The 2025 Cubs could be deemed a big success. They won 90+ games for the first time since 2018, made the playoffs for the first time since 2020 and advanced a round in the playoffs for the first time since 2017. They even took the No. 1-seeded Brewers to the limit in the NLDS before losing in Game 5.
The 2025 could also be deemed a bit disappointing. They had a 6 ½-game lead in the middle of June and ended up losing the division to the Brewers by five games. They then lost to Milwaukee in the NLDS too.
Is that acceptable? I’d say that overall the season was successful but settling in line behind the Brewers isn’t where the Cubs should strive to be.
As such, the goal for club president Jed Hoyer this offseason needs to be to partially stay the course in fielding a winning ballclub while getting a bit more aggressive in trying to be great instead of just good.
Needs
If you look at the offensive depth chart right now, one could argue that the Cubs could just stand pat and would have a decent-to-good team. There isn’t necessarily a glaring hole unless you believe that Moisés Ballesteros can’t handle the DH full-time.
Remember, Kyle Tucker is a free agent. Also, it’s reasonable to believe that Pete Crow-Armstrong just had the best offensive half (the first half, for those who didn’t pay attention) of his career. Seiya Suzuki probably hit for more power in that first half than he could be expected to do moving forward, too. If those things are both true, in looking around the rest of the batting order, this team needs more home run power to get to where they need to go.
The rotation feels similar. With Matthew Boyd, Cade Horton, Jameson Taillon, Shota Imanaga (who returns after accepting the qualifying offer), Colin Rea, Javier Assad and the returning Justin Steele — at some point, as he’s coming back from Tommy John surgery — the rotation is technically full and isn’t bad.
Is it really good, though? It sure seems like a major-market team like the Cubs that sits right now in the mid-teens in payroll could go out and get a frontline starter for nothing more than money.
Then there’s the bullpen. From the core relievers that we saw taking on high-leverage roles in the playoffs, Brad Keller, Caleb Theilbar and Drew Pomeranz are free agents in addition to Michael Soroka, Aaron Civale, Ryan Brasier and a few others. Daniel Palencia returns and maybe Porter Hodge holds onto a setup role this time around, but otherwise it’s again a work in progress.
The Cubs have plenty of room on their 40-man roster right now. They need to build out a bullpen, add depth in frontline talent to the rotation and build a more powerful offense. There are a lot of avenues to get there and there’s a good foundation in place. It just isn’t great. And after missing the playoffs four straight years for this build, is good really good enough?
Possible targets
My hunch is there’s no chance the Cubs bring Tucker back. If they believe he’s not going to age well, perhaps this is the right move. My issue is that it isn’t that and instead it’s just “he’s too expensive” as the Cubs continue — at the behest of owner Tom Ricketts — to operate as a mid-market team when they should be a heavy hitter. Even if not like the Dodgers, Yankees or Mets, there’s no reason the Cubs couldn’t operate like the Phillies.
Alas, it sure seems like the Cubs want to be closer to 15th in payroll than fifth. That means Tucker is out.
As things stand, the Cubs have an estimated payroll for 2026 of $150 million or so. They were at nearly $210 million last season and just made the playoffs. So while we shouldn’t expect a $300 million payroll, there’s surely money that could be spent.
Maybe Alex Bregman ends up as a fit here. Third base is taken for the moment, but the offense needs upgrades and he represents one. In looking for a power upgrade, perhaps Pete Alonso sits around in free agency for a while and the Cubs decide to give him the DH spot (and he could play some first base with Michael Busch serving as DH at times, too, to keep both as fresh as possible).
Of course, there’s a monster power hitter who could fill DH and Cubs fans are very familiar with him. I don’t think it’s going to happen for multiple reasons, but the Cubs could sure use Kyle Schwarber. The power question gets answered rather easily right there.
Also, corner infielder Munetaka Murakami has been posted and has serious power.
We heard plenty this past year about the Cubs trying to trade for arms under team control for another year or two. On that list would be Joe Ryan of the Twins (the top option!), Sandy Alcantara and Edward Cabrera of the Marlins, Mitch Keller of the Pirates, MacKenzie Gore of the Nationals and a few others.
If the Cubs look to free agency for a guy who could serve as a frontline starter — and we know they’ve loved lefties in recent years due to how Wrigley Field plays — they could look to Framber Valdez or Ranger Suárez. If they went for a righty, Dylan Cease and Michael King are available. Zac Gallen could be a reclamation project not unlike the Cubs did on the position-player side with Cody Bellinger a few years ago.
Further, right-handed starter Tatsuya Imai from NBP is being posted and the Cubs have already been connected in rumors.
As for relievers, my guess is Hoyer continues to try and hit on bargain buys like he did with Keller, Theilbar and Pomeranz last season. It can work. It can also fail miserably.
There’s little doubt with the extra 40-man roster spots and money to spend that the Cubs will build out a deep MLB roster. The question is if there’s enough high-end talent to topple the Brewers and become a major player in the National League the way the Dodgers and Phillies are.
Possible trade chips
I mentioned Bregman as a possibility. If the Cubs are going to do that, third baseman Matt Shaw could be traded. He had a very good second half and there are plenty of teams that would give him a shot.
In that same vein, young outfielder Owen Caissie and/or young catcher/DH Ballesteros could also be floated in trade talks if offseason moves put established big-leaguers in front of them on the organizational depth chart. They’ve earned the right to get an extended look in the majors instead of toiling in the minors.
Further, I wonder if either Suzuki or Ian Happ could be traded.
Happ is only under team control for one more season and you pretty much know what you’re going to get at this point. He’s a 4-WAR player. He’s been between 3.5 and 4.3 each of the last four seasons.
Suzuki had his best half stateside last season followed by a miserable second half, but then woke up for the playoffs. He’s signed through next season as well.
If the Cubs wanted to sign Tucker (again, I don’t think they will), there’s an argument to be made to shed either Happ or Suzuki.
Finally, if the Cubs are able to grab a frontline starter, it’s feasible to believe that they could trade Taillon or another pitcher while also eating some money in the process.
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