As the 2026 offseason unfolds, the Chicago Cubs find themselves in a state of cautious anticipation. During the Winter Meetings last month, Cubs president of baseball operations Jed Hoyer expressed a clear sense of activity and momentum across multiple fronts for the team. However, he also added a note of prudence, emphasizing that while the front office is actively pursuing improvements, they are committed to avoiding costly mistakes. Nearly a month into the new year and with Cubs Convention on the horizon, the team has made some moves but has yet to land a major splash in free agency. The focus remains keenly on upgrading key areas—particularly adding an impact bat and bolstering the starting rotation.
Current Offseason Status and Remaining Needs
Despite an active start, with approximately $30 million already invested in bullpen arms and bench players, the Cubs are still targeting critical upgrades. The decision by Shota Imanaga to accept the Cubs’ qualifying offer for $22.025 million, along with re-signings like swingman Colin Rea, has provided some rotation depth. Yet, the team is still on the lookout for a game-changing bat and a dominant starting pitcher—two priorities that could significantly influence their competitiveness in 2026.
While the team’s moves so far focus largely on depth, upgrading the lineup and rotation remains an ongoing puzzle. The front office’s strategy incorporates both free-agent signings and potential trades, taking into consideration the roster’s current composition and long-term flexibility. The next moves could shape the Cubs’ competitive window for seasons to come, especially as they balance immediate needs against financial prudence.
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Targeting a Key Bat in Free Agency
The Cubs have been linked to several high-profile free agents in their quest to add a potent offensive weapon. Among the most notable names in discussions has been third baseman Alex Bregman. Prior to his signing with the Boston Red Sox last spring, reports indicated the Cubs had offered him a four-year, $115 million deal that included opt-outs. While Bregman ultimately chose Boston, the Cubs remain in the mix, possibly hoping to revisit negotiations if the market’s dynamics shift.
The team’s interest in Bregman makes sense on multiple levels. On the surface, he’s an established hitter with a reputation for clutch performance. Off the field, his leadership qualities provide value to the clubhouse. Strategically, he fits into the Cubs’ roster plan since rookie Matt Shaw is still establishing himself at third base, and Nico Hoerner, who currently mans second, might be heading into free agency after 2026. Having a flexible and experienced third baseman like Bregman would stabilize a key position, whether as a starter or in a trade scenario. The Cubs have also been monitoring the markets for other potential infield upgrades, including Toronto’s Bo Bichette and outfielder Cody Bellinger, though each brings different considerations regarding fit and team chemistry.
Bregman’s market remains competitive, with other teams like the Detroit Tigers and Arizona Diamondbacks reportedly interested. Toronto, for instance, recently secured Kazuma Okamoto, a Japanese corner infielder, which could impact Bregman’s prospects of signing there. Still, Chicago’s front office appears to be in no rush, potentially waiting for softer market signals before making a decisive move.
Trade Scenarios and roster considerations
While free agency offers some options, the Cubs have also been exploring trade avenues to strengthen their offense. Given the roster construction, Bellinger would be an ideal fit in right field only if the team is willing to consider trades to create space. Seiya Suzuki and top prospect Owen Caissie are also options for corner outfield roles, meaning Bellinger’s signing could trigger roster reshuffling.
Similarly, if Bichette is pursued, his ideal position would likely be second base, where there could be a logjam if Hoerner remains in the mix. This suggests the Cubs might look to trade prospects or even young players in exchange for a controllable impact bat. The trade market remains an option for Chicago, especially as they evaluate whether to add hitters or prioritize pitching upgrades first.
Bolstering the Starting Rotation
Challenges in Securing a Top-tier Starter
Adding an elite starting pitcher remains a significant challenge for the Cubs. The recent signing of Japanese right-hander Tatsuya Imai by the Houston Astros for roughly three years and $63 million illustrates how competitive the market has become. The Cubs were among the interested teams but appeared hesitant to commit to such a lengthy and lucrative deal, reflecting the financial considerations at play.
Their current rotation includes Matthew Boyd, Cade Horton, Imanaga, and Jameson Taillon. Depth options like Javier Assad, Ben Brown, Rea, and Jordan Wicks provide additional flexibility, while Justin Steele continues his recovery from left elbow surgery, with a potential return in the first half of the season. The emergence of prospects such as Jaxon Wiggins is also on the Cubs’ radar, although they lack a clear ace at this point.
The question remains whether Chicago can afford to sign a premium starting pitcher while also adding a significant impact hitter. Currently, they have roughly $40 million available before reaching the first level of the Competitive Balance Tax threshold of $244 million. With two arbitration-eligible players—Assad and Steele—yet to be signed, the team’s flexibility could be limited unless they explore creative solutions.
Trade Market and Financial Flexibility
To accomplish both goals—adding a frontline starter and a significant hitter—the Cubs might need to explore the trade market. For example, the Marlins’ Edward Cabrera, a right-handed pitcher with three years of arbitration control, could be an intriguing target. Going this route might require trading away some prospects or even young positional players like Shaw, Caissie, or Moisés Ballesteros, which the team was reluctant to do during the last trade deadline.
The decision to pursue trades over free agency reflects the team’s desire to balance long-term flexibility with immediate competitiveness. Moving prospects or emerging players could allow Chicago to secure a proven arm without overextending their budget.
Conclusion
As the Cubs approach the 2026 season, their front office remains active but measured in their offseason strategy. The team continues to seek impactful additions at both the plate and mound, weighing the benefits and risks of free agency versus trade acquisitions. While several options are on the table—be it re-signing Bregman, acquiring Bichette through a trade, or snagging a top starting pitcher—they have yet to make their definitive move. The upcoming Cubs Convention and the months ahead will be critical in shaping the roster for what figures to be a pivotal year in their ongoing pursuit of sustained success.
