How Red Sox botched Alex Bregman negotiations: ‘A little bit mad’


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 “mad” while drawing a hard line in negotiations and ultimately did not truly believe he had a better offer available, according to former Boston catcher and “Foul Territory” host A.J. Pierzynski.

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

“The Red Sox literally would not move and would not budge and really not negotiate until it was too late,” Pierzynski said Monday.

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

Pierzynski alleged that Boston made an offer early to which Bregman’s camp — he’s repped by super agent Scott Boras — countered that the infielder’s market was “higher.”

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

“It made Alex a little bit mad they would not move,” Pierzynski said. “So then the Red Sox were like, ‘OK, take it or leave it.’ They will not budge.”


Alex Bregman watching an NHL game between the Chicago Blackhawks and Edmonton Oilers.
New Cubs third baseman Alex Bregman wears a Blackhawks jersey during their game against the Oilers in Chicago on Jan. 12, 2026. Kamil Krzaczynski-Imagn Images

Bregman’s camp allegedly later told the Red Sox they had a higher offer and would probably accept that deal, and Pierzynski claimed that Boston — led by chief baseball office Craig Breslow — told the three-time All-Star they did not believe him and he should take said proposal if he truly had that on the table.

When Bregman made it clear that he did indeed have such a deal, Boston eventually upped its offer to $165 million over five years.

However, that offer had “significant” deferrals, per Mass Live.


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

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

“Bregman was already one, mad, and two, had a higher offer and the more they tried to stretch it out, the longer and further down the road the deferrals got,” Pierzynski said. “So Bregman’s like, ‘I’m getting more money in a shorter amount of time, I’m going to the Cubs.”

His defection leaves Boston probably one bat short this offseason in what has been a puzzling offseason by the franchise.

The Sox sought a No. 2 starter to complement Garrett Crochet in the rotation and 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 man first base, but now has lost Bregman.

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

The Blue Jays have made clear 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, as of now, have taken a step back since there is no Cody Bellinger replacement on the roster should he move on.




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