Former Cubs executive is set up to play spoiler in the Alex Bregman sweepstakes

A hush has largely settled over the sport in recent days, but that won't last long, especially with multiple signing deadlines looming, the biggest being Japanese right-hander Tatsuya Imai, who has until Jan. 2 to sign with an MLB team. The Chicago Cubs are among a handful of teams that have been connected to him of late.

Once Imai comes off the board, the rest of the starting pitching market will likely start to move - and the Cubs figure to be active there, one way or another. But the most persistent rumors of the winter continue to connect Chicago to Alex Bregman, who opted out of his deal with the Boston Red Sox at the end of the 2025 season in pursuit of big money.

The Cubs had a ton of interest in Bregman last offseason, but their final offer fell well short of Boston's three-year, $120 million pact that included opt-outs after the first two seasons. But if you think his opting out precludes him from playing for the Red Sox in 2026, you're sadly mistaken.

Red Sox could ruin Cubs fans' hopes of an Alex Bregman signing

Over at The Athletic (subscription required), Ken Rosenthal lays out the work turned in by Craig Breslow, chief baseball officer for the Red Sox, and how it's set Boston up to go big in free agency - calling a reunion with Bregman 'the best fit' among all the possible additions.

Breslow began his post-playing career in the Cubs' front office, working alongside Theo Epstein and Jed Hoyer from 2019-2023, establishing a reputation as a rising star in the league. Boston tapped him as Chaim Bloom's successor in Oct. 2023 and he's been reshaping the organization ever since - with no move as big as sending Rafael Devers to the Giants last summer and freeing up hundreds of millions of dollars in the process.

That newfound financial flexibility gives Breslow all kinds of paths forward as he looks to keep adding this offseason, even after acquiring Willson Contreras and Sonny Gray from the Cardinals. Bregman checks all the boxes, but Rosenthal notes the Red Sox could look elsewhere to names like Bo Bichette or Ketel Marte if they miss out on the veteran All-Star.

Bregman would give the Cubs a proven presence at third and immediately offset the loss of Kyle Tucker - but they're not going to land him playing it safe and refusing to get uncomfortable financially. With Boston, Toronto and others lurking, competition for the two-time World Series champion could soon start heating up.