Inside The Pinstripes

Yankees Could Land Red Sox Free Agent

The New York Yankees have missed out on some of the top free agent starting pitchers, but could land a recent Boston Red Sox arm for depth.
Sep 12, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Lucas Giolito (54) delivers a pitch during the second inning against the New York Yankees at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images
Sep 12, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Lucas Giolito (54) delivers a pitch during the second inning against the New York Yankees at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images | Paul Rutherford-Imagn Images

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The New York Yankees still need rotation depth this winter, and their recent tepid pursuit of Edward Cabrera signaled that they're still in the market. They've missed out on some of the best available free agent starters, but they still have options on the board for depth pieces.

In a recent MLB Network appearance, broadcaster Jon Morosi suggested that the Yankees may be likely to go after a starting pitcher like Boston Red Sox free agent Lucas Giolito, who would be a realistic but underwhelming depth option.

"It doesn't have to be a Framber Valdez or a Ranger Suarez or a high-profile trade like those we were discussing -- and by the way I don't think Tarik Skubal is going to be a Yankee, at least not now," Morosi said. "Maybe in July, we'll check back on that [...]."

Boston Red Sox pitcher Lucas Giolito
Aug 26, 2025; Baltimore, Maryland, USA; Boston Red Sox pitcher Lucas Giolito (54) reacts to a strikeout to end the eighth inning against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

"But I think right now for the New York Yankees, they're probably looking more for the depth names; names like Lucas Giolito is out there, and I hesitate to call someone like Zac Gallen depth, but it's more the number three starters or below."

Giolito is High-Risk

Giolito, who will be 32 in July, logged a 3.41 ERA in 2025 but missed the postseason due to elbow soreness, which the Yankees may take as a signal that he isn't worth the risk.

At the moment, the Yankees have Carlos Rodon and Gerrit Cole slated to come back from surgeries in 2026, likely after the spring, and likely not back to form right away. Luis Gil, who came off his own injury in 2025, struggled in the wake of it and required time to return to full strength. The Yankees should expect this to be the case for their star starters, but they aren't acting like it.

New York Yankees pitcher Gerrit Cole
Mar 6, 2025; Tampa, Florida, USA;New York Yankees pitcher Gerrit Cole (45) pauses before taking the mound against the Minnesota Twins during the first inning at George M. Steinbrenner Field. Mandatory Credit: Dave Nelson-Imagn Images | Dave Nelson-Imagn Images

So far, the Yankees missed out on Tatsuya Imai, who they lost to the Houston Astros after, apparently, not putting up much of a fight for him. A report from MLB Insider Jon Heyman revealed that they never even made an offer for the Japanese starter, and saw him "as a reliever" while other MLB teams courting him viewed him as a mid-rotation starter.

As for Cabrera, Heyman also revealed that the Yankees were "not close" to signing him before he headed to the Miami Marlins.

The Yankees need another arm, but a high-risk arm like Giolito might not be the solution to their problem. What they need is someone more likely to stay healthy, and they keep missing the mark on their best opportunities.

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Published
Erin Shapland
ERIN SHAPLAND

Erin covers the New York Yankees for On SI, reporting on all aspects of the championship chase that comes with a storied franchise. A fan of all storylines, who's looking to bring the latest news and updates to one of professional sports' greatest fanbases.