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Cotillo: How Alex Bregman’s departure makes Rafael Devers trade even worse for Red Sox
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- Cotillo: How Alex Bregman’s departure makes Rafael Devers trade even worse for Red Sox
Just when you thought it was impossible for there to be more discourse over the months-long saga that ended with the Red Sox trading Rafael Devers to the Giants in June... here we go again.
With Devers’ third base replacement, Alex Bregman , bolting Boston for Chicago and signing a five-year, $175 million deal with the Cubs , it’s worth re-litigating the series of events that led to the Devers trade in June. Eleven months after it was easy to dream on both multi-time All-Stars forming the nucleus of Boston ’s lineup for years to come, both are gone. And it simply didn’t have to be this way.
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The Red Sox underestimated how Devers would react to a potential move off his natural position, then months later, underestimated how difficult it would be to bring Bregman back on a long-term basis. The original sin was poor communication with Devers, who is far from faultless in the rift that led to his eventual departure. But even if someone needed to squint to understand and eventually accept why the Red Sox shipped Devers west, it would be done with the understanding that Bregman wouldn’t be a one-year rental. In the context of the Devers deal, letting Bregman walk is unacceptable, if not borderline inexplicable.
With Alex Cora and Sam Kennedy leading the charge, the Red Sox were clearly enamored enough with Bregman, in terms of both on-field impact and intangibles , to get somewhat uncomfortable, not necessarily with the financial commitment (effectively, a highly deferred one-year, $40 million deal) but certainly with the chance for clubhouse chaos. It was always a risky play to insist to Devers that he was the third baseman of the future while quietly pursuing Bregman, then employ a forgiveness-over-permission approach while asking Devers to do what was best for the team and move to designated hitter. That risk was worth taking, in the minds of the Red Sox, because of what they were getting in Bregman, a proven winner, clubhouse leader and defensive upgrade at third base. Even if Devers gets angry, club officials must have thought, what’s the worst that could possibly happen? By the end of spring training, when Devers was telling confidants he wanted out, the Red Sox were beginning to get their answer.
Things were tenable by Opening Day, when the Red Sox had Devers hitting second and Bregman hitting third as the season started in Texas . That stopped being the case in early May, when after Triston Casas went down with a season-ending knee injury, Craig Breslow asked Devers if he’d take up first base. The Red Sox might have expected him to be reluctant to that. They did not anticipate how ardently.
With Devers enraged a second time in a three-month span — and untouched by the drastic measure of principal owner John Henry flying halfway across the country to talk to him – the Red Sox ultimately deemed the situation untenable and filed for a dramatic divorce by booting Devers off a team flight to start his journey to San Francisco . In the shock and awe of it all, at least they had Bregman to fall back on. So they thought.
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It’s not clear if the Red Sox went to Bregman, who was injured at the time of the Devers trade, and made a real effort to extend him with the dollars (in excess of $250 million) saved by the Devers deal and pressure to reallocate that money building. If they didn’t, they should have. It takes two to tango, especially when one dance partner is a Scott Boras client. But Bregman liked Boston enough to at least entertain a deal and if the Sox blew him away — think what the Cubs actually offered him, but in June while on the injured list — there was probably a pathway to an agreement. Instead, the Sox banked on another subpar market for the former Astro. Club officials wondered aloud where Bregman would find his long-term deal considering he was a year older, had a significant injury in 2025 and didn’t have the market he wanted last winter. On Saturday night, everyone found out.
The Red Sox’ efforts to retain Bregman weren’t feeble by any means, but the club once again didn’t reach the point of discomfort necessary to get their man. It wasn’t a case of Bregman actively wanting to go elsewhere after a solid year in Boston. If an offer made sense, he’d be happy to return. Ultimately, the differences between the two proposals — annual value, no-trade protections and a deferral schedule that stretched out decades — were too much for emotions to matter . Bregman is Chicago bound and the Red Sox are left scrambling.
In a vacuum, it might be a smart baseball move that the Red Sox decided it was too risky to give $35 million per year to Bregman through his age-37 season. That deal, like many of its kind, might not age very well. There’s still even a chance the Red Sox pull a Bo Bichette-sized rabbit out of a hat or find other ways to get creative and put a better team on the field on Opening Day than they did in 2025. Bregman’s departure, alone, might not sink Boston’s chances of contending next season.
But with the shadow of the Devers debacle looming, the Red Sox couldn’t let Bregman, too, get away. It’s fair, now, to reason that the club lost its franchise player, who just two years prior had signed the largest contract in franchise history, to accommodate a player who wound up playing just 86 more games — including three in a brief postseason cameo — in a Red Sox uniform. The roadmap to disaster was a convoluted, windy one. The end destination was the result of malpractice.
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The onus is now, more than ever, squarely on Henry, Kennedy, Breslow and everyone else with an office on Jersey Street to reallocate the money first put aside for Devers, then later Bregman, in a big way. Not in the form of retaining, extending, buying a depreciated asset or creatively trading . The big-market Red Sox of yesteryear would right their wrongs by paying up when the opportunity emerged. In Bichette, there’s a clear window for such a move.
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