CHICAGO – During the Winter Meetings last month, Cubs president of baseball operations Jed Hoyer expressed that there was a “real focus” and “energy” to the team’s pursuits on multiple fronts. He was also quick to add a cautionary qualifying statement.
“I think it’ll lead to activity – I can’t tell you when,” Hoyer said. “We could have an active December. We could have an active January. I don’t know. We’re not going to do bad deals just to do something quick.”
Nearly a month later, with 2026 upon us and Cubs Convention (Jan. 16-18) approaching, Hoyer and his front-office team have yet to make a big-ticket splash this offseason. There has been nearly $30 million spent between the bullpen and bench, plus Shota Imanaga’s decision to stay for $22.025 million via the qualifying offer, but two primary goals remain unsolved: adding an impact bat and/or a starting pitcher.
Let’s look at the options remaining for the North Siders in those areas:
The rotation was viewed as the top priority going into the offseason, but Imanaga’s decision to stay, the re-signing of swing-man Colin Rea and the potential in-season return of Justin Steele from injury helps the depth on that front. That at least helps the Cubs be more open-minded about bringing in an experienced bat.
That is where the steady stream of reports linking the Cubs to free-agent third baseman Alex Bregman come into play, along with some recent buzz about Chicago keeping tabs on the markets for infielder Bo Bichette and outfielder Cody Bellinger. Given the roster construction, Bregman is the most logical fit.
Before Bregman signed with the Red Sox last spring, there were reports that the Cubs offered him a four-year, $115 million deal that included opt-outs. The North Siders are again lingering in this race – likely hoping to see if the desire for a lengthy deal loosens a bit. Boston is still in the mix, with the Tigers and D-backs sprinkled in in rumors. The Blue Jays were also viewed as a fit, but Toronto just reeled in Japanese star corner infielder Kazuma Okamoto.
Bregman fits not only for his skill on the field and reputation in the clubhouse, but 2025 rookie Matt Shaw is still establishing himself at third base and second baseman Nico Hoerner might hit free agency after ‘26. Shaw or Hoerner could be trade candidates, or Shaw could shift into a super-sub role, helping create a contingency plan for second base if Hoerner is not extended.
Bellinger only makes sense for right field if the Cubs plan on loosening up the roster via trade, given that Seiya Suzuki and top prospect Owen Caissie are in the plans for that position. Similarly, even if Bichette were willing to move off shortstop, there is a logjam if the desired landing spot for him is second base. That said, Chicago is surely looking at trade scenarios as a possible way to add to its rotation.
2) Adding an impact starting pitcher
The options are dwindling on this front, especially after Japanese right-hander Tatsuya Imai’s recent decision to sign with the Astros. The Cubs were looking into the righty, but Imai’s contract (reported to be three years and $63 million guaranteed) shows that Chicago was likely not the only club hesitant to dish out a lucrative, long-term offer.
Right now, the Cubs’ rotation features: Matthew Boyd, Cade Horton, Imanaga and Jameson Taillon. Javier Assad, Ben Brown, Rea and Jordan Wicks offer depth options for the rotation or bullpen. Steele is working his way back from a left elbow injury and could return in the first half. Prospect Jaxon Wiggins is on the big league radar.
One unanswered question is whether Chicago could afford to add a bat like Bregman and also sign a free-agent starter, or if this is a one-or-the-other situation. There are still two unsigned arbitration-eligible players (Assad and Steele) to factor into the budget, and a little under $40 million projected to be available before running into the first Competitive Balance Tax threshold ($244 million).
Chicago could perhaps thread the needle and solve both goals by exploring the trade market (Marlins righty Edward Cabrera comes with three years of control via arbitration, for example). That would hypothetically require being more open-minded to trading away a young player such as Shaw, Caissie or catcher Moisés Ballesteros. The Cubs were unwilling to do that at the Trade Deadline last summer, when they looked into impact arms on the market.
