The Chicago Cubs made a big splash this offseason when they seemingly came out of nowhere to sign three-time All-Star third baseman Alex Bregman.
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The 5-year, $175 million deal was a departure from standard Cubs operating procedure. It included deferred money, a previous no-no with team ownership. The deal also included a no-trade provision, which, as things would turn it, proved to be a big (and possibly deciding) factor for the former Gold Glover.
Wounded pride was part of Bregman decision
Jul 21, 2025; Philadelphia, Pennsylvania, USA; Boston Red Sox third base Alex Bregman (2) against the Philadelphia Phillies at Citizens Bank Park. Mandatory Credit: Eric Hartline-Imagn Images
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But there was, apparently, more to Bregman leaving Boston than a little more money (Boston offered a $165 million deal) and the no-trade clause. Pride reportedly played a big role in the veteran’s decision.
“It made Alex a little bit mad they would not move,” former major leaguer (and former Red Sox catcher) A.J. Pierzynski said on a January episode of his “Foul Territory” podcast. “So then the Red Sox were like, ‘OK, take it or leave it.’ They will not budge.”
“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 added. “So Bregman’s like, ‘I’m getting more money in a shorter amount of time, I’m going to the Cubs.”
Pierzynski’s account was supported by a recent report by MLB insider Bob Nightengale at USA Today.
“The Red Sox were confident they had the highest bid, and thought they’d (be) bidding against themselves,” Nightingale wrote. “So, basically, it was (a) take-it-or-leave-it offer.
“Bregman left it.”
Animosity towards Red Sox front office?
Aug 12, 2025; Houston, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) runs to first base on a single during the ninth inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images
A terse “If Alex Bregman wanted to be here, ultimately he’d be here” response by Red Sox president Sam Kennedy would pretty much be the only public comment about what many perceive as a costly offseason contract bungling.
Bregman has refused to speak publicly about the precise reason he chose to leave a team and a city he insists were tremendous and will always be a cherished part of his life.
“I just really don’t want to get into it,’’ Bregman told Nightengale. “It’s not worth it.”
But Bregman’s mature approach to what could’ve been an ugly and public war of words doesn’t necessarily mean that he wouldn’t take a subtle jab at his former team.
Bregman and Devers bond in social media post
Feb 22, 2026; Scottsdale, Arizona, USA; San Francisco Giants designated hitter Rafael Devers (16) reacts after missing a pitch against the Chicago Cubs in the third inning at Scottsdale Stadium. Mandatory Credit: Rick Scuteri-Imagn Images
A recent collage of spring training photos on his verified Instagram account spotlights one particular pic that could be construed as a dig at the Boston front office.
In it, he shows himself happily shaking hands with former Red Sox third baseman Rafael Devers, under the caption “Baseball Time.”
Devers, of course, had a very ugly and public falling out with the Boston front office last year after he was moved from third base to accommodate Bregman and asked to play a first base/DH role. The bickering was so nasty that the team traded him to the San Francisco Giants in mid-June.
Bregman showcasing two seemingly disgruntled (or, at the very least, frustrated) former Red Sox stars bonding as happy members of different organizations is probably not a coincidence.
For a guy like Bregman, who is universally regarded as one of the true good guys in the sport, this is about as close to a scathing mic-drop burn as you’re likely to get.
The 31-year-old third baseman will now move on to play for Team USA in the World Baseball Classic, alongside new teammates Pete Crow-Armstrong and Matthew Boyd, before heading into the 2026 season as a Cub.
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