Boston Red Sox
After landing Garrett Crochet in a trade last offseason, the Red Sox still have one of the stronger farm systems in baseball to possibly make a deal for a top pitcher.
It’s evident that the Red Sox need some help at the top of their rotation, which is part of the reason why one insider believes they’ll be in the mix for some of the top pitchers who might be available this offseason.
In a column listing the top 10 MLB players most likely to be traded this offseason, The Athletic‘s Jim Bowden listed the Red Sox as a fit for the five top pitchers on the list — Tigers LHP Tarik Skubal, Brewers RHP Freddy Peralta, Reds RHP Hunter Greene, Nationals LHP MacKenzie Gore, and Marlins RHP Sandy Alcantara.
Bowden cited the Red Sox’ “deep farm system” as part of the reason why they might be able to land one of those pitchers. They’d certainly need to tap into their farm system in order to acquire Skubal, who seems likely to be named AL Cy Young for a second straight season soon.
However, there isn’t much precedent of a team trading a back-to-back Cy Young winner. The Blue Jays’ trade of Roger Clemens to the Yankees in 1999 is the only such instance of that happening, with New York giving up All-Star David Wells and supplementary pieces for the then-36-year-old Clemens.
Considering Skubal’s age (he’ll turn 29 in November) and other recent trades involving star pitchers, you’d have to imagine the Tigers would get more than what the Blue Jays did for Clemens in 1999. Just last offseason, the Red Sox gave up two top-100 prospects, including a top-50 prospect in Kyle Teel, for Garrett Crochet despite only being a starting pitcher for one season.
Entering the offseason, the Red Sox have four players ranked in MLB Pipeline’s top-100 prospects list (Payton Tolle, Kyson Witherspoon, Jhostynxon Garcia, Franklin Arias). On top of that, the Red Sox have a couple of other recently graduated top prospects (Marcelo Mayer, Kristian Campbell) who could be made available and pitcher Connelly Early, who has had a brief stint of success in the majors.
It should be noted that Skubal is entering the final year of team control. There’s a $250 million gap between what Skubal is asking for and what the Tigers have offered, according to the New York Post‘s Jon Heyman, as some insiders have speculated that he could be the first pitcher to receive a $400 million deal.
Beyond Skubal, Peralta is the only other pitcher on that list entering the final year of team control. The Brewers All-Star went 17-6 with a 2.70 ERA this past season.
As for Gore, Bowden noted that the Nationals’ decision to hire Red Sox assistant general manager Paul Toboni to be their next general manager could make Boston a natural fit for the lefty.
“He’s so familiar with Boston’s prospect cabinet that I’m sure he’d find a strong return even if he can’t land the team’s very best prospects in a trade,” Bowden wrote.
Gore might not have the results the other pitchers on Bowden’s list do, but there is upside there. He turns 27 in February and has logged a sub-4.00 FIP the last two years despite having a 4.17 ERA this past season. He’s also under team control until 2028.
Greene might be the most far-fetched option of the five as the 26-year-old has three more seasons of team control left and has posted a sub-3.00 ERA in each of the last two seasons. That helped the Reds make the playoffs for the first time in over a decade this past season.
Finally, Alcantara was a rumored Red Sox target ahead of the trade deadline in July. The Red Sox offered the Marlins multiple packages that included Tolle, Garcia, and Arias as the headlining prospects for the righty, WEEI’s Rob Bradford reported at the time.
After missing the entire 2024 season due to Tommy John surgery, Alcanara struggled in 2025 (11-12, 5.36 ERA). However, the 30-year-old won the NL Cy Young in 2022 and posted a 3.70 ERA over the last two months of the season.
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