The Chicago Cubs are back in the thick of the Alex Bregman conversation-and this time, the momentum might actually be tilting their way.
Coming out of the Winter Meetings, there’s a growing sense around the league that the Cubs are positioning themselves to make a serious run at the veteran third baseman. And while nothing is ever set in stone during MLB’s offseason chess match, the signs are starting to point toward Chicago being a legitimate landing spot for Bregman in 2026 and beyond.
One key development? The Boston Red Sox-long viewed as the Cubs’ primary competition for Bregman-may be cooling on the idea of a reunion.
Jared Carrabis, a plugged-in voice around Red Sox Nation, hinted that his optimism about Bregman returning to Boston is fading. He reminded fans how quickly things can change in free agency-referencing how Xander Bogaerts seemed destined to stay in Boston before the Padres stunned everyone with a massive offer-but admitted that the current vibe around Bregman doesn’t feel promising.
That shift in tone from Boston could open the door wider for the Cubs, who have both the financial flexibility and the positional fit to make a compelling pitch. Even with a conservative estimate, Chicago has roughly $30 million in payroll space to work with before Opening Day.
If they’re feeling bolder, that number could push closer to $40 million. That’s more than enough to put together a competitive offer for Bregman, especially if they’re willing to stretch to a fifth year.
And there’s reason to believe they might. While the Cubs have shown caution with long-term deals in recent years, they reportedly offered Bregman a four-year contract last offseason. With their books opening up significantly after 2026, an extra year could be the sweetener that gets a deal done.
Meanwhile, Boston appears to be pivoting. With Bregman possibly slipping out of reach, the Red Sox have been linked to other offensive reinforcements-most notably Ketel Marte of the Diamondbacks and catcher Willson Contreras in potential trade scenarios. That kind of activity suggests they’re preparing for a Plan B, rather than waiting around for Bregman to circle back.
It’s also worth noting that both the Cubs and Red Sox seem wary of handing out long-term mega-deals, a philosophy that Boston’s Chief Baseball Officer Craig Breslow may have picked up during his time under Cubs President Jed Hoyer. But Chicago’s situation is a little more flexible. If they want to push the envelope on Bregman, they have the payroll room-and arguably the motivation-to do it.
This isn’t the first time the Cubs have looked poised to land Bregman. Back in February, it felt like a deal was within reach before things fell apart. Now, that familiar feeling is creeping back in-only this time, there’s a bit more smoke behind the fire.
For Cubs fans, the idea of Bregman anchoring the infield and bringing his postseason pedigree to Wrigley is more than just a pipe dream. It’s a scenario that’s very much in play. And if Boston is indeed stepping back, Chicago might finally be ready to step forward.