Team Japan pitcher Yoshinobu Yamamoto. Yukihito Taguchi-USA TODAY Sports

Starting pitching is a clear priority for the Red Sox. Boston’s new chief baseball officer Craig Breslow acknowledged as much, although they’re certainly not alone in that pursuit.

That could extend to the top end of the market. Jeff Passan of ESPN wrote on Tuesday that the Sox were targeting front-line starting pitching. Jon Heyman of the New York Post suggests Boston is looking to add multiple starters this offseason. It stands to reason Breslow and his staff could look to pair an impact acquisition with a more affordable, if lower ceiling, addition.

Free agency offers a few possibilities. The Red Sox surely have some level of interest in Shohei Ohtani, but he wouldn’t be a factor in the 2024 rotation after his elbow procedure. Yoshinobu Yamamoto, Blake Snell, Aaron Nola and Jordan Montgomery are generally regarded as the next tier of free agent starters. AL Cy Young runner-up Sonny Gray is probably below that group in earning power because he’s 34 years old but fits in terms of short-term impact.

This afternoon, Ian Browne of MLB.com suggested in an appearance on the ITM podcast that the Boston front office prefers Montgomery to Snell or Nola (Twitter link via Steve Perrault). Sox executives chatted with Montgomery’s representatives at the Boras Corporation during last week’s GM Meetings, although they’re presumably targeting multiple Boras clients to varying degrees. (Snell is also represented by the Boras Corp.)

Montgomery turned in a 3.20 ERA through 188 2/3 innings between the Cardinals and Rangers. It was third straight sub-4.00 showing over 30+ starts. Montgomery chipped in 31 frames of 2.90 ERA ball during Texas’ run to a World Series. During the regular season, the 30-year-old southpaw struck out a near-average 21.4% of opponents while keeping his walks to a tidy 6.2% clip.

He may not have the upside of Nola or Snell, each of whom misses more bats. Montgomery has better control than Snell and hasn’t had the spotty ERA or home run issues that have troubled Nola in two of the past three seasons, however. He also has the advantage of not requiring a signing team to surrender draft compensation. The midseason trade rendered Montgomery ineligible for the qualifying offer. Snell, Nola and Gray all received the QO. Yamamoto, of course, is not subject to the QO as a foreign professional.

Roster Resource projects the Sox for roughly $189M in luxury tax commitments. That’s well below the $237M base threshold, leaving plenty of potential spending room for Breslow and his staff. It’s also possible the Sox look to the trade market for rotation help. It’s difficult to envision the Rays trading Tyler Glasnow in division. Players like Corbin Burnes or Shane Bieber could be available as they enter their final seasons of arbitration eligibility.

Boston’s current rotation mix is a high-variance unit. Nick Pivetta, Chris Sale, Brayan Bello, Tanner Houck and Garrett Whitlock have all shown substantial upside.They also come with uncertainty to varying degrees. Houck and Whitlock might be better suited for relief. That could also be true of Pivetta, although he finished the 2023 season pitching very well over multiple innings. Sale has battled injuries and Bello seemed to wear down in the second half of his first full MLB season.

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