The Boston Red Sox had quite an exciting offseason and season over the last year, but this winter’s offseason could be even more exciting.

Boston has multiple pieces from their 2025 club who are set to land in free agency, headlined by Alex Bregman. The Red Sox could look to bring some of their guys back, but they could also sign outside players to help bolster the roster.

Bleacher Report’s Tim Kelly recently discussed Lucas Giolito as a free agent and listed the Red Sox starter as one of the top 10 starting pitchers in free agency this winter.

Sep 17, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Lucas Giolito (54) pitches against the Athletics during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images / Eric Canha-Imagn Images

“We didn’t put players with options that are sure to be exercised—like Chris Sale and Freddy Peralta—on this list. Giolito has a mutual $19 million option for 2025, and both the pitcher and the Boston Red Sox could go either way on that,” Kelly wrote. “The most likely scenario is that Giolito declines the option, because if he does, the Red Sox could very well extend a one-year qualifying offer to him, which would pay him around $22 million. Again, it’s possible he takes that. It’s also possible he declines it, or even that the Red Sox don’t extend it to him. There are a lot of moving parts here.

“If Giolito gets to the open market, he pitched very well after missing the entirety of the 2024 season after undergoing an internal brace procedure on his right elbow. Giolito wasn’t available for what turned out to be a brief postseason run with the Red Sox because his elbow flared up. Ultimately, pretty much all of this is contingent on him being healthy heading into the offseason.”

Giolito’s free agency is likely going to hinge on his health. He can accept the qualifying offer from the Red Sox, if they extend it, and nobody would bat an eye. Signing back with Boston for over $20 million on a one-year deal would work well for both sides.

But Giolito could decline the qualifying offer and bet on himself in free agency. There’s a chance he’s chasing a three- or four-year contract worth around $20 million a year.

In the past few offseasons, there have been numerous free agent pitchers sign for over $60 million or $70 million, with Giolito being better than multiple big contract pitchers.

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