Boston Red Sox face critical offseason decisions that could reshape their 2026 World Series aspirations. Should they trade first baseman Triston Casas despite his elite potential, or wait for him to prove his durability after consecutive injury-plagued seasons?

Gabby (Hurlbut) Maljanian analyzes Craig Breslow's aggressive offseason strategy, breaking down why trading Casas now—while his value remains high—could unlock deals for ace pitching like Tarik Skubal or Joe Ryan. The discussion covers Garrett Crochet's legitimate Cy Young candidacy against Detroit's Skubal, examining advanced metrics that reveal why Boston's new ace posted 255 strikeouts across 205 innings. Roman Anthony's impressive rookie campaign gets scrutinized, including how his third-place Rookie of the Year finish cost him $3 million in bonuses and what his defensive improvements mean for the outfield logjam.

Key topics include potential trade packages involving Jarren Duran, Pete Alonso as a power-hitting replacement, and why the Twins, Tigers, Royals, and Mariners make ideal trade partners.

Discover why this offseason could define the Red Sox's championship window for years to come.

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