Kyle Schwarber re-upping with the Philadelphia Phillies was probably the first domino to fall ahead of Alex Bregman resolving his own free agency. The Boston Red Sox were among the teams involved in Schwarber's sweepstakes, and Boston's desire to explore non-Bregman possibilities could be the key to the Cubs landing the All-Star third baseman.
Whether it was Schwarber, Bo Bichette, or a potential trade for Ketel Marte, the Red Sox are eyeing potential alternatives in the event that they aren't able to bring back Bregman this offseason. Along those lines, The Athletic's Sahadev Sharma joined Foul Territory and outlined the reason why the Red Sox moving on from Bregman is the key to the Cubs' pursuit.
As expected, Sharma points out that the Cubs likely won't position themselves to outbid Boston for Bregman, but if the Red Sox either sign Bichette or trade for Marte, that would effectively rule out a reunion with the veteran infielder. Leaving the Cubs and Tigers as the top teams in his market, a scenario where Chicago would certainly offer more than Detroit.
It would appear the Cubs are waiting for the Red Sox to acquire another bat who isn't Alex Bregman before pursuing him, says @SahadevSharma. pic.twitter.com/QVpEfTikoi
— Foul Territory (@FoulTerritoryTV) December 9, 2025
There's really only one scenario where the Chicago Cubs come away from this offseason with Alex Bregman.
It's worth pointing out that when it was the same three teams chasing Bregman last offseason, the Tigers did, in fact, top the Cubs' offer. With the Cubs maintaining their belief in Matt Shaw, it likely isn't a foregone conclusion that they would outbid the Tigers this time around.
It would also be fair to assume that the Cubs' pursuit of a top-of-the-rotation arm will be tied to whether or not they can land Bregman this offseason. If the Cubs are the top bidder for Tatsuya Imai in the coming weeks, that likely will end a pursuit of Bregman, who could be seeking an AAV of at least $30 million.
However, if Zac Gallen, Michael King, or trading for a cost-controlled ace is the move for the Cubs' rotation, it would seem likely that Jed Hoyer and Co. would be given the green light to pursue Bregman.
The Cubs adding Bregman this offseason shouldn't be viewed as likely, but circumstances could change the outlook very quickly. It's the reason why the Cubs are remaining in touch with Scott Boras, just in case the stars align in their direction.
