The Chicago Cubs entered the offseason with two clear needs: replace Kyle Tucker's production and add a front-of-the-rotation starter. With spring training six weeks away, they've accomplished neither while watching competitors snatch up talent around them.
Tatsuya Imai signed with Houston. Kazuma Okamoto went to Toronto. Dylan Cease landed a seven-year deal in Canada. Pete Alonso joined Baltimore. The market that once seemed full of possibilities has shrunk to a handful of expensive options and question marks.
President of baseball operations Jed Hoyer has spent nearly $30 million rebuilding the bullpen and brought back Shota Imanaga on a qualifying offer, but the Cubs remain fundamentally the same team that lost to San Diego in the Wild Card round—only now without Tucker's bat in the middle of the order.
The Bregman Dilemma
Alex Bregman has been connected to the Cubs throughout the winter, but Chicago appears to be operating on the periphery rather than leading the chase. Reports suggest the Red Sox, Blue Jays, and Diamondbacks are more aggressive suitors, with Boston recently making what's described as an "aggressive" offer to retain him.
The financial reality is challenging. The Cubs have roughly $38 million to spend before hitting the luxury tax threshold. If Bregman's market settles around five years and $160 million—as some recent reports suggest—that would eat up most of Chicago's remaining flexibility and leave little room to address the rotation.
Last offseason, the Cubs reportedly offered Bregman four years and $115 million. Asking them to jump to $160 million for a player who turns 32 in March would represent a significant departure from their recent spending patterns. Only Dansby Swanson's seven-year, $177 million deal exceeds that threshold in the Hoyer era.
Pitching Options Narrow
With Imai off the board, the Cubs face a thinner starting pitching market. Framber Valdez, Ranger Suarez, and Zac Gallen remain available, but all three figure to command significant multi-year commitments.
Gallen has emerged as a frequently mentioned target. The right-hander posted a 3.70 ERA over 24 starts last season and would slide comfortably into the middle of Chicago's rotation. Suarez presents an intriguing option given his success at Wrigley Field—a 1.88 ERA with zero home runs allowed in 14.1 career innings there—and proven postseason track record.
The question is whether the Cubs will commit to any of them at the prices they're likely to command. Hoyer's approach this winter has been measured, focusing on value and avoiding overpays. That discipline may have served the organization well in some instances, but it's also left them watching others act while they deliberate.
The Bo Bichette Wild Card
A new name has entered the conversation: Bo Bichette. Reports indicate the Cubs are among several teams that have "checked on" the Blue Jays shortstop, who could be available via trade.
Bichette presents an interesting fit. At 27 years old, he'd bring a right-handed bat to balance the lineup and could play third base this season before potentially shifting to second when Nico Hoerner hits free agency after 2026. His steep swing plane and unique approach make him a polarizing player, but there's upside if he rebounds from a disappointing 2025 campaign.
The catch is what it would cost. Acquiring Bichette would require both prospects and taking on his salary, then signing him to an extension. It's the kind of complicated, multi-layered transaction that requires conviction—something the Cubs haven't shown much of this winter.
Budget Constraints and Reality
The Cubs' payroll currently sits around $194 million with a luxury tax number near $209 million. They have room to add, but not enough to make multiple splashes without exceeding the threshold for the first time in years.
This creates a difficult choice: commit to Bregman and hope to find pitching through trades, or prioritize rotation help and bank on Matt Shaw and internal options to fill the offensive void. The Cubs appear reluctant to go all-in on either path.
Chicago also still needs to finalize arbitration figures with Javier Assad and Justin Steele, further limiting their flexibility.
The Convention Clock
Cubs Convention begins January 16, giving Hoyer less than two weeks to make a significant move before facing season-ticket holders and die-hard fans. Last year's convention came shortly after the Tucker trade was announced, providing something concrete to discuss and generate excitement.
This year feels different. There's no blockbuster trade to trumpet. The bullpen additions are solid but uninspiring. The big questions remain unanswered.
Hoyer's message has been consistent: the Cubs are looking for the right value at the right time. That's reasonable in theory. In practice, it means watching Dylan Cease get seven years from Toronto, seeing the Astros land Imai, and having the Blue Jays add Okamoto while Chicago continues to evaluate.
What Remains
The good news—if you can call it that—is that impact players are still available. Bregman could still land in Chicago if the price drops or the Cubs change their approach. Valdez, Suarez, and Gallen are all talented pitchers who would improve the rotation. Tucker technically remains unsigned, though a reunion seems highly unlikely given how last season ended.
There's also the trade market. Names like Zac Gallen (if the Diamondbacks pivot) or mid-tier arms could become available as teams make their own decisions. The Cubs have prospects to deal, even if the farm system isn't as deep as it once was.
But the clock is ticking. Spring training pitchers and catchers report in six weeks. Every day that passes without action is another day the roster remains fundamentally incomplete.
The Risk of Standing Still
This Cubs team finished 83-79 last season and got swept in the Wild Card round. They lost Tucker and haven't replaced him. Justin Steele is recovering from Tommy John surgery and his return timeline is uncertain. The rotation depth has questions beyond the top three.
The organization is close to contention—close enough that one or two smart additions could vault them into legitimate playoff contention. But close doesn't win anything, and the gap between the Cubs and teams like the Dodgers, Phillies, and Mets continues to widen as those franchises spend aggressively while Chicago exercises caution.
Hoyer has earned credibility with his methodical approach. The infrastructure is solid. The development pipeline has produced results. But there comes a point where being smart about spending bleeds into being too conservative, where avoiding bad contracts means missing opportunities to capitalize on a competitive window.
If the Cubs finish this offseason with only bullpen additions and no significant help in the rotation or lineup, it will be hard to view the winter as anything but a failure—regardless of how reasonable the individual decisions might have been.
The options are dwindling. The competition is getting stronger. And Cubs fans are left wondering if their front office will act before it's too late.