Red Sox Embarrassed Again As Details Emerge On Alex Bregman Negotiations

Mistake after mistake after mistake...

Jan 12, 2026; Chicago, Illinois, USA; Chicago Cubs third baseman Alex Bregman watches an NHL game between the Chicago Blackhawks and Edmonton Oilers during the third period at United Center. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

At this point, it's impossible not to call the Alex Bregman situation one giant screw-up for the Boston Red Sox.

The more we learn about how the Red Sox conducted themselves in pursuing Bregman, the more we have to reconcile the fact that Bregman wanted to be in Boston until the team pushed him away. And to do so while they were still actively making him offers is almost impressive.

A Wednesday report from Alex Speier of The Boston Globe had further revelations on just how embarrassing Boston's behavior was toward the latter stages of the negotiations.

If you like our content, choose Sports Illustrated as a preferred source on Google.

How Red Sox cost themselves Bregman

According to Speier, the Red Sox held firm at their final offer of $165 million for long enough that Bregman's camp, angry at the team's behavior, didn't give Boston a chance to match the Cubs' final offer of $175 million.

"The Sox felt confident in their five-year, $165 million offer, but internally, wanted to avoid bidding against themselves rather than upping their bid at the start of the year in an effort to close out a deal," Speier wrote.

"It turned out the Sox would have been bidding not against themselves but the field. And once again, the field won, this time with the Cubs ... racing past the Sox with their five-year, $175 million offer that included both fewer deferrals than the Sox and a full no-trade clause. (Per industry sources, the agreement with the Cubs was presented to the Sox as a fait accompli, without a chance to counter.)"

We've discussed it here ad nauseam, but it still truly makes no sense that the Red Sox weren't willing to offer Bregman a no-trade clause. They traded Rafael Devers just seven months prior, presumably because Bregman was something resembling a perfect anti-Devers in the clubhouse, but weren't willing to guarantee the latter they wouldn't treat him like the former.

To bungle the negotiations to the point where a player who wanted to be in Boston, in Speier's terms, wouldn't even let them try at the end to bridge a $10 million gap? Shameful.

More MLB: Red Sox-Bo Bichette Update Drops After Phillies Meeting