His family’s comfort was an equally important factor. Bregman and his wife, Reagan, have two sons, 3-year-old Knox and 9-month-old Bennett. They appreciated the lengths the Red Sox go in creating a family-friendly environment for the players at the ballpark.
That helped to explain why Bregman insisted on a full no-trade clause in his contract. He didn’t want his family to establish roots in Boston only to wake up one day and learn he had been traded.
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If that seems unlikely, it shouldn’t. Chief baseball officer Craig Breslow is two years and two months into the job. His three predecessors — Ben Cherington, Dave Dombrowski, and Chaim Bloom — lasted an average of four years and two months. Things change fast with the Sox.
Bregman didn’t want to risk the Sox ownership shifting lanes again and hiring an executive who saw him as trade chip. He was prepared to accept five years and $165 million until the team balked at the no-trade clause and insisted on deferred payments that reduced the present-day value of the contract.
Had the Sox granted him no-trade protection and negotiated more favorable deferrals, Bregman would still be with the team, according to a source familiar with the process. Instead he was told this was the team’s final offer.
Alex Bregman seemed to check a lot of boxes for the Red Sox, both on the field and off.Matthew J. Lee/Globe Staff
That was when Bregman turned to the Cubs. Chicago offered a five-year contract worth $175 million with a better deferral schedule and no-trade rights. Bregman accepted those terms on Saturday.
Chris Sale received full no-trade rights from the Red Sox in 2021 as part of the contract extension he agreed to in 2019. He waived those rights when Breslow traded him to the Braves in 2023 for infielder Vaughn Grissom.
It’s unclear if the Red Sox now have a blanket policy against no-trade clauses or if it only applied to Bregman. Breslow did not respond to a question about that aspect of the negotiations.
Either way, the Sox miscalculated what was important to him.
The Sox also appear to have underestimated his options. They signed Bregman after spring training opened last season when he was running out of time to find a team and adequately prepare for the season. Bregman had better alternatives than the Tigers this time around as agent Scott Boras successfully marketed him as a two-way player who brought value on defense.
The Cubs were a 92-win team that lost a five-game Division Series last season. They see Bregman as a player who can help get them into the NLCS and beyond.
The Cubs have become one the more data-driven teams in the game under president of baseball operations Jed Hoyer. Breslow worked for Hoyer from 2020-23, rising to assistant general manager. Their views on a player did not align this time.
The Red Sox have ample time to improve their roster with the first full-squad workout of spring training still more than a month away. Infielder Bo Bichette would fit their lineup well and is four years younger than Bregman. But that also means he is likely to want a longer-term, more lucrative deal.
Fellow free agent Eugenio Suárez belted 49 homers for the Diamondback and Mariners last season. But he is strikeout-prone and a poor defender. Or the Sox could improve at positions other than third base via free agency or trade.
In Bregman, they had a player who fit their lineup, their ballpark, and their clubhouse. He also welcomed the expectations that come with playing in a market like Boston, something not every player finds attractive.
Teams tend to embrace such players. This time the Red Sox threw up obstacles.
Peter Abraham can be reached at [email protected]. Follow him on Bluesky at peteabeglobe.bsky.social.
