The most important week in MLB’s offseason is occurring next week during the annual winter meetings. This is when the hot stove really picks up steam, and many of the top free agents will likely find their future homes.
This is also a time with a lot of trade activity, given that baseball’s front office executives are all under the same roof.
Therefore, Chicago Cubs fans should expect some activity in the weeks to come. And given some of the recent reports that have surfaced, there seem to be a few key free agents that could end up at Wrigley Field by Opening Day 2026.
Here are the latest Cubs stories to catch up on as the winter meetings approach.
Cubs news and notes
Cubs Linked to Alex Bregman (once again) – On December 4, New York Post MLB insider Jon Heyman noted that the Cubs are one of several teams that are showing interest in free agent third baseman Alex Bregman.
This is not the first time Chicago has been in pursuit of Bregman, as they offered him a lucrative contract when he was a free agent last offseason before he ultimately signed with the Boston Red Sox. Acquiring Bregman would be one of the best ways for the Cubs’ front office to replace Kyle Tucker’s production in the lineup, given that Tucker is expected to sign with another club.
Sep 25, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman | John E. Sokolowski-Imagn Images
What A Cubs Bregman Pursuit Means for Matt Shaw – If Chicago were to bring Bregman on board, it would mean that incumbent third baseman Matt Shaw would not have a starting spot. Jon Heyman alluded to this in a recent live stream by questioning what Shaw’s future in Chicago would look like if the team signed Bregman.
While Shaw played well down the stretch last season, he didn’t do enough to secure a starting job and convince the organization that he deserves to be the Cubs’ third baseman of the future. 2026 will be pivotal for Shaw, as he looks to prove that the team doesn’t need to seek an upgrade at the hot corner.
Zac Gallen’s Unique Cubs Connection Could Spark Free Agency Move – It must have been a wild day for Zac Gallen, as news broke during the morning of December 6 that he had signed with the Cubs. However, this news was quickly disputed by MLB insiders, with ESPN’s Jeff Passan tweeting definitively, “Zac Gallen does not have a deal and is not close to finalizing one.”
Zac Gallen | Joe Camporeale-Imagn Images
That said, Gallen does have a clear reason why he may want to sign with the team. Gallen’s best years with the Diamondbacks were 2020, 2022, and 2023, with the common denominator amongst them being that he was throwing to the same catcher: Carson Kelly. With Kelly now a Cub, Gallen may be hoping to strike lightning once more should the duo pair up again.
Cubs Linked to Tatsuya Imai and Michael King – Perhaps the biggest reason why Chicago wouldn’t make a true push for Bregman is that their interest is more in acquiring a frontline starting pitcher, as that’s their more pressing need this offseason.
There are five free agent starting pitchers who could be considered ace-caliber enough for the Cubs right now. Among these, Chicago has been directly linked to former Padres pitcher Michael King and Japanese hurler Tatsuya Imai. While the Cubs could be in play for any of the top free agent arms, it seems that Imai and King are the front office’s two preferred pitchers at this point.
The Cubs will be a “strong player” for NPB star Tatsuya Imai (@MLBBruceLevine).
2025 NPB Stats:
163.2 IP | 1.92 ERA
27.8 K% | 7.0 BB%
Imai could fix a lot of problems for the Cubs, but they will need to go way out of their comfort zone to land him.pic.twitter.com/X9LADYZlDz
— The Wrigley Wire (@TheWrigleyWire) December 4, 2025
Cubs’ Free Agency Budget Revealed – The reason Chicago likely can’t sign Bregman, a frontline starting pitcher, and retool their depleted bullpen is that they simply aren’t willing to spend that sort of money.
But that’s not to say this team isn’t willing to drop some serious money this offseason, which Cubs insider Bruce Levine revealed by saying there is, “upwards of $50 to $60 million yet to be spent on this year’s payroll” for the Cubs on a December 4 episode of 670 The Score’s Mully & Haugh Show.
He expects them to spend around $50 million, which would surely be enough to sign a top hitter or pitcher, along with adding several key relief pieces, and perhaps enough for more.
The Cubs have $50 million to $60 million more to add to their 2026 payroll, @MLBBruceLevine‘s sources told him.
“There’s that flexibility in there,” he says. pic.twitter.com/lbEIVJwpZP
— 670 The Score (@670TheScore) December 4, 2025
Key Stat Reveals Why Ranger Suarez Could Thrive With The Cubs – Joel Reuter of Bleacher Report played matchmaker for MLB’s top free agents and paired Ranger Suarez with the Cubs. His reasoning? Suarez is a great groundball pitcher, and the Cubs have the defense to take advantage of it.
“Ranger Suárez has been a groundball pitcher throughout his career, with a strong 52.0 percent groundball rate for his career, and that means a team with a strong defensive infield might be his ideal landing spot,” Reuter noted.
Matthew Boyd Reflects on NLDS Performance, World Baseball Classic News – Cubs pitcher Matthew Boyd recently did an interview with Foul Territory and addressed his NLDS Game 1 outing, where he was pulled after 0.2 innings and four runs conceded against the Milwaukee Brewers, which led to a tough defeat.
“It is unfortunate that happened on short rest, because it is easy to point to that…but, physically, mentally, I felt great. The Brewers just got me. We made a new game plan for five days later and attacked that and it worked out in my favor,” Boyd said.
Matthew Boyd says his rough outing in Game 1 of the NLDS had nothing to do with short rest.
“They [the Brewers] just got me.” pic.twitter.com/7EBaEbvaCp
— Foul Territory (@FoulTerritoryTV) December 3, 2025
Boyd also announced that he’d be playing for Team USA in the 2026 World Baseball Classic, joining teammate Pete Crow-Armstrong.
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