With the 2025 Red Sox season over and an important offseason approaching, it’s time to break down each part of the Red Sox’ roster entering what should be a busy winter for chief baseball officer Craig Breslow. All week, we’ll be running a five-part series analyzing each part of Boston’s roster. First up is a look at Boston’s starting rotation entering 2026:

WHERE DO THINGS STAND?

In a much different place than they did this time last year, when Breslow was searching for a bonafide ace. The impact of the addition of Garrett Crochet can’t be overstated, as it raised both the ceiling and floor of Boston’s rotation tremendously. Now, it’s about figuring out the pieces behind Crochet.

With the lefty locked into the No. 1 spot — and Opening Day starts for years to come — the Red Sox find themselves with a deep stable of (mostly young) pitchers who will, barring trades, enter camp in the mix. The only lock at this point is Brayan Bello, who after the best season of his big league career, profiles as the top internal option behind Crochet who is under control for next year. Lucas Giolito, who stabilized the group for most of the year, is likely to hit free agency through a complicated mutual option, though he’s a qualifying offer candidate. More on that in a minute.

Behind Crochet and Bello, the Red Sox find themselves deeper than ever when it comes to rotation options — and especially, young ones. Now, it’s about identifying who is poised to contribute and fill out the group. In Kutter Crawford, Hunter Dobbins, Connelly Early, Richard Fitts, Kyle Harrison, Patrick Sandoval, Payton Tolle and even swingman Cooper Criswell, Boston has eight candidates who have varying levels of experience and upside. Even with Tanner Houck set to miss most (if not all) of 2026 after undergoing Tommy John surgery in August, Boston has its fair share of depth.

There are Early and Tolle, the tantalizing left-handed prospects who each showed flashes (especially in Early’s case) late in 2025. There are Crawford and Sandoval, veterans who are coming off missing the entire season due to injury, and Dobbins, who was a bright spot early and should be ready for Opening Day after tearing his ACL in July. Harrison, the main prize from the Rafael Devers trade, is still 24, and Fitts will be 26 in the spring. It’s fair to assume a couple of things. One, the Red Sox can dangle young arms in trade talks. Two, spring training will be a bloodbath when it comes to the rotation competition. And three, it’s fair to assume one or two guys on the list will emerge as real forces.

In previous seasons, the Red Sox were tasked with adding bodies to their staff in order to amass depth from the outside during the offseason. This time, that depth is built-in. Breslow isn’t going to add for the sake of adding. He’s going to try to raise the ceiling of his rotation group.

WHAT’S COMING FROM THE MINORS?

This past season saw the Red Sox debuts of Dobbins, Early, Harrison and Tolle, who all spent time in Triple-A. None of those pitchers are a finished product and all of them represent the improved depth in the upper levels of the minors. It’ll be very beneficial for the Red Sox to have pitchers with major league experience at Triple-A throughout the season and that’s a lock to be the case considering how many arms there are in that group.

Tolle and Early were on track for 2026 debuts before a series of injuries forced the Red Sox to call them up as they pushed toward the postseason. They’re not the only exciting pitchers in the system, though. Perhaps the most electric right-handed arm in the organization is Luis Perales, who is impressing with triple-digit velocity in the Arizona Fall League and will be in the mix next season. David Sandlin had a good season as a starter before a bullpen experiment gone awry. Shane Drohan returned with a strong showing in Triple-A. The cupboard is not bare, even with Brandon Clarke, Kyson Witherspoon, Marcus Phillips, Anthony Eyanson and others further away. The aggressive path taken with Tolle last year suggests Breslow is not afraid to fast-track a capable arm in an effort to win games.

WHICH MOVES MIGHT THE RED SOX MAKE?

With Crochet and Bello locked in and the group of (in some order) Early, Sandoval, Crawford, Tolle, Dobbins, Harrison, Fitts and Criswell all in the mix, the Red Sox could enter spring training having made no additions and likely field a competitive rotation. The 2025 season, though, revealed not just the need for a massive amount of depth but also the importance of quality rotation options. For most of the year, the Red Sox had a pretty good chance when either Crochet, Bello or Giolito pitched. Things were different when they didn’t.

One of the most striking needs for the Red Sox as they look to push from contender to World Series contender is finding a running mate for Crochet. Bello is a good pitcher who can be dominant, but true No. 2 starters don’t get lifted after 28 pitches in a win-and-move-on playoff game. The Red Sox are likely approaching this winter hoping to add a No. 2, install Bello as the No. 3 and figure out the rest with the options listed above. They’ll have plenty of ways to get that done, too.

Reigning Cy Young winner Tarik Skubal is going to headline a deep class of trade candidates, though it’s possible Detroit’s reported interest in listening on him is a negotiating tactic before extension talks really heat up. Everyone knows Minnesota’s Joe Ryan is the apple of Breslow’s eye. Milwaukee’s Freddy Peralta, Washington’s MacKenzie Gore (hello, Paul Toboni), Cincinnati’s Hunter Greene and Andrew Abbott, Pittsburgh’s Mitch Keller and Miami’s Sandy Alcantara all might be moved. The Red Sox can obviously put together an attractive package involving a major league outfielder, a young pitcher with big league experience and a prospect or two. It’ll just come down to a team finding that price to be right if Breslow goes the trade route. That price will be determined by a combination of talent and contractual control.

The always-risky free agent market is an option, too, and like he did last year with flirtations with Blake Snell, Max Fried and others, Breslow will be sure to be involved. Framber Valdez, Dylan Cease, Ranger Suárez and Michael King are the top options with many others, including Zac Gallen, Nick Martinez, Chris Bassitt, Merrill Kelly and Shane Bieber, available as well. It’s hard to imagine the Red Sox looking for a deal like the one they gave Walker Buehler a year ago. Any pursuits on the open market should be for a true upgrade — think someone markedly better than Bello.

A wild card in all of this is Giolito, who enters free agency in a strange scenario. He has a $19 million mutual option (that comes with a $1.5 million buyout) that is almost always a lock to be declined by one side, meaning he’s effectively a free agent. A strong, healthy finish would have positioned Giolito for a multi-year deal on the open market. Instead, elbow soreness — with no structural damage — ended his year before the postseason and will give teams pause entering the season.

The qualifying offer — and a Giolito acceptance of that $22.025 million deal for next year — is possible. So, too, is a different type of deal that keeps him in Boston, especially if the Red Sox feel comfortable with medicals other teams aren’t yet privy to. Giolito has loved his time in Boston and the Red Sox consider him one of their best leaders. A relative bargain caused by the elbow issue might create a pathway to a deal. A reunion there certainly wouldn’t rule out a rotation upgrade elsewhere — and it would make it more palatable for Breslow to trade someone like, say, Dobbins or Harrison.

FINAL ANALYSIS / PREDICTION:

The Red Sox enter the winter with a true ace in Crochet, a mid-rotation guy in Bello — and a bunch of darts that may or may not hit bullseyes in the future. It’ll be much easier for the Red Sox to figure out that puzzle with a true No. 2 in place.

The prediction here is that for the second straight winter, Breslow does some high-end shopping when it comes to the rotation. A Giolito departure makes free agency more likely. A Giolito reunion makes the trade market more attractive. The Red Sox need someone like Ryan, Cease, King or Gore to pitch Game 2 of a postseason series next fall. Breslow knows that and will likely act accordingly.

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