BOSTON, January 5, 2026 — The Boston Red Sox have dramatically reshaped their roster this offseason, and according to MLB senior writer Jim Bowden, they’re now among the seven most improved teams in baseball.
A Winter of Wheeling and Dealing for Boston
Craig Breslow has been aggressive in trades, bolstering the Red Sox lineup and pitching staff.
- The Red Sox acquired three-time All-Star Sonny Gray in a November trade with the St. Louis Cardinals.
- Right-hander Johan Oviedo joined the rotation in early December via a deal with the Pittsburgh Pirates.
- Boston landed three-time All-Star first baseman Willson Contreras in a mid-December trade, again working with former chief baseball officer Chaim Bloom.
- The team continues to prioritize re-signing All-Star third baseman Alex Bregman.
Boston’s biggest moves have all come through trades, each involving a team from the National League Central division. The Red Sox first landed three-time All-Star starting pitcher Sonny Gray in a November deal with the Cardinals. Then, in early December, they brought in right-hander Johan Oviedo in a trade with the Pirates, adding depth to the rotation.
What’s the biggest upgrade the Red Sox have made this offseason? The acquisition of three-time All-Star first baseman Willson Contreras is a significant improvement at the position, and he is expected to become the everyday starter, surpassing Triston Casas and others.
Bowden, formerly a general manager himself, highlighted the impact of these moves in a Monday analysis. “Boston traded some good prospects that Bloom was really high on for starter Sonny Gray and first baseman Willson Contreras,” he wrote. “Gray is the Red Sox’s new No. 2 starter and slots behind their ace Garrett Crochet. Contreras is a significant upgrade at first base…Red Sox chief of baseball operations Craig Breslow also improved the rotation depth by trading more prospects for Johan Oviedo and completing a prospect challenge trade, sending right-hander Luis Perales to the Nationals for left-hander Jake Bennett, who is closer to big-league ready than Perales.”
While Breslow traded away a portion of their farm system depth, he managed to hold onto the team’s very best prospects throughout these transactions.
Despite missing out on free-agent sluggers like Kyle Schwarber and Pete Alonso, Bowden believes the Red Sox aren’t finished making moves. “The Red Sox are not done making moves, as they remain in the running for Bregman, Bichette and Eugenio Suárez, among others,” he noted.
Reports indicate that the team’s “priority” remains re-signing All-Star third baseman Alex Bregman, signaling their continued pursuit of impactful players to further strengthen their roster.
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