The Boston Red Sox are expected to be one of the most active teams in the trade market this offseason. Reports indicate they are targeting Chicago White Sox ace Garrett Crochet. With one of the top farm systems in baseball, proven young Major League talent, and a proactive front office, the Red Sox are open to trading any player to improve their team.
Although the Red Sox have several talented prospects, all of their top prospects are position players, and they urgently need to bolster their starting pitching. While Crochet could be a good option, concerns about his durability and his limited experience as a starting pitcher (only one full season) make him a risky acquisition.
One team the Red Sox should target for a young, controllable starting pitcher is the Pittsburgh Pirates.
A potential trade proposal could see the Red Sox send shortstop prospect Marcelo Mayer (MLB’s No. 7 prospect), outfielder Braden Montgomery (No. 54), and outfielder Wilyer Abreu to the Pirates for starting pitcher Jared Jones.
At just 23 years old, Jared Jones is among the top young pitchers in baseball. In his rookie season with the Pirates in 2024, he started 22 games, recording a 6-8 record, a 4.14 ERA, and 132 strikeouts in 121 2/3 innings. Jones relies heavily on his fastball, which averages 97.3 mph, and his devastating slider, which posted a 37.3% whiff rate. Despite a strong start to the year, Jones struggled in the second half. However, his youth, potential, and five years of team control could make him available for the right offer.
The Pirates have depth in their minor league system, with other pitching prospects like Bubba Chandler (MLB No. 15), Braxton Ashcraft (No. 85), and Thomas Harrington (No. 91), meaning they may be open to trading Jones if it brings back a significant package.
For the Red Sox, who saw improvements in their rotation during 2024 but lack a clear No. 1 starter, Jones could slot in as a No. 2 behind Tanner Houck. With further development, Jones could become a future All-Star.
The Pirates, who are building around National League Rookie of the Year Paul Skenes at the top of their rotation, might be willing to move Jones due to his second-half struggles and the presence of strong pitching prospects behind him. A trade to the Red Sox could provide them with a package that would be hard for other teams to match.
From the Pirates’ perspective, their offense struggled in 2024, ranking near the bottom in several key categories. They need to surround Skenes with a stronger offense, and one area of need is shortstop. With Oneil Cruz moving to center field, the Pirates could use a top-tier shortstop prospect. Mayer, ranked as the second-best shortstop prospect in baseball, would immediately be a candidate for the Pirates’ starting shortstop job.
Along with Mayer, outfielder Wilyer Abreu, who impressed during his 2024 rookie season with a .253/.322/.459 slash line and 15 home runs, would provide the Pirates with a solid right fielder and potential middle-of-the-order hitter.
While Mayer and Abreu are highly valuable, the Pirates would likely seek an additional piece. Outfield prospect Braden Montgomery, or other players such as starting pitcher Kutter Crawford, infielder David Hamilton, or lower-level pitching prospects like David Sandlin and Richard Fitts, could be included to complete the trade.