Red Sox Linked to Cubs' Shota Imanaga, But There's a Major Catch

The Boston Red Sox may end up needing a starter this winter. Could the Chicago Cubs All-Star be the answer?

Sep 16, 2026; Chicago, Illinois, USA; Chicago Cubs pitcher Shota Imanaga (18) delivers the ball during the first inning against the Atlanta Braves at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect

The Boston Red Sox already have the makings for one of the best overall starting rotations in baseball, and there's room to add.

If the 2027 season were to start today, the Red Sox's likely starting rotation would be Garrett Crochet, Ranger Suarez, Payton Tolle, Jake Bennett and Brayan Bello. Tanner Houck could figure into the mix as well, but Bello should have the inside track to the last rotation spot, among internal options. If Sonny Gray was still a member of the organization, he'd be a lock as well and either would push out Bello or Bennett. But the three-time All-Star is a free agent and there's no guarantee he will be back. But there are other external options who could replace him. For example, MLB.com's Ian Browne pointed to Chicago Cubs All-Star Shota Imanaga as an option, but there's a catch.

"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."

Shota Imanaga As A Fit For Boston

Sep 4, 2026; Miami, Florida, USA; Chicago Cubs pitcher Shota Imanaga (18) returns to the dugout against the Miami Marlins during the second inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | IMAGN IMAGES via Reuters Connect

There's no denying the fact that Imanaga is a great hurler. He had a 3.77 ERA in 32 starts in 2026 as a member of the Cubs across 174 1/3 innings pitched. In 2025, he had a 3.73 ERA in 25 starts for the Cubs. In 2024, he had a 2.91 ERA in 29 starts as a rookie and earned the lone All-Star nod of his career to this point.

He has the talent to help Boston, but he's left-handed, which the Red Sox are loaded with. Crochet, Tolle, Suarez and Bennett are all left-handed. Simply put, the Red Sox are not going to enter a season with their entire starting rotation being left-handed. That's easier to plan around than it is to mix in righties as well. So, if the Red Sox were to bring Imanaga to town, what do you do with the other lefties?

Crochet, Tolle and Suarez aren't likely to go anywhere. Bennett, on the other hand, could make sense as a trade chip in the right scenario, like Elly De La Cruz, for example.

Imanaga is great and it's interesting that one of the Red Sox's prominent insiders mentioned him as a fit. Arguably, he wouldn't be a seamless fit to replace Gray without some roster gymnastics. But he still should be considered if the right move comes along.