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The Boston Red Sox made the biggest trade of the Winter Meetings by acquiring Garrett Crochet. They sent four of their top 15 prospects to the Chicago White Sox for the lefty starters. But after a disappointing season, they need more than just one pitcher. The Red Sox should hit free agency to add Alex Bregman to their 2025 squad.
The Astros legend hits free agency after nine seasons in Houston. He is not a lock to leave Space City just yet, as they have offered him a contract that should be competitive. But the Red Sox have not spent big money in free agency since signing David Price before the 2016 season. They must buck that trend by signing Bregman to a massive contract.
The Red Sox did spend money this season by retaining manager Alex Cora. He was in the last year of his contract and rumors were swirling that his time in Beantown could be ending. But Cora signed a three-year extension worth over $7 million per season. He was hired after a successful run as the bench coach in Houston.
There is a history between Cora and Bregman, one an Astros hater would tell you involves cheating their way to a World Series. But familiarity is important in free agency and the Red Sox have that over other involved teams. He is also a fit for Boston, a team full of left-handed hitters.
Rafael Devers could make the move from third base to first base if Bregman comes to the Red Sox. That would make Tristan Casas available via trade, which could mean another big addition to their starting rotation. Adding Bregman does not have to be the last addition while also keeping payroll relatively low.
The Red Sox signing Alex Bregman would mean trading Tristan Casas
Casas is one of the many young left-handed hitters on the Red Sox. Between Devers, Jarren Duran, Wilyer Abreu, and Masataka Yoshida, they have plenty of lefties. Adding Bregman and trading Casas would even out the lineup and add a needed veteran to this young core.
Garrett Crochet could be the final piece to a great starting rotation for the Red Sox. With 2024 All-Star Tanner Houck, Crochet, Lucas Giolito returning from injury, and Kutter Crawford, they are in solid shape. But Casas could net a massive pitching arm in return from a team looking to add a bat.
The Seattle Mariners had a wacky 2024 season that ended with an epic collapse to miss the playoffs. They were one of the best pitching teams in the league but finished second-to-last in team batting average. Casas missed much of the 2024 season with an injury but could be the young lefty they attach to Julio Rodriguez in the lineup.
The Red Sox should ask for Luis Castillo in return. The veteran has four years left at over $24 million per season but there can be money retained by Seattle that makes the deal work. Castillo and Bregman would both be expensive but the Red Sox have to spend money to catch up to the Yankees and Orioles in their own division.
By making these moves, the Red Sox can shoot to the top of the wide-open American League. The Yankees lost Juan Soto, they would have taken Bregman from the Astros, and the Guardians have not added anyone yet. While it has been a rough half-decade for Boston fans, this could be the offseason that powers them out of it.
