Red Sox Rotation Puzzle Just Got More Complicated For 2027

Will the Red Sox make strategic roster adjustments to acquire Cubs' All-Star Shota Imanaga, despite their already left-heavy rotation?

The Red Sox may already be sitting on one of baseball’s better starting rotations, but that hasn’t stopped one prominent insider from floating a familiar name as a possible add.

MLB.com’s Ian Browne pointed to Cubs left-hander Shota Imanaga as a pitcher who could make sense for Boston, especially if Sonny Gray ends up elsewhere. Browne also noted that Craig Breslow was high on Imanaga years ago while scouting him for Chicago.

“Even if the rotation looks to be a strong suit, you can never count out [Craig Breslow] from adding more rotation depth, particularly if Gray signs elsewhere,” Browne wrote. “One name that intrigues me?

Shota Imanaga. Breslow was really fond of him when he was scouting him for the Cubs three years ago.

The Cubs wound up signing him, but Breslow was in his early stages with the Red Sox at that point.”

Imanaga’s track record makes the idea easy to understand. He posted a 3.77 ERA in 32 starts in 2026, throwing 174 1/3 innings for Chicago. Before that, he logged a 3.73 ERA in 25 starts in 2025, and in 2024 he broke in with a 2.91 ERA across 29 starts as a rookie, earning the lone All-Star selection of his career so far.

The problem for Boston is less about ability and more about fit. Imanaga throws left-handed, and the Red Sox already have a rotation that leans that way heavily. Garrett Crochet, Payton Tolle, Ranger Suarez and Jake Bennett are all lefties, and the club is unlikely to roll into a season with an all-left-handed starting five.

That creates the real wrinkle here: if Boston were to pursue Imanaga, someone else would have to move around. Crochet, Tolle and Suarez look like they’re staying put, which leaves Bennett as the most logical piece to consider in the right deal. The source article even points to a scenario like an Elly De La Cruz-type return as the kind of move that could make Bennett available.

So yes, Imanaga is a legitimate name to watch, and the interest from a Red Sox insider is notable. But if Boston ever got serious, it would take some roster maneuvering to make the fit work.

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One name now on the radar is Kaima Taira, the Japanese free-agent pitcher recently posted by the Seibu Lions, according to ESPN insider Kiley McDaniel. Taira just turned in a breakout season as a starter in Nippon Professional Baseball, and the Red Sox could have a narrow window to make their case because the posting period for NPB free agents is expected to be shortened with an MLB lockout looming. [Read more 🡒]

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The names likely to surface are the ones Boston would hate to move but might have to consider if the right return materializes. Jarren Duran and Wilyer Abreu both fit the profile of players who could draw attention in talks, while Miamis pitching depth could make this more than a simple check-in. Max Meyer is one of the arms that could enter the conversation, but for now it remains just that - a conversation, with no deal yet in place. [Read more 🡒]