The Red Sox have a handful of needs to address this Major League Baseball offseason, but one stands alone as the most pressing.

Boston must bolster its starting pitching depth this winter if it wants to return to the playoffs in 2024. Red Sox starters combined to rank near the bottom of the league in most notable pitching metrics last season, and the club absolutely could benefit from adding a headliner to the rotation.

That addition could prove to be Jordan Montgomery, who is among Boston’s “top targets” this offseason, per The Athletic’s Jen McCaffrey. The Red Sox reportedly had an in-person meeting with Montgomery’s agent, Scott Boras, earlier this month and Boston apparently entered the offseason preferring the veteran southpaw over fellow free agents Blake Snell and Aaron Nola, who re-upped with the Philadelphia Phillies.

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The pieces might be in place for Montgomery to land with the Red Sox, too. Craig Breslow and company have the money to give the 30-year-old the contract he likely covets and Montgomery currently is getting a real feel for Boston. The left-hander reportedly is living in proximity of Fenway Park while his wife serves as a dermatology resident at a Boston-area hospital.

What would it take for the Red Sox to ink Montgomery? The Athletic projects the 2023 World Series champion to sign a five-year, $105 million deal.

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