No matter how you slice it, the Chicago Cubs were one of the most disappointing teams of 2024. Improved play in the second half enabled a winning record and a second-place finish in the NL Central, but the Cubs finished six games out of a wild-card spot and a whopping 10 games behind the rival Brewers.
At this time a year ago — before our collective focus shifted to star players such as Shohei Ohtani and Juan Soto — the baseball industry was in shock following the Cubs’ ultra-aggressive maneuver to hire manager Craig Counsell away from Milwaukee with a five-year, $40 million deal, the largest contract ever given to a big-league skipper. 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 have not reached the postseason since Jed Hoyer assumed the top front office role after Theo Epstein departed following the 2020 season, and they haven’t won a postseason game since 2017. Considering the talent on the roster and the massive commitment made to Counsell, such shortcomings can be tolerated for only so much longer. This organization must find a way to reestablish itself as a legitimate contender in the National League and quickly.
Here are the five biggest questions facing the Cubs this winter.
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1. Does Cody Bellinger actually fit on this roster?
“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 his player option to stay with the Cubs for $27.5 million in 2025. “It mostly just gives us clarity,” he added. “Now we know what our roster looks like, and now we can go about building a team. Before that, there was some uncertainty.”
Hoyer’s sentiment is reasonable on its face and an understandable one to share publicly. But there are two issues. For one, Bellinger’s second season in Chicago brought into question just how good of a player he actually is. Bellinger practically reinvented himself as a hitter in his first year with the Cubs in 2023, drastically cutting down on his strikeouts in favor of a more high-contact approach. While he kept the strikeouts down in 2024, he provided far less power, with his SLG% dropping nearly 100 points, bringing his overall offensive contributions closer to league average.
Arguably more pressing here is Bellinger’s fit defensively, as the two positions he has been known for playing brilliantly in his career — first base and center field — are occupied in Chicago by two ascendant core pieces in Michael Busch and Pete Crow-Armstrong. That means Bellinger currently projects as Chicago’s every-day right fielder, with Seiya Suzuki shifting to more of a primary DH role. While Suzuki’s bat is certainly good enough to produce like a high-level DH, Bellinger — especially at his salary — as strictly a right fielder is notably less appealing, particularly if his power production remains middling at best.
Combine these two factors, and it’s unsurprising that Ken Rosenthal reported earlier this week that the Cubs are trying to trade Bellinger but having a tough time doing so, due to both his uncertain outlook as a hitter and his contract status. Bellinger has another player option for $25M in 2026 that he could pick up next winter if he delivers another mediocre campaign, so committing to two more years of this lesser version of him is probably a tough pill for potential suitors to swallow.
All of this might keep his trade value at a suboptimal level, to the point that dealing him away isn’t worth more than moving forward with him as the every-day right fielder and hoping he rediscovers some power production. Another way to look at Bellinger’s decision to opt in is how it might’ve impacted Chicago’s willingness to spend in free agency this winter. Which brings us to our next question …
2. Will the Cubs pursue anyone 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 be playing in the deepest waters of free agency this winter. Whether that is directly related to having Bellinger back in the fold at a significant salary number is undetermined, but even with Bellinger, the Cubs’ payroll is currently well below $200 million, according to Roster Resource — nowhere near the $241 million competitive balance tax line that most big-market behemoths have flirted with or blasted past in recent years. There is unquestionably room for another big-ticket addition in Chicago without needing to pay the luxury tax, if ownership demonstrates an appetite for it, but it remains to be seen if such an appetite exists.
Early indications out of Boston — another massive market that has been more conservative with spending in recent years — portray a Red Sox team ready to spend aggressively and reassert itself as a premier franchise after several consecutive underwhelming seasons. One could argue that the Cubs should be acting in a similar fashion, considering their roster and recent history, but that’s not exactly the tone we’ve seen thus far. However, we’re still in the earliest 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?
Should the Cubs’ brass wake up someday soon with the ambition to chase the biggest names on the market, a pursuit of Corbin Burnes, Max Fried or Blake Snell would make plenty of sense — not to mention a run at Roki Sasaki, as quite literally every team should be making. But the Cubs proved last year with the smash-hit signing of Shota Imanaga that they can strike gold in the second tier of starting pitchers as well. 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 gamble on a shorter-term deal. 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 significant splash in free agency. Chicago made a nifty trade with Cleveland earlier this week, dealing 20-year-old outfield prospect Alfonsin Rosario to acquire right-hander Eli Morgan, who was quietly excellent when called upon as one of the less-heralded members of the elite Guardians bullpen. Morgan will help, but there’s plenty more room for upgrades in this bullpen. Perhaps the Cubs stay away from top-tier starting pitchers in free agency and instead focus on landing one of the elite relief arms available, such as Tanner Scott, Jeff Hoffman or Clay Holmes. The bullpen market is also stocked with veteran types who could fortify this unit; Blake Treinen, Kirby Yates or even Kenley Jansen come to mind. The Cubs wouldn’t have to break the bank to land these types of arms and could realistically also add a mid-tier starter to seriously strengthen the entire pitching staff.
With so much of the position-player group seemingly set — and with more help on the way — there’s no excuse for Chicago not to make several meaningful additions on the mound this winter.
4. Is the Cubs’ infield set, or are more moves coming?
Let’s turn our attention back to the offensive side of things and contemplate the infield. The surprise acquisition of Isaac Paredes at the 2024 trade deadline made an already crowded depth chart even more difficult to project moving forward and prompted some intriguing possibilities entering this offseason. That would’ve been true even if Paredes had raked for the Cubs post-trade, but that’s practically the opposite of what happened, as he didn’t perform anywhere close to his potential in the second half. Still, Paredes is under team control through 2027, and it’s not like the Cubs got him for free; trading for him seemed to signal a real intention for him to be the third baseman in Chicago for the foreseeable future.
Enter Matt Shaw. The Cubs’ first-round pick in 2023 out of the University of Maryland had a marvelous season in the minors, reaching Triple-A and excelling in 35 games to finish the season before he starred with Team USA in the Premier12 tournament. A shortstop in college, Shaw bounced around the infield in his first pro season but took the majority of his reps at third base, a position that seemed open in Chicago … until Paredes was acquired. We don’t know if Shaw is ready to contribute on Opening Day, but it’s not difficult to imagine a big spring training from the talented infielder creating pressure for him to crack the Cubs’ roster out of camp. But where will he play? This is a good problem to have on paper, but it becomes more complicated if Paredes doesn’t bounce back.
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 character here as well. Hoerner is under team control for two more seasons and provides outstanding defense but a bat that has plateaued around league-average. If the Cubs deem Shaw ready sooner rather than later, might they consider dealing Hoerner to make room for Shaw at second? It’s awfully difficult to determine whether that’s a sensible strategy without knowing just how big-league-ready Shaw is or what version of Paredes the Cubs will get in 2025, but it’s certainly a path worth exploring — especially if teams are willing to pay a substantial price for Hoerner.
5. Which prospects are the Cubs counting on to contribute in 2025?
Shaw isn’t the only prospect in the upper levels of Chicago’s system who could make a difference in the big leagues in the near future. As if the infield picture weren’t jam-packed enough, second baseman James Triantos — a wonderful defender with strong contact skills and plus wheels on the basepaths — also reached Triple-A in 2024 and could play his way into consideration next summer. Third baseman Cam Smith, Chicago’s first-round pick this past summer out of Florida State, collected more total bases than any other 2024 draftee after signing and finished the season in Double-A. He could be ready far sooner than anyone expected.
Catcher Moises Ballesteros had a monster breakout season as a 20-year-old, hitting his way to Triple-A and finishing with a strong few weeks in the Arizona Fall League. But the recent acquisition of catcher Matt Thaiss from the Angels suggests that the Cubs might not be ready to lean on Ballesteros as the backup to incumbent Miguel Amaya too quickly, though it’s possible that his bat forces the issue at some point in 2025.
Outfielder Owen Caissie was added to the 40-man roster this week and has massive raw power that was on display over a full season in Triple-A in 2024, but he’ll need to iron out some significant strikeout issues before getting the call to Chicago. Super-athletic 22-year-old Kevin Alcantara made his debut in the Cubs’ outfield 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 option in the short term. Caissie’s and Alcantara’s paths to playing time would’ve been much clearer had Bellinger opted out, but now each will need to prove his worth over a longer period of time in Triple-A to warrant consistent run at the big-league level.
Not all of these players will end up making an impact in Chicago. But their proximity to the big leagues and prospect cachet are worth monitoring as the Cubs sort out their roster for 2025, especially in the context of possible trades this winter and next summer.