No matter how you slice it, the Chicago Cubs were one of the most disappointing teams of 2024. Improved second-half play enabled a winning record and second place in the NL Central, but the Cubs finished six games out of the wild card spot and a whopping 10 games behind by the rival Brewers.
This time a year ago — before our collective focus shifted to star players like Shohei Ohtani and Juan Soto — the baseball industry was in shock after the Cubs’ ultra-aggressive move to hire manager Craig Counsell away from Milwaukee for five years. , $40 million, the largest contract ever awarded to a major league captain. That Milwaukee then ran away with the division while the Cubs were stuck in the mud for much of Counsell’s first season at the helm only made Chicago’s uninspiring campaign that much more frustrating.
The Cubs haven’t made the postseason since Jed Hoyer took over after Theo Epstein’s departure after the 2020 season, and they haven’t won a postseason game since 2017. Given the talent on the roster and the huge commitment to Counsell, such shortcomings can only be tolerated for so much longer. This organization needs to find a way to quickly and re-establish itself as a legitimate contender in the National League.
Here are the five biggest questions facing the Cubs this winter.
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1. Does Cody Bellinger fit on this list?
“Anytime a really good player decides to stay with you, that’s good news,” Hoyer said earlier this month after Bellinger’s decision to pass on another round of free agency and pick up a player option to stay with the Cubs for $27.5 million through 2025. “Mostly it gives us clarity,” he added. “Now we know what our roster looks like and now we can start building the team.” There was some uncertainty before.”
Hoyer’s sentiment is reasonable on the face of it, and it’s understandable that it can be shared publicly. However, there are two problems. First, Bellinger’s second season in Chicago called into question just how good of a player he really is. Bellinger practically morphed into a shortstop in his first year with the Cubs in 2023, drastically reducing his strikeouts in favor of a more contact approach. While he limited his strikeouts in 2024, he provided far less power, with his SLG% dropping nearly 100 points, bringing his overall offensive contribution closer to league average.
Perhaps more pressing is Bellinger’s defense, as the two positions he’s been known to excel at in his career — first base and center field — are occupied in Chicago by two up-and-coming starters in Michael Busch and Pete Crowe-Armstrong. That said, Bellinger currently projects as the everyday right fielder in Chicago, with Seiya Suzuki moving more into the primary DH role. While Suzuki’s bat is certainly good enough to produce as a high-level DH, Bellinger—especially at his salary—is significantly less appealing as a strictly right fielder, especially if his power production remains middling at best.
Combine those two factors, and it’s not surprising that Ken Rosenthal reported earlier this week that the Cubs are trying to trade Bellinger, but are having a hard time due to his uncertain prospects as a hitter and his contract status. Bellinger has another $25 million player option in 2026 that he could pick up next winter if he puts up another average campaign, so committing to two more years of this smaller version of himself is likely a tough pill to swallow for potential suitors.
All of this could keep his trade value suboptimal, to the point that dealing him away is worth more than moving forward with him as an everyday right fielder and hoping he rediscovers some power production. Another way to look at Bellinger’s decision to sign is how it may have affected Chicago’s willingness to spend in free agency this winter. Which brings us to our next question…
2. Will the Cubs pursue someone at the top of the free agent market?
On a recent episode of Baseball Bar-B-Cast, ESPN insider Jeff Passan mentioned that the sense in the industry is that the Cubs are not expected to play in the deepest waters of free agency this winter. Whether that’s directly related to Bellinger being back in line for a significant salary number is undetermined, but even with Bellinger, the Cubs’ payroll is currently well under $200 million, according to Roster Resource — nowhere near the $241 million mark from the competing tax balance. which most of the big market giants have flirted with or shot back in recent years. There is undoubtedly room for another big addition in Chicago without paying the luxury tax if ownership shows the appetite, but whether that appetite exists remains to be seen.
Early signs from Boston — another massive market that has been more conservative in spending in recent years — show the Red Sox poised to spend aggressively and reassert themselves as a premier franchise after back-to-back disappointing seasons. One could argue that the Cubs should act in a similar fashion, given their roster and recent history, but that’s not exactly the tone we’ve seen so far. However, we are still in the early stages of the offseason and things can change quickly. If the Cubs are going to spend more than we currently anticipate, it seems likely that something will be done to address the pitching staff. On that note…
3. The Cubs need pitchers, so which pitchers could be realistic targets?
If the Cubs bullpen ever wakes up with the ambition to pursue the biggest names on the market sometime soon, pursuing Corbin Burnes, Max Fried or Blake Snell would make a lot of sense — not to mention making a run at Roki Sasaki, as literally every team should. But the Cubs proved last year with the successful signing of Shoto Imanaga that they can strike gold in the second string of starting pitchers. In that realm, Sean Manaea and Nick Pivetta come with qualifying offers attached, but each offers substantial upside and won’t cost nine figures. The same goes for Walker Buehler, who could be a nice short-term gamble. Chicago also feels like an excellent landing spot for Shane Bieber, even if he won’t be ready to help right away next season.
The bullpen is another avenue for the Cubs to make a big splash in free agency. Chicago made a smart trade with Cleveland earlier this week when 20-year-old outfield prospect Alfonsino Rosario was able to acquire right-hander Eli Morgan, who was quietly excellent when called up as one of the less heralded members of the elite Guardians bullpen. Morgan will help you, but there is a lot more room for improvement in this bullpen. Maybe the Cubs stay away from top starting pitchers in free agency and instead focus on landing one of the elite arms available like Tanner Scott, Jeff Hoffman or Clay Holmes. The bullpen market is also stocked with veteran types who could bolster this unit; Blake Treinen, Kirby Yates or even Kenley Jansen come into consideration. The Cubs wouldn’t have to break the bank to acquire these types of arms and could realistically add a middle-of-the-pack starter to seriously bolster the entire pitching staff.
With the position group seemingly set — and with more help on the way — there’s no excuse for Chicago not to make some meaningful additions this winter.
4. Is the Cubs infield set, or are there more moves coming?
Let’s turn our attention back to the offensive side of things and think about the interior. The surprise acquisition of Isaac Paredes at the 2024 trade deadline made it even more difficult to project an already crowded depth chart going forward and prompted some interesting options entering this offseason. That would have been true even if Paredes had played after being traded to the Cubs, but that’s practically the opposite of what happened, as he didn’t show anywhere near his potential in the second half. Still, Paredes is under team control through 2027, and it’s not like the Cubs are getting him for free; Trading him seemed to signal a real intent to become Chicago’s third baseman for the foreseeable future.
Enter Matt Shaw. The Cubs’ 2023 first-round pick out of the University of Maryland had a terrific season in the minors, reaching Triple-A and excelling in 35 games to finish the season before playing with Team USA in the Premier12 tournament. A shortstop in college, Shaw bounced around the field in his first pro season, but got most of his reps at third base, a position that seemed open in Chicago … until the acquisition of Paredes. We don’t know if Shaw is ready to contribute on Opening Day, but it’s not hard to imagine the talented outfielder making a big spring training push to crack the Cubs’ roster out of camp. But where will he play? It’s a good problem to have on paper, but if Paredes doesn’t bounce back, it’s going to get more complicated.
With Busch entrenched at first base after a strong rookie season and Swanson locked in at shortstop for the long haul, second baseman Nico Hoerner becomes an interesting figure here as well. Hoerner is under team control for two more seasons and provides excellent defense but a bat that hovers around league average. If the Cubs consider Shaw ready sooner rather than later, could they consider trading Hoerner to make room for Shaw in the second row? It’s awfully hard to determine if this is a sound strategy without knowing how big-league ready Shaw is, or what version of Paredes the Cubs will be getting in 2025, but it’s certainly an avenue worth exploring — especially if teams are willing to pay significant sums. prize for Hoerner.
5. What prospects do the Cubs have in 2025?
Shaw isn’t the only prospect in the upper echelons of Chicago’s system who could make a difference in the big leagues in the near future. As if the outfield picture wasn’t loaded enough, second baseman James Triantos — a terrific outfielder with strong contact skills and plus wheels on the basepaths — also reached Triple-A in 2024 and could be considered next summer. Third baseman Cam Smith, Chicago’s first-round pick last summer out of Florida State, accumulated more bases than any other player drafted in 2024 after signing and finished the season in Double-A. He could be ready much sooner than anyone expected.
Catcher Moises Ballesteros had an incredible season as a 20-year-old, making it to Triple-A and finishing with a strong couple of weeks in the Arizona Fall League. However, the recent acquisition of catcher Matt Thaiss from the Angels suggests the Cubs may not be ready to lean on Ballesteros as incumbent Miguel Amaya’s backup too soon, though it’s possible his bat will force the issue sometime in 2025.
Outfielder Owen Caissie was added to the 40-man roster this week and has tremendous raw power that has been on display all season at Triple-A in 2024, but he will have to work out some major strikeout issues before he gets the call-up. Chicago. Super-athletic 22-year-old Kevin Alcantara made his Cubs outfield debut last summer after a much shorter stint in Triple-A, but he too will need to make more consistent contact to be considered a viable short-term option. . Caissie and Alcantara’s paths to playing time would be much clearer if Bellinger opts out, but now each will have to prove their worth over an extended period of time in Triple-A to guarantee a consistent run at the big league level.
Not all of these players end up making an impact in Chicago. But their proximity to the big leagues and prospects are worth watching as the Cubs work out their 2025 roster, especially in the context of possible trades this winter and next summer.