Red Sox’ Jake Bennett trade reflects Craig Breslow’s pitching vision for Boston

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 Cristopher Sánchez and Giants righty Sean Hjelle are among big leaguers who generate seven feet of extension or more—Sánchez stands 6-foot-6, while Hjelle is 6-foot-11.

Bennett hasn’t reached the big leagues yet, so direct comparisons may be premature, but Sánchez offers an intriguing similarity. The Phillies lefty thrives with a sinking fastball and a devastating changeup—two pitches that also feature prominently in Bennett’s five-pitch arsenal.

Bennett works with a fastball that sits 92–95 mph, complemented by a changeup, cutter, slider, and curveball. His heater is currently his best offering, and he’s shown an ability to use it effectively at the top of the zone. His changeup features late fade and has proven to be a legitimate swing-and-miss pitch both in and out of the strike zone.

A second-round pick in 2022, Bennett underwent Tommy John surgery in 2023 before returning to the mound this past summer. Across three levels, he posted a 2.27 ERA and 1.08 WHIP over 19 appearances (18 starts). He also logged extra innings in the Arizona Fall League, where he finished with a 4.50 ERA across 20 frames.

Another factor that appealed to Boston was Bennett’s command. He walked just six percent of batters faced last season, a stark contrast to Perales, who issued walks at an 18 percent clip. Despite Perales’ raw talent, his erratic control played a role in Boston’s decision to move him.

Breslow believes Bennett’s blend of strikes and whiffs points toward a future in a Major League rotation.

“We believe we are getting a Major League-caliber starting pitcher,” Breslow said after the trade. “The combination of whiff and strikes is unique, and we started to see the performance catch up in the AFL.”

SoxProspects currently projects Bennett as more of a back-end rotation starter, though that evaluation could evolve as he continues his development within Boston’s system.

Outside of his fastball, Bennett’s changeup is viewed as one of his best weapons—drawing parallels to fellow left-hander Connelly Early. 

In the AFL, Bennett’s changeup generated a 40.3 percent whiff rate. That pitch usage aligns well with Worcester’s philosophy; the WooSox threw the fifth-highest percentage of changeups among Triple-A teams last season (12.4 percent).

While Bennett is expected to open the year in Portland, his development could accelerate quickly once he reaches Polar Park.

Baseball America describes Bennett as a “no-doubt starter with a good chance to settle in as a No. 4 type in a rotation.” 

While he’s not a high-octane strikeout arm, his 21.5 percent strikeout rate paired with a 6.4 percent walk rate produced a strong 15.2 percent K-BB%. He also generated ground balls at a 48.4 percent clip while throwing strikes nearly 65 percent of the time.

“We feel like Bennett is a high-probability starter that excels in some things that are hard to teach,” Breslow said. “Fastball playability driven by above-average extension and strike-throwing ability.”

Bennett’s arrival also gives Boston additional flexibility. With a surplus of left-handed pitching in the system, Breslow now has the option to deal from organizational depth. One name that could become expendable in trade discussions is Kyle Harrison, whom the Red Sox acquired in the Rafael Devers deal.

Boston remains active in the market for infield help, and Astros third baseman Isaac Paredes has emerged as a player of interest. One league source said the Red Sox and Astros have held recent discussions, with Harrison among the names to watch in any potential trade.

Additional options on Boston’s radar include Cubs second baseman Nico Hoerner, Cardinals infielder Brendan Donovan, and free agent third baseman Eugenio Suárez, whose thunderous power would add a different dimension to the middle of the lineup.

Already on the 40-man roster, Bennett may not spend long in Double-A if he performs as expected. The trade represents another calculated bet by Breslow on his pitching philosophy—one that could pay dividends sooner rather than later if Bennett continues to build on his core strengths.