The Boston Red Sox were eliminated from the MLB postseason by the New York Yankees in an embarrassing AL Wild Card Series in New York.

With the 2026 season over for the Red Sox, they now need to look to the offseason to try to upgrade this team for a deeper postseason run in 2027. There are plenty of areas worth exploring, but one has emerged as a big priority.

ESPN's David Schoenfield revealed that the starting rotation is their top priority this offseason. But why? With Sonny Gray set to hit free agency, on top of a lot of pitchers leaving the organization recently, adding rotation help is a must this winter.

Why Red Sox are in desperate need of rotation help

"A healthy Garrett Crochet will help fill that void, but after trading away so many starting pitchers and pitching prospects over the past year," Schoenfield writes, "... adding depth in that department looks necessary."

The Red Sox are looking likely to lose Gray in free agency or to retirement this offseason. If he's out, the Red Sox will need some help to bolster their rotation.

Payton Tolle, Ranger Suarez, and a healthy Garrett Crochet should help, but relying on Jake Bennett to continue his breakout isn't a good idea.

At least not with Brayan Bello, Tanner Houck, Kutter Crawford, and Johan Oviedo as the team's other options on the MLB roster.

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Add in that the Red Sox have recently traded away Kyle Harrison, Anthony Eyanson, Hunter Dobbins, Shane Drohan, Connelly Early, and Kyson Witherspoon, and pitching upgrades are a must this offseason.

Fortunately, it's a good time to need starting rotation help, as the pool of free-agent starters is very vast this year. Tarik Skubal would be the dream pickup, but pitchers like Shota Imanaga, Kevin Gausman, Casey Mize, and Robbie Ray would make more sense.

Even though the starting rotation might not seem like the biggest need, the questionable depth could really hurt the team next season. So, a pitcher or two this winter would make a lot of sense for the Red Sox.

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