The Chicago Cubs have Alex Bregman. Alex Bregman has 175 million bucks. And what do the Boston Red Sox have? A mountain of regret, a gargantuan leadership void and a whole lot of explaining to do.
Bregman’s $175 million deal with the Cubs, first reported by Michael Cerami of Bleacher Nation, will run for five years and features $70 million worth of deferred money. Notably, it includes a full no-trade clause but not opt-outs. That means Bregman, 32 years old in March, will be a Cub for at least the next half-decade.
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It’s a significant investment for a player of that age, particularly one with recurring lower-body issues, but Bregman’s consistent offensive game, reliable third base glove and needle-moving clubhouse persona elevate the Cubs to legitimate World Series contenders. Bregman makes Chicago a better baseball team moving forward; let’s gripe about “value” some other time.
For the Red Sox, who signed the longtime Houston Astro on an opt-out-laden, short-term pact last winter, this outcome is nothing short of an utter catastrophe. Bregman’s exit from Fenway Park represents a most embarrassing culmination to a most tumultuous year. Boston’s shocking decision to trade away franchise cornerstone Rafael Devers in June was directly tied to Bregman’s presence at the hot corner.
Alex Bregman’s stint with the Red Sox was short-lived, and it appears negotiations over a no-trade clause helped prompt him to seek employment elsewhere. (Photo by Daniel Shirey/MLB Photos via Getty Images)
(Daniel Shirey via Getty Images)
Had team owner John Henry and chief baseball officer Craig Breslow committed to Bregman long-term, offloading Devers would have made some sense. Bregman’s one season at Fenway was an overwhelming success despite a two-month IL stint. Before the injury, he was tracking like a top-10 MVP candidate. The club’s gaggle of young players spoke endlessly about Bregman’s leadership qualities. His steadiness helped Boston overcome a drama-filled campaign to reach the playoffs, in which the team was a win away from knocking off the Yankees.
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Little of that matters now. The Red Sox, with their unwavering fealty to reason, didn’t want to pony up. They are left with a rightfully enraged fan base, one left perplexed at how neither Devers nor Bregman is still around. Breslow attempted to placate the Red Sox faithful via an email Q&A with Mass Live’s Chris Cotillo on Sunday, but the executive’s jargony, calculated answers only reinforced the criticism that he runs the club with a ruthless, robotic, un-human efficiency.
But even the toxically optimistic, long-viewed Breslow readily admitted that the outcome of the Bregman-Devers saga was suboptimal.
He typed out to Cotillo: “Neither outcome we face right now is ideal, but both will be evaluated over a longer time horizon.”
The rest of the interview is mostly hollow GM-speak, but there are also moments of unintentional honesty that amplify concerns about Breslow’s way of doing business. In regard to what motivated Bregman to choose Chicago’s offer, Boston’s top baseball exec said, “It would be foolish and unfair for me to guess what was most important in their decision making.”
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One might argue that rather than being “foolish and unfair,” it would be prudent and essential to understand the factors influencing Bregman’s “decision making.” The Red Sox’s unwillingness to include a no-trade clause in the contract, for instance, seems to have been a major sticking point for Bregman and his agent, Scott Boras. After two straight winters wading through free agency’s messy waters, Bregman wanted stability. He wanted somewhere he could put down roots with his family, buy a house, be part of a community, as he was in Houston. Everybody in New England knew as much.
Bregman’s desire for a no-trade clause was even more reasonable given the shadow of Devers’ departure only seven months prior. If the Sox were willing to change course and send somebody of Devers’ stature out of town, why would they hesitate to do the same with Bregman? Via additional Mass Live reporting, the team pointed to “organizational policy” in regard to their refusal to grant Bregman a no-trade. In the end, that calculating inflexibility proved to be a miscalculation.
The whole thing is a public-relations disasterclass, a textbook example of how not to interface with your fan base. Whether the Red Sox don’t know this or simply don’t care is unclear. The majesty of Fenway Park (and the surrounding real-estate holdings) ensures that the team will print money whether or not the on-field product succeeds. It’s a savvy way for Fenway Sports Group to operate. It’s also cutthroat, insulting and short-sighted.
And in the end, all will be well if the team wins. The 2026 Red Sox remain a talented bunch. Garrett Crochet is a top-four pitcher on Earth. Roman Anthony is a volcano of talent. The additions of Sonny Gray, Willson Contreras and Ranger Suárez are legitimately impactful. Positionally, the roster is a puzzle of border pieces, a disjointed assortment of good players that a trade or two could help simplify.
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Still, Boston could overcome that dynamic to win 95 games and make a deep October run. If that happens, fans will pack Fenway to the gills and champion Breslow’s commitment to the process. Success, as always in sports, heals everything.
But with Bregman out the door, it’s hard to say the Red Sox are better right now than they were a few months ago, when their season ended in pinstriped disappointment. It’s a reality that might have been avoided, whether with a couple more million or a couple more human conversations.
Either way, the result is the same: Red Sox leadership looks bad, with a long to-do list that includes explaining to an irate fan base how this happened.