The Boston Red Sox and Pittsburgh Pirates have become frequent trade partners in recent seasons. Boston and its former general manager Ben Cherington, now in charge in Pittsburgh, have swapped Enmanuel Valdez for minor league pitcher Joe Vogatsky, Nick Yorke for Quinn Priester and Jhostynxon Garcia for Johan Oviedo.
The Red Sox will seemingly give former chief baseball officer Chaim Bloom — current president of baseball operations with the St. Louis Cardinals — the same treatment. Craig Breslow traded for Cardinals starter-turned-reliever Steven Matz at the 2025 trade deadline and made a shocking deal for starter Sonny Gray early in the 2025-26 offseason.