Are Cubs Buyers or Sellers This Offseason? Could It Be Some of Each?

We’re dangerously close to the end of the 2024 Major League Baseball season. There’s a certain disappointment that comes with that. But for the fans of the 29 teams that won’t be crowned World Series champion, there’s also a level of anticipation that comes with that. It’s interesting to think about where the Chicago Cubs fall on that spectrum.

After the last few offseasons, it’s easy to be dismissive of the potential outcomes that the winter of 2024-25 will bring to the North Side. A few marginal changes here, some reclamation-project relievers there. Even with some fairly significant contracts signed (Dansby Swanson and Cody Bellinger, most notably), it’s not as if there has been an earth-shaking move from the current regime at any point, whether via trade or free agency. Given that the same conservative group still rules the organization, that’s likely going to continue to be standard operating procedure in yet another offseason.

At the same time, there’s a world where the Cubs can become as interesting as any team in baseball for the next several weeks. The leaders in a massive market spending consecutive years on the mere cusp of contention isn’t acceptable, after all. We’ve reached the point where Jed Hoyer is objectively fighting for his job, given his contract status. That’s not to say that they’re going to dole out beefy contracts to Juan Soto and Corbin Burnes and Alex Bregman in an effort to “win” the offseason and preserve Hoyer’s place atop the front office. But there’s an opportunity here to be as active as they’ve been in any winter of the past several years.

We call this the paradox edition of the potential offseason outcomes, with a pathway to both buying and selling in an effort to get back into contention for 2025.

There are, of course, certain “locks” for the 2025 Chicago Cubs that go beyond contract status. Shota Imanaga, Justin Steele, and much of the team’s collection of young relievers on the bump (Porter Hodge, Ben Brown, etc.) should be retained. On the positional side, you’re probably looking at Dansby Swanson, Michael Busch, Isaac Paredes, and Pete Crow-Armstrong. These types of names go well beyond what’s on paper. They’re players who not only have a certain level of team control, but feature a skill set that you absolutely desire as a factor in the “next great Cubs team.” If we start to look too closely at contracts, then flexibility starts to dissolve before our eyes. Contractually, much of the 2025 Cubs are likely already here. 

Which is why our paradoxical version of the impending offseason is so much more fun. Instead of simply accepting the certainty that exists all over the roster and merely supplementing with a short-term focus on the next year or two, the Cubs can deploy a bit of creativity for a change, in order to build out the roster for success that stretches out a bit more long-term.

The Chicago Cubs currently boast a handful of quality veterans whose contracts run throughout the next two years. The team, as currently constructed, isn’t really in a position to hang with the genuinely elite teams of the National League in either 2025 or 2026. A couple of simple moves could put them into playoff contention, sure. But what if we start to look at improving this team over the course of that stretch, but also a bit past it? 

Perhaps that starts with trading Ian Happ—a player whose skill set I’ve come to admire greatly. This isn’t a suggestion that they should move him. But perhaps if you were to move his two more years of advanced approach and steady glovework—there would be many takers on the trade market, although he would be able to direct his own destination—you can shoot higher on corner outfield upside. As easy as it is to love what Happ brings, we also know what his ceiling looks like at this point. The idea here is that you could move his notable money off the books in order to raise that ceiling via a separate deal. 

Seiya Suzuki fits a similar bill on the positional side of things. His defense is a massive shortcoming, and it’s unlikely the team wants to limit themselves to a full-time player in the designated hitter spot. With only two more years on his contract, could a team take his bat in order for the Cubs to upgrade the other corner in a more comprehensive way?

It's not a dissimilar idea from potentially moving Nico Hoerner. Again, we know what he brings to the middle of the infield. But you’re looking at a certain offensive ceiling that could be raised without compromising too much on the defensive side. That could mean elevating a prospect, in the form of Matt Shaw or James Triantos. It could also mean shifting gears entirely and bumping Paredes over to the keystone, in order to improve your offense there while finding a higher-impact bat at third base.

If we wanted to propose such an idea on the mound, you’re likely revisiting the idea of trading Jameson Taillon. While he faltered at points, his total body of work in 2024 looks better than many of his career numbers. His best ERA (3.27) since 2018 & his best FIP (3.92) since 2019. A team looking to bolster its rotation in the shorter term could absolutely look to Taillon, in order to maximize their next two years.

Let’s quickly circle back to what’s not being suggested here. The idea is not that the Cubs would be better without any of these four players, absent further moves. Nor is the idea that any of the four would be moved in the exact deal for their potential replacement. The concept is that the Cubs have a handful of high-quality veterans for the next two years. But we’ve established throughout this season that the Cubs need impact on both sides of the ball. There is a world where the team could move at least one player noted here in pursuit of a separate deal in which they can find a legitimate upgrade that represents a longer-term play.

Of course, I don’t know what that player looks like. Beyond the free-agent market (which is sparse in terms of the type of talent the Cubs actually need once you look past the frustratingly unattainable Soto), we don’t exactly know who could be had for the right price via trade. Nor do we have a present idea of non-tenders. Not that a non-tender candidate is necessarily the type of player you look to in order to replace established vets. It's just one more source of uncertainty. You get the point.

Ultimately, the Chicago Cubs have a set position within the National League. They’re a fine team, but not necessarily a good one and certainly not an elite one. We’ve established before what they are, which is largely a collection of complementary bats in need of more impact sprinkled throughout their roster. With some of these two-year guys in tow and a high volume of covetable prospects, there’s a world where the Cubs can “sell” some of the quality veterans while pivoting to deals that feature higher-impact talent whose team control stretches beyond 2026. It’s not an easy world to perceive, especially in the face of prospect-hugging types. It's a little scary.

It also goes against the typical modus operandi of this front office, as it represents a more aggressive means of operating. It’s why we’re treating it as such a paradoxical idea. Trading your veterans to get better now, while making aggressive movement toward adding more impact to the roster. It borders on fiction, to be sure. But, man, it would be a fascinating sequence of events to watch unfold as we progress into the winter months.