Craig Breslow has never kept the off-season plan a secret. After the Boston Red Sox’s season ended with a loss to the Yankees in the AL Wild Card series, the message was on the wall—the Boston Red Sox need pitching. They needed more help in the rotation behind Crochet, and Breslow said he wanted to add at least one new starter.

But what happened next was strange. Instead of adding an arm, they let one go, and just like that, Lucas Giolito hit free agency. Breslow’s reluctance, though, is not something Giolito is holding a grudge over.

The 31-year-old spoke about how things stand between the team and him, and for him, it’s all about acceptance. He loved his time in Boston and would love to be back, but if they don’t bring him back, he understands that, too.

“I loved it there, and I would have loved to go back,” Giolito said. “I still would, but if you look at the writing on the wall, I don’t think they need another starting pitcher. That’s business, baby! That’s how it goes.”

That summed up exactly how Giolito is handling the free agency this time around. He said that it feels very different from the last time he was in the market. Back then, everything felt heavy, but this time, he is mostly focused on his work.

He is training six days a week now and spending time dialing in mechanics, adjusting the pitch mix, and even trying to add another pitch. Plus, instead of worrying about the rumors or which teams will be into it, he is leaving the things to his agent—until some real, credible offer shows up. He deserves a nice payday, though, given he surpassed 140 innings in 2025, finishing with a 3.41 ERA across 26 starts.

He had declined the mutual option on the two-year, $38.5 million deal he signed with the Red Sox, hoping that things would look up from here. But as Boston clearly has a shift in focus, Giolito has made peace with the situation.

Meanwhile, the front office—they are all but seemingly looking confused this season.

The story of the Red Sox’s unfinished winter

The Boston Red Sox were fiery in the postseason, or at least they were when they first came in 2025. It has been anything but calm since then. With 87 days to go before the opening day, their winter has been active, a whole lot chaotic, and unresolved.

Now it is true that their run ended quickly against the Yankees, but last season’s 89-73 finish showed that they are progressing. They had far too many years tearing up about being the backbenchers of the league. Chief Baseball Officer Craig Breslow clearly agreed—and moved quickly to build on it.

They traded for Sonny Gray, which brought the much-needed stability to the rotation. They added Willson Contreras, who reshaped the lineup with a tough, right-handed bat and also postseason experience. These were not flashy moves, but they were smart ones.

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Still, they didn’t finish the job.

Everything shifted when Bregman opted out of his contract. Boston would like to keep him, but suddenly, a spot that they thought was settled is wide open again. Resigning Bregman would mean good, but moving on also could mean a dramatic change, and when Bo enters the conversation. He lingered around the Boston off-season, and sure, he was not loud, but he was persistent.

Meanwhile, Jarren Duran’s name has popped up in trade talks, and that kind of chatter doesn’t happen unless something real is being considered.