November is here, and with the colder weather comes a hibernation of sorts on the baseball diamond. But the lack of major league competition doesn’t mean a lack of action.
The Boston Red Sox, along with 29 other clubs that didn’t get to lift the Commissioner’s Trophy will be looking to reset and get better. Unlike most of those teams, the Sox have been named in the top 5 of ESPN’s ‘way too early power rankings’ for the 2026 season.
Craig Breslow has talked a lot in the last few weeks about pitching acquisitions, saying: “Every team gets better if you can bring in a starter or develop a starting pitcher that could pitch at Garret Crochet’s level, right?” This was seemingly a throwaway line tossed out by Breslow at the end of season press conference.
To be clear, Crochet is a Cy Young Award finalist, so to suggest that your team will improve by adding a pitcher of that caliber isn’t a hot take. But, follow me here: What if it was!?
What if, the front office were to play a bit of fantasy baseball and develop a two-ace stable with a cast of other crucial supporting pieces. It’s not out of the question, with outlets already naming the Sox as a frontrunner to scoop up Tarik Skubal in another winter blockbuster. A devastating Crochet-Skubal axis as 1a and 1b starters would be a dream scenario, and here’s how the rest of a punishing pitching corps would come together to round out that vision.
Dream Red Sox starting rotation for the 2026 season
Garrett Crochet
Crochet's position at the top of the rotation is a given after his performance in 2025. The lefty posted a 2.59 ERA, 1.028 WHIP and an MLB-best 25 strikeouts over 205.1 innings pitched. He's Boston's clear ace — a clearer one than it's had in quite some time — and another top-tier starter following him in the rotation could only improve his already-dangerous game.
Tarik Skubal
Jen McCaffrey of The Athletic noted in a Red Sox mailbag piece that Skubal could command as much as $400 million in free agency next winter. To land him, the Sox might have to move an even greater haul of prospects than the package that brought Crochet to Boston. She suggests a potential deal could include Franklin Arias, the team’s top prospect, or Jhostynxon Garcia, Jarren Duran, and one or both of Connelly Early and Payton Tolle.
To make matters worse, Skubal is yet another Scott Boras client, making a mid-season extension less likely. Boston might consider a deal here if it’s ready to open the purse and let the dollars fly.
More importantly, trading for Skubal while also augmenting the lineup elsewhere (like resigning Alex Bregman or bringing in Pete Alonso) might just deliver an environment Skubal would be happy to stick around for.
Brayan Bello
Boston’s consummate No.3, Bello is a returning piece that took some big strides forward in 2025. He shaved more than a full point off his 2024 ERA, bringing it down to 3.35, and saw his WHIP diminish as well. Bello isn’t going anywhere, and fits nicely into a steady third slot behind two killers on the bump.
Zac Gallen
Dylan Cease is the flashier name heading to free agency, but Gallen is a far greater innings eater, tossing nearly 200 frames in '25. Boston pitched to the second best bullpen ERA in the majors but ranked somewhat poorly in attritional counting stats like batters faced. Adding Gallen offers a different look.
Unlike Bello’s sinker-heavy delivery and Crochet’s sinker-sweeper mix, Gallen confounds hitters with a curveball that drops almost 18 inches at times. Add in his changeup and Gallen is good for the 86th percentile in offspeed run value. He is not a ground ball pitcher, like the three previous names, breaking up the pattern. Gallen is also notable at managing runners on the basepaths.
Gallen’s 4.83 ERA this year is ugly, but it’s more than a point above his career average and he keeps runners off the basepaths fairly well with a career average WHIP of 1.16 (1.26 in 2025).
The next man up
Tanner Houck is out of the 2026 conversation after requiring Tommy John surgery this winter. Kutter Crawford, Richard Fitts, and perhaps even guys like Jordan Hicks will have an opportunity to prove themselves. If either of the young guys who have bubbled up into Boston’s roster survive a thus-far hypothetical trade for Skubal, they’ll also be strong contenders to turn the rotation back over. Arms like Kyle Harrison and David Sandlin are also potential candidates to prove themselves. Luis Perales has also reached triple-digits with his fastball, introducing another solid option that might spoil Alex Cora with riches.
Such strength at the top of the lineup offers another benefit. The fifth man isn’t likely to have nearly as much pressure on his shoulders. Taking the heat off the bottom of the rotation will make for an easier transition for the young guys, priming the pump for one or more of these exciting youth arms to eventually take over the mantle when the time comes.