The Red Sox have always ranked among the league’s heavyweights in terms of financial resources, but throughout the club’s recent five-year rebuild, ownership seemed content to hold back. The Red Sox spoke about sustainability while accepting mediocrity, and every winter they largely sat on the sideline, much to the frustration of the club’s fans.

Last winter that approach began to change.

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In 2025 the Sox finally began acting with urgency. The club signed Alex Bregman to a deal valued at $40 million per season, acquired Garrett Crochet in a blockbuster trade and gave him the second largest contract to a pitcher in franchise history, and dished out lucrative in-season extensions to Roman Anthony, Aroldis Chapman and Kristian Campbell.

Coming off the club’s first postseas

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