The Red Sox completed a rare prospect-for-prospect trade with the Nationals last month, sending right-hander Luis Perales to Washington in exchange for left-hander Jake Bennett.
Beyond the player swap, the deal marked a notable first: it was the first trade between Red Sox chief baseball officer Craig Breslow and new Nationals front office leader Paul Toboni, who spent more than a decade in Boston’s organization before departing for Washington.
Bennett, 25, fits the exact pitching profile Breslow has prioritized since taking over Boston’s baseball operations. Standing 6-foot-6, Bennett aligns with a clear organizational trend—Breslow has selected 28 pitchers who are 6-foot-4 or taller since reshaping the Red Sox pitching pipeline, signaling a strong preference for size and physicality on the mound.
That philosophy has already yielded results, most notably in Red Sox top pitching prospect Payton Tolle, who’s ranked No. 1 by SoxProspects. Tolle stands 6-foot-6 and weighs 250 pounds, and once he got into Boston’s pitching program, the southpaw’s velocity jumped dramatically. At TCU, Tolle’s fastball sat around 91 mph; last season, it averaged 95 and touched 99.
Tolle’s leap serves as a blueprint for how the Red Sox believe they can elevate pitchers who fit their mold—and Bennett checks many of the same boxes.
One of Bennett’s standout traits is elite extension.
Extension measures how far from the rubber a pitcher releases the ball; the farther the release point, the more uncomfortable the at-bat becomes for hitters. While pitching in the Arizona Fall League, Bennett averaged 7.02 feet of extension, ranking in the 93rd percentile among Major League pitchers in 2025.
To put that into perspective, Phillies left-hander