Garrett Crochet did a lot of heavy lifting at the top of the Boston Red Sox's rotation in 2025, and chief baseball officer Craig Breslow hopes to net the Cy Young Award finalist some backup for the upcoming season.
The Red Sox have been linked to many of the arms available this offseason on both the free agent and trade markets, and there's still reason to believe they hope top upgrade their rotation beyond Sonny Gray. Their offensive needs and hesitance to commit to long-term deals for free agents have most people expecting the Sox to trade for their No. 2 starter. There's no shortage of excellent options on the trade market, but some of them suit Boston's needs better than others.
Freddy Peralta could be an ideal trade target for the Sox, and the Milwaukee Brewers often trade their best players before they reach free agency, as they don't extend many of their homegrown stars. Peralta could be on the trade block this winter and MLB insider Jim Bowden of The Athletic predicts that the Red Sox could land him in exchange for two pitching prospects, Payton Tolle and Anthony Eyanson (subscription required).
Breslow's revamped pitching infrastructure and focus on pitchers in the last two MLB Drafts has given Boston a deep pool of pitching prospects to trade from. The Red Sox have more than enough young pitching to trade Tolle and Eyanson to Milwaukee, and in that event, signing Peralta long-term must immediately become a priority.
The Red Sox should only trade for a Freddy Peralta this winter if they can extend him
The Sox saw Tolle's skillset in his first year of professional baseball, when he debuted in High-A and finished his year in the major leagues during a playoff push. He projects as a front of the rotation arm at his best, and he's already improved so much in the Red Sox organization that he could open the 2026 season on the roster. He posted a 3.04 ERA, a 0.99 WHIP, 133 strikeouts and 23 walks over 91.2 innings across three levels of the minor leagues last season.
The Red Sox selected Eyanson in the third round of the 2025 MLB Draft and consider him a steal. The 21-year-old starred for LSU last season with a 3.25 ERA, 152 strikeouts and 36 walks over 108 innings. He hasn't made his professional debut yet, but SoxProspects projects him as a middle rotation starter, and his 12.7 strikeouts per nine innings in college speak for themselves.
Both Tolle and Eyanson could factor in as rotation staples for the Red Sox in the near future, and if they're going to sacrifice both of them in a trade, they should make that return a fixture of the team. Peralta has been a top pitcher in the National League for years, and he's consistent. He's posted a 3.59 ERA over his eight seasons with the Brewers with 2025 being his best one yet — he clocked a 2.70 ERA, 1.075 WHIP, 204 strikeouts and 66 walks over 176.2 frames.
Extending him won't come cheap, but the clock is officially ticking on Crochet and Roman Anthony's contracts. The Red Sox are in a great position to win for years to come with the young core they've established, they just have to build around it. Peralta would be an ideal complement to Crochet in the rotation for the foreseeable future, and if Boston trades for him (or any other No. 2 starter) this winter, it must ensure that happens with a contract extension.