The Boston Red Sox began the 2025 season with what they thought was plenty of starting pitching depth, but they ran out of luck just before the calendar flipped to October. Lucas Giolito was sidelined with an elbow injury for the Wild Card round, which left the Red Sox with just three starters for their postseason run.
Boston's late-season desperation has many reporters placing starting pitching high on its list of offseason needs. Chief baseball officer Craig Breslow has been intently focused on improving the Sox's pitching since his arrival in the front office, so it makes sense to expect him to bolster the rotation after their return to the postseason for the first time in four seasons.
The Red Sox could add to their pitching staff via the free agent or trade market — they have the resources to make good use of both. But MLB insider Jim Bowden believes they'll stick to one market to strengthen their staff (subscription required).
"The Red Sox are focused on adding starting pitching, and they have plenty of prospects in their strong farm system to perhaps trade for top arms like Tarik Skubal, Hunter Greene or Freddy Peralta. They also have the financial freedom to land one of the top starters in free agency, though trading for a top-tier starter is their preferred route," Bowden wrote.
MLB insider Jim Bowden believes Red Sox will stick to trade market for offseason pitching reinforcements
This report doesn't come as a total surprise for many Sox fans. Boston's farm system has been a hot topic of discussion around MLB in recent years due to its previous crop of top prospects — most of whom have reached the big leagues. But Breslow has replenished the Sox's prospect pool with top-tier pitching talent from the last two MLB Drafts, and other teams may covet young arms like Payton Tolle, Connelly Early, Brandon Clarke, Kyson Witherspoon and more.
Bowden mentioned aces Skubal, Greene and Peralta could be available on this year's trade market, and the free agent market won't match up with that level of talent. Framber Valdez, Michael King, Dylan Cease, Ranger Suárez, Nick Martinez, Chris Bassit and Shota Imanaga lead the charge among the top free agent pitchers available, but none suit the Red Sox's needs quite as well as any of the pitchers they've been linked to via trade.
The Red Sox don't have enough room on their roster for every top prospect in their system, and they should trade some of them for elite pitching while there is plenty of time in their contending window. Boston's deep prospect pool doesn't justify not spending on any free agents, but this year's crop of pitchers is rather underwhelming compared to who it may be seeking to add.