There are some items that can, no doubt, be placed near the top of the Red Sox‘s offseason to-do list. Re-signing Alex Bregman is surely there, and the Red Sox have been blunt about that. Adding another power bat, too, is an obvious one. Perhaps a bit further down, though, is this: putting a true No. 2 starting pitcher behind Garrett Crochet in the rotation.
Brayan Bello had a breakthrough year, but even at his best, he is likely a No. 3 option. Lucas Giolito was great at times, too, but the injury issues that flared up late in the year are a big question mark. Giolito can potentially be a free agent, too, and it’s not clear whether the Red Sox will bring him back.
Boston has much-improved depth in the rotation heading into 2026, both among veterans who got a taste of regular rotation spots last year–Hunter Dobbins, Richard Fitts, Kyle Harrison–and young prospects who could earn spots. We saw Payton Tolle and Connelly Early make exciting debuts in Boston, and the organization has made stocking the farm system with arms in the draft a priority.
But there’s not clear No. 2 here. And that needs to change.
Red Sox Need a No. 2 Starter, and Joe Ryan Fits
It’s no secret that the Red Sox were in talks with the Twins at the deadline on a package that would have brought back pitcher Joe Ryan, and there’s been amply speculation that the two sides will re-ignite those talks this winter.
Ryan qualifies as a quality No. 2 for Crochet. He is 29 was an All-Star this season, going 13-10 with a 3.65 ERA for the Twins. in 171.0 innings, he struck out 194 this season, sixth in the American League.
It was especially hard to trade for Ryan this season because he does have one more year of team control, projected to be at $6 million by Spotrac.
Star Outfielder, Exciting Young Pitcher on the Way Out?
On “The Fenway Rundown” podcast, starring longtime Red Sox insider Sean McAdam and beat writer Chris Cotillo of MassLive, the subject of a potential Ryan trade was raised.
And according to McAdam, the starting price for a Ryan trade will be one of the Red Sox’ trio of quality outfielders–Jarren Duran, Wilyer Abreu or Ceddanne Rafaela–plus one of the impressive young pitchers we saw in 2025.
“If you start a Joe Ryan package,” McAdam said, “with one of your major-league outfielders and one of the pitchers that broke through—whether that be a Dobbins or an Early or a Tolle, I know those are varying degrees of value. I think you probably can get something done for anybody, especially if you include Duran or Abreu or Rafaela. They’re not trading (Roman) Anthony, they’re not trading (Marcelo) Mayer or (Kristian) Campbell …
“Maybe you sell high on Early. There are a lot of combinations.”
Getty Images)Connelly Early #71 of the Boston Red Sox.
Red Sox Might Tick off Some Fans
Cotillo pointed out that the Red Sox, if they’re to make a major trade this winter, are probably going to anger some fans. That’s because the team’s most coveted talent are the young players who have already made an appearance on the big-league roster and have plenty of fans.
“They’re going to do something that (ticks) off fans—not in a bad way—but by trading away a player you know. … They’re going to trade somebody who excited you whether it be an Early or a Tolle or a Duran,” Cotillo said. “It’s going to be somebody in that bucket because that’s where the talent is.”
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