that the BP was a disaster in either of those two seasons does not bare fruit. Now, you *can* point to a lack of K's in the bullpen, and that they out-performed their xFIP, but you can also point to them as reasons for praise; they were able to get over performance and use their defense, so it's a bit of a "6 in one hand, half dozen in the other" argument.

The Cubs had the best BP ERA in May. So that's not true. It started to pay off starting about Mid-April once the Cubs moved on from Pressley as their "main" closer, shifting to a "committee" situation, and once they were able to switch out folks like Julian Merriweather.

Image courtesy of © Matt Marton-Imagn Images Kyle Finnegan is a name that has been floated and connected with the Chicago Cubs dating back to last offseason, when he was non-tendered by the Washington Nationals. As the trade deadline approached in the summer of 2025, his name was once again floated by Patrick Mooney and Sahdev Shama of The Athletic as a name the team was interested in. Instead of ending up on the North Side of Chicago, the Nationals instead dealt him to the Detroit Tigers. Now, as the Cubs look to rebuild their bullpen this offseason, the reliever could once again fit into the team's plans. Finnegan, 34, is a bit of a late bloomer, with his first full Major League Baseball season coming when he was already 29 years old. Between 2021 and 2025, the right-hander has been a solid bullpen arm, providing 2.2 fWAR over 322 innings pitched. If there is a bit of a knock on the former Nationals closer, it is that he's always been a bit home-run prone, giving up at least nine per year, and maxing out in 2023 with 11 round-trippers surrendered. For the Cubs, this may be less of an issue than for other teams, as Wrigley Field has done a great job suppressing offense all on it's own. Between 2023 and 2025, Wrigley Field has ranked 25th in offensive run value according to Baseball Savant's park factors, as well as below league average for home runs surrendered. There will still be days where the wind is howling, but it seems that the winds have literally shifted in on this front. However, the Detroit Tigers may have done the heavy lifting for the other 29 MLB organizations already by helping Finnegan change his pitch mix. Finnegan has plenty of velocity sitting between 96 and 97mph and a plus fastball shape according to FanGraphs' Stuff+ pitch modeling, but the pitch has been hit fairly well over the last few years, finishing with wOBA's against of .299, .339, and .349 over the last three seasons, respectively. Contrast, then, the reliever's other main offering, his split-finger, a pitch that has had, over the same span, wOBA's against of .254, .271, and .184, respectively. It grades out incredibly well by Stuff+ as well, and gets tons of whiffs—nearly 35% of the time in two of those three seasons. It's a great pitch, which makes it all-the-more-baffling that while with Washington, he threw the fastball nearly 70% of the time. Finnegan was able to remain a good pitcher, but there was meat on the bone that was being tossed in the trash can. This all changed last summer after being acquired by the Detroit Tigers who, over the course of two months, flipped his pitch usage. By the end of the season, Finnegan was throwing his split-finger fastball nearly 60% of the time, up from his 30% with Washington. This transformed the right-handed hurler from a good reliever to a near-elite one. Look at the difference between his time in Washington and Detroit in 2025: Finnegan saw improvement across the board (outside of hard-hit percentage). It shouldn't be shocking that featuring his best pitch significantly more, and one designed to increase ground balls and decrease fly balls. would be all that was needed to generate a major jump in the reliever's profile, and yet, Washington couldn't figure this one out. None of this is to say I would expect him to remain a sub-2.00 ERA pitcher moving forward, but that with a heavy dose of split fingers, he's likely going to be a significantly better option that he had been with the Nationals. The best thing about him, however, is that he won't break the bank. The right-hander did not feature in the Top 50 Diamond Centric Free Agent Rankings, and with his age-34 season upcoming, likely won't require a multi-year commitment to secure his services for the 2026 campaign. Knowing how the Cubs enjoy building their bullpen and their reluctance to fly above the luxury tax limits, he would fit nicely into their structure and would likely provide a strong back-end piece with Daniel Palencia and Phil Maton already under contract. He may not be as exciting as someone like Devin Williams or Robert Suarez at first, but could emerge as the steal of the offseason if he can keep up his momentum from Detroit. What do you think of Kyle Finnegan? Would you approve of the Cubs adding him to their 2026 bullpen? Sound off in the comment section below! View full article

Ahhhh Phil as in a team not a human being named Phil! I've been racking my brain as to which Phil in the Cubs org he was referring to.

Ben Brown was acquired by the Cubs in 2022, so they haven't been trying for 9 years.

It could come through trade but I'm not convinced of that. They have plenty of room under the LT remaining and they seem highly unlikely to spend much via offense. They also have ways of shifting money via their rotation (I.E. moving Taillon in a money dump like they did Bellinger last off season). As of this point last off-season, the Cubs had done very little and their interest in moving off Bellinger wasn't really all that obvious, Kyle Tucker was not on the radar and most thought the Cubs would go big on SP and they went towards offense. I don't think we will see such a drastic shift this year (they have made it clear it's about pitching) but they didn't follow convention last year either. We will see where they go from here. I think reading into anything in any direction right now is premature. Good chance what the Cubs do won't fall under whatever the general consensus is that they will do anyways. I just think there are a lot of people, and not saying this at you specifically, who are very convinced as to what the team's plans are, but I'm not convinced of anything. I think we will see more what happens later and until then, I'm going to leave any pathway of acquiring pitching as equally as likely.

I'm not sure he doesn't adjust to the market so much; he just doesn't really get irrational. That's always been my issue with him too! I really like Imai, probably moreso than others, so if he's going to get irrational, I've got hope that a 27-year old IFA with no draft pick compensation is "the guy". Ultimately, I'm sure it won't be however. He has a tendency to disappoint. More likely they go value with King and you hope they build a better-than-normal bullpen (not that they build bad ones, I just mean instead of a bullpen that's good but non-elite, one that leans closer to shut down from day 1) to compensate.

We really don't have any idea where the Cubs sat here. We have some Bruce Levine connections a few weeks ago and a Sharma/Mooney light connection but what the Cubs offered, how interested they are or what they're working on is all pure speculation. I wouldn't have minded the Cubs offering the deal Cease signed with Toronto. I wouldn't have minded a little stronger offer, but 7/$210 is probably very close to "market value" as you'll find for him, too. We don't have any "we tried" signals coming from Cubs media or Cubs sources. What that means is up to you and your analysis; it could be that they never really tried, that they found better value and pivoted to a different thing, or that they simply misread the Cease market. But I'm not really jumping on the "well the Cubs weren't willing to go above and beyond for Cease" thing...yet. We have heard the Cubs are interested in a higher level of P this year...I don't mind right now if it isn't Cease that they're after. There are a handful of pitchers who I would have in the same general category as Cease.

Eh, I think we are missing the forest for the trees in being upset about the reports they were interested. Lots go into that. We really haven't gotten the "we tried" stuff from the Cubs here yet, and maybe that's incoming, but it's been pretty quiet other than some reports early that the Cubs liked him. It sucks we didn't get Cease but it's also very early in the off-season. If the Cubs walk away with one from the Imai, Gore, Ryan, Cabrera camp I'm going to be fine regardless. I might even be cool with Michael King as our best SP addition but the rest of the off-season would have to offset the drop in my confidence there. There might even be a few names in this group we don't know are available but who are actually available. Long off-season. I'd have been totally cool with a 7/$210 for Cease, but that it was Toronto is what it is. Lots of options, lots of routes. In a vacuum the Cubs are fine. No reason to panic yet. Talk to me in January, though.

7 years for the type of pitcher Cease is, is fine. Contrary to popular belief, SPs are aging better than hitters. There is always the concern of the TJS bomb in there, but science has come so far on that surgery that it's a speed bump more so than what it used to be. Cease has been very available for teams as well. Sucks it wasn't the Cubs here.

He added a new pitch last year and refined his fastball location. I'm not very worried about the walks moving forward.