How Red Sox botched negotiations with Alex Bregman: ‘A little crazy’

How Red Sox botched negotiations with Alex Bregman: ‘A little crazy’

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The Red Sox lost a game of chicken.

Boston lost star third baseman Alex Bregman to the Cubs, in part because they made him a little “crazy” while taking a hard line in negotiations and ultimately didn’t really believe he had a better offer available, according to former Boston catcher and “Foul Territory” host AJ Pierzynski.

Bregman signed a five-year, $175 million deal with the North Siders, while the Red Sox reportedly forked out $165 million over five years. per Mass Live.

“The Red Sox literally wouldn’t move, wouldn’t budge and really wouldn’t negotiate until it was too late,” Pierzynski said this on Monday.

Boston signed Bregman to a three-year, $120 million deal last offseason, which included an opt-out after the first year, and the 31-year-old exercised that clause after posting an .821 OPS last season.

Pierzynski claimed that Boston made an early offer, to which Bregman’s camp — he is represented by super agent Scott Boras — responded that the market for infielders was “higher.”

This did not sit well with the two-time World Series champion.

“It made Alex a little angry that they wouldn’t move,” Pierzynski said. “So then the Red Sox said, ‘OK, take it or leave it.’ They won’t give in.”


New Cubs third baseman Alex Bregman wears a Blackhawks jersey during their game against the Oilers in Chicago on January 12, 2026. Kamil Krzaczynski-Imagn images

Bregman’s camp later reportedly told the Red Sox that they had made a higher offer and were likely to accept that deal, and Pierzynski claimed that Boston – led by head baseball agency Craig Breslow – told the three-time All-Star that they didn’t believe him and that if he really had it on the table, he should take that offer.

When Bregman made it clear that he indeed had such a deal, Boston ultimately increased its offer to $165 million over five years.

However, that offer was subject to a “significant” delay, according to Mass Live.


Red Sox Chief Baseball Officer Craig Breslow and President & CEO Sam Kennedy during a press conference.
Red Sox chief baseball officer Craig Breslow. AP

Bregman decided to take the bigger deal that averages $35 million per season.

“Bregman was already one, crazy, and two, had a higher offer and the more they tried to drag it out, the longer and further the delay became,” Pierzynski said. “So Bregman says, ‘I’ll get more money in a shorter amount of time, I’ll go to the Cubs.’

His defection likely leaves Boston one bat short this season in what has been a puzzling offseason for the franchise.

Looking for a No. 2 starter to complement Garrett Crochet in the rotation, the Sox added veteran Sonny Gray and intriguing ex-Pirates starter Johan Oviedo while not re-signing Lucas Giolito, who remains a free agent.

Boston acquired Willson Contreras to play first base, but has now lost Bregman.

You can argue that Boston is a better team, but the question is how much has it improved.

The Blue Jays have made marked improvements after winning the AL East and advancing to Game 7 of the World Series, while the Orioles have also upgraded their roster.

The Yankees have taken a step back as of now as there is no replacement for Cody Bellinger on the roster if he moves on.


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