The Chicago Cubs have Alex Bregman. Alex Bregman has $175 million. What do the Boston Red Sox have? There’s a mountain of regrets, a huge void in leadership, and a lot of explaining to do.
Bleacher Nation’s Michael Cerami first reported Bregman’s $175 million deal with the Cubs, which spans five years and includes $70 million worth of deferred funds. Notably, it includes a full no-deal provision but does not include an opt-out provision. That means Bregman, who turns 32 in March, will be a member of the Cubs for at least the next five years.
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It’s a significant investment for a player that age, especially one with frequent lower-body issues, but Bregman’s consistent offensive prowess, reliable third base glove and heartwarming clubhouse profile elevated the Cubs into legitimate World Series contenders. He’s made Chicago a better baseball team moving forward; let’s leave the “value” gripes another day.
For the Red Sox, the result was nothing short of a complete disaster. The Red Sox signed the long-term Houston Astros last winter to a short-term deal filled with opt-outs. Bregman’s exit from Fenway Park marked the most embarrassing culmination of a most tumultuous year. Boston’s shocking decision to trade away franchise cornerstone Rafael Devers in June was directly related to Bregman’s presence at the hot corner.
Alex Bregman’s tenure with the Red Sox was short-lived, as negotiations over a no-trade clause seemed to prompt him to seek work elsewhere. (Photo by Daniel Shirey/MLB Photo via Getty Images)
(Daniel Shire via Getty Images)
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If team owner John Henry and chief baseball officer Craig Breslow are committed to Bregman long-term, offloading Devers would make some sense. Bregman had great success in his one season at Fenway, although he only lasted two months there. Before the injury, he was performing like a top-10 MVP candidate. A group of the club’s younger players continue to talk about Bregman’s leadership qualities. His consistency helped Boston overcome a drama-filled season and reach the playoffs, where the team was one win away from defeating the Yankees.
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None of that matters now. The Red Sox were steadfastly loyal to reason and didn’t want to spend money. They left behind a group of angry fans who were confused that neither Devers nor Bregman was around. Breslow tried to appease the Red Sox faithful in an email Q&A with Mass Live’s Chris Cotillo on Sunday, but the executive’s jargon-filled, carefully crafted answers only reinforced criticism that he runs the club with a cold, mechanical, dehumanizing efficiency.
But even the optimistic, long-term Breslow admits the outcome of the Bregman-Devers saga was less than ideal.
He typed to Cotillo: “Both outcomes we face now are ideal, but both will be evaluated over a longer period of time.”
The rest of the interview was mostly empty general manager talk, but there were some unintentionally honest moments that heightened concerns about Breslow’s approach to business. As for why Bregman chose Chicago, a Boston baseball team executive said: “It would be foolish and unfair for me to guess what was most important in their decision.”
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One might argue that instead of “Stupid and unfair” It is prudent and necessary to understand the factors that influenced Bregman’s “decisions.” For example, an unwillingness to include a no-trade clause in his contract appears to be a major sticking point for Bregman and his agent, Scott Boras. Bregman wants stability after two consecutive winters of tumultuous waters in free agency. He wanted a place where his family could put down roots, buy a home and be part of a community, just like he had in Houston. Everyone in New England knows this.
Bregman’s desire for a no-trade clause makes more sense given the shadow of Devers’ departure seven months ago. If the Red Sox were willing to change course and send a guy like Devers out of town, why would they hesitate to do the same with Bregman? Via other reports from Mass Live, the team pointed to their “organizational policy” in refusing to grant Bregman a trade ban. But in the end, this computational inflexibility proved to be a miscalculation.
The whole thing is a lesson in public relations disaster, a textbook example of how not to engage with your fan base. It’s unclear whether the Red Sox don’t know this or simply don’t care. The majesty of Fenway Park (and surrounding real estate assets) ensures that teams will print money regardless of the success of the on-field product. This is Fenway Sports Group’s shrewd approach to operations. It’s also cruel, insulting and short-sighted.
Ultimately, if the team wins, everything will be fine. The 2026 Red Sox are still a talented team. Garrett Crochet is one of the top four pitchers on the planet. Roman Anthony is a volcano of talent. The additions of Sonny Gray and Wilson Contreras have legitimate impact. Positionally, the roster is a jigsaw puzzle of borderline pieces, a disjointed collection of quality players that a trade or two could help simplify.
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Still, Boston was able to overcome that momentum, win 95 games and make a strong comeback in October. If that happens, fans will fully support Fenway and Breslow’s commitment to the process. As always, success heals everything.
But with Bregman gone, it’s hard to argue that the Red Sox are better now than they were just a few months ago, when their season ended with disappointment in the pinstripes. This is a reality that could have been avoided, whether it was more millions of people or more human conversations.
Either way, the outcome is the same: Red Sox leadership looks bad and has a long to-do list that includes explaining to angry fans how this happened.
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