Coming off an 89-win season and their first playoff appearance since 2021, the Boston Red Sox are heading into a pivotal offseason as they look to go from Wild Card team to World Series contender.
One area where the Red Sox need to improve is the starting rotation, where they still need a true No. 2 starter behind Garrett Crochet after failing to acquire one at the trade deadline. While they have plenty of pitching depth, the staff could use another top-of-the-rotation arm to slot in behind Crochet, similar to how Boston traded for Chris Sale to pair with David Price after the 2016 season.
Fortunately for the Red Sox, there are several frontline starters that could be on the trading block this winter, including Hunter Greene, Tarik Skubal and Joe Ryan. There will also be several star hurlers available in free agency, including Dylan Cease, Michael King, Merrill Kelly and Zac Gallen.
Given Boston’s financial resources, strong farm system and urgent need for a top starter, MassLive’s Chris Cotillo expects Craig Breslow to land a No. 2 starter this offseason one way or another.
“The prediction here is that for the second straight winter, Breslow does some high-end shopping when it comes to the rotation,” Cotillo writes. “The Red Sox need someone like Ryan, Cease, King or Gore to pitch Game 2 of a postseason series next fall. Breslow knows that and will likely act accordingly.”
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Cotillo believes Boston may prefer the trade market if Lucas Giolito returns, potentially on a one-year, $22.025 million qualifying offer. If Giolito leaves, however, the team will have more money to spend on a starter and may go the free agency route instead, especially after trading considerable prospect capital for Crochet, Dustin May and Steven Matz over the last 12 months.
Either way, Cotillo expects Breslow to make a big move to upgrade the rotation this winter, which is exactly what the Red Sox need.
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