Inside The Red Sox

Red Sox's Alex Bregman Tactics Look Worse As New Evidence Emerges

What were the Sox doing here?
Jackson Roberts|
Sep 5, 2025; Phoenix, Arizona, USA; Boston Red Sox third base Alex Bregman (2) mkaes the off balance throw for an out against the Arizona Diamondbacks in the first inning at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images
Sep 5, 2025; Phoenix, Arizona, USA; Boston Red Sox third base Alex Bregman (2) mkaes the off balance throw for an out against the Arizona Diamondbacks in the first inning at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images | Rick Scuteri-Imagn Images

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Boston Red Sox

The Boston Red Sox are having a brutal couple of days, and the more we learn about their ill-fated pursuit of Alex Bregman, the worse they look in the eyes of the public.

Knives have been out since Bregman reportedly agreed to a five-year, $175 million deal with the Chicago Cubs on Saturday night. On Sunday, MassLive reported that Boston had offered $165 million, but refused to grant Bregman the no-trade clause he got from Chicago, and also wanted to pay him significantly delayed deferrals.

On Monday, A.J. Pierzynski of "Foul Territory" dropped an alleged timeline of how the events played out, and if everything he said was 100% accurate, the Red Sox should be hanging their heads in shame over the way they treated yet another franchise star.

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Pierzynski goes in on Red Sox for Bregman handling

"They made an offer early in the offseason," Pierzynski claimed. "And it made Alex a little bit mad, and they would not move. So then the Red Sox were like, 'Okay, well take it or leave it.' They would not budge.

"Then, Bregman's camp goes back to them with Boras and says, 'Hey, we have a higher offer, and we're going to probably take it.'"

From there, Pierzynski asserted that the Red Sox didn't get to the offer for $165 million until Bregman's camp had essentially told them that they were going to accept a different offer. Even then, the bigger Boston's offer got, the more money they were looking to defer.

"So Bregman's like, 'I'm getting more money, in a shorter amount of time, I'm going to the Cubs,'" Pierzynski concluded. "The Red Sox would not move, and really wouldn't negotiate ... until it was too late."

It's one source of evidence to be used against the Red Sox, and perhaps people in Boston's camp would dispute some of the events happening as Pierzynski says they did. But at the very least, it seems safe to assert that the Red Sox did some things throughout the process that soured Bregman on the idea of coming back.

Pierzynski didn't even mention the lack of a no-trade clause, which seems like an indefensible organizational policy. The Red Sox have a credibility problem that they'll have to solve before future free agents will choose them.

More MLB: Red Sox-Bo Bichette Update Drops As Boston Seeks Alex Bregman Pivot

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org

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