The Boston Red Sox experienced a notable front-office departure late last season when they lost one of their most respected young executives to a division rival in baseball operations. In September, the Washington Nationals officially hired Paul Toboni away from Boston, naming him their new president of baseball operations. Toboni had been viewed inside the Red Sox organization as a rising executive with a sharp eye for talent evaluation and organizational planning, and his exit marked a significant change behind the scenes for the franchise.
Fast forward just three months, and Toboni found himself doing business with his former employer — and former boss — in a way that is rarely seen across Major League Baseball. Toboni and Red Sox chief baseball officer Craig Breslow orchestrated a direct, one-for-one exchange of pitching prospects, a move that was quietly completed but drew significant attention among league evaluators once it became public. The trade was confirmed through the Red Sox’ official transactions page on MLB.com and quickly sparked analysis from scouts and analysts around the sport.
According to respected minor-league analyst Keith Law of The Athletic, the trade represented an uncommon “win-win” scenario for both organizations. Rather than one team clearly getting the better end of the deal, Law viewed the transaction as a case where each club acquired a pitcher who fits its immediate and long-term needs. For Boston, the incoming piece is left-handed pitcher Jake Bennett, while Washington received right-hander Luis Perales, a former top-five prospect in the Red Sox system.
Bennett arrives in Boston with an impressive physical profile and a skill set that the Red Sox believe can help them in the near future. The 25-year-old southpaw stands at 6-foot-6 and weighs approximately 234 pounds, giving him the kind of imposing frame that modern pitching development staffs covet. Originally selected by the Nationals in the second round of the 2022 MLB Draft out of the University of Oklahoma, Bennett had been ranked as Washington’s No. 11 overall prospect by MLB Pipeline prior to the trade. Upon joining the Red Sox organization, he immediately slots in as the club’s No. 7 prospect.
His arrival further strengthens a growing pattern within Boston’s pitching pipeline — an unusual concentration of arms with roots in Oklahoma. Bennett joins fellow Oklahoma native Payton Tolle, who is currently ranked as the No. 2 overall prospect in the Red Sox system and is widely regarded as their top pitching prospect. The similarities between the two are hard to ignore: both are left-handers, both boast towering frames, and both came through the collegiate ranks in the Sooner State.
In fact, Bennett and Tolle are not alone. Three of the Red Sox’ top four pitching prospects hail from Oklahoma, an almost comical coincidence that underscores how heavily the organization has leaned into that talent pool in recent drafts and acquisitions. Right-handed pitcher David Sandlin, ranked No. 8 overall in the system, is also an Oklahoma native. Sandlin was drafted in 2022 as well, though much later — in the 11th round — by the Kansas City Royals. Boston acquired Sandlin in 2024 when Breslow dealt reliever John Schneider to Kansas City, a move that quietly paid dividends for the Red Sox’s pitching depth.
The Oklahoma connections do not end there. The Red Sox have continued to add arms from the state in recent drafts. In 2024, the team selected right-hander Barrett Morgan in the 11th round. A year earlier, in the final draft overseen by former chief baseball officer Chaim Bloom, Boston used a 16th-round pick on left-handed reliever Isaac Stebens out of Oklahoma State. Between draft selections and trades, Oklahoma has become an unlikely but important pipeline for Boston’s pitching development.
Bennett himself has strong ties to several of those names. He and Sandlin were teammates at Oklahoma, sharing a rotation and competing together at the collegiate level before entering professional baseball in the same draft class. That familiarity could ease Bennett’s transition into a new organization, particularly one that already values the type of pitcher he has developed into.
From a performance standpoint, Bennett is not viewed as a power arm in the traditional sense, but evaluators believe his skill set is extremely playable at the major-league level. Law noted that Bennett profiles as a classic control-oriented starter — a pitcher who thrives by filling up the strike zone, limiting free passes, and forcing hitters to earn their way on base. That trait has been consistent throughout his career.
“He throws strikes and always has,” Law wrote in his analysis of the trade. The numbers back that assessment up. During the 2025 season, Bennett walked just 6.4 percent of the batters he faced. In 2023, before his season was cut short by injury, his walk rate sat at 6.2 percent. Going back even further, during his draft year at Oklahoma in 2022, he issued walks to just 4.5 percent of opposing hitters. Across every level, command has been the foundation of his profile.
Law also believes Bennett could be knocking on the door of the majors sooner rather than later. In his view, the left-hander “should pitch in the majors this year,” with the most likely scenario being a midseason call-up when the Red Sox need rotation depth. Given Boston’s recent struggles to maintain consistent health among its starters, Bennett could realistically see meaningful innings in a big-league role if he continues progressing as expected.
To acquire Bennett, Boston parted with Luis Perales, a pitcher who has long intrigued scouts due to his raw arm strength. Perales was originally signed by the Red Sox in 2019 during the tenure of former chief baseball officer Dave Dombrowski, who is now running baseball operations for the Philadelphia Phillies. Hailing from Guacara, Venezuela, Perales joined the organization for a modest $75,000 signing bonus, a relatively small investment that quickly looked like a bargain.
As Perales climbed through the minor leagues, his electric fastball became his calling card. The right-hander has touched triple digits, with radar gun readings reportedly reaching as high as 101 mph. That kind of velocity is rare and tantalizing, even if it comes with questions about durability and role. While Perales had been ranked as high as No. 5 in Boston’s system, his future had become increasingly cloudy following a major setback.
Perales underwent Tommy John surgery in 2024, a procedure that derailed his development and placed his immediate outlook in doubt. Though many pitchers successfully return from the surgery, it often takes time for command and velocity to fully return. Law suggested that Washington views Perales primarily as a potential bullpen piece rather than a starter, a role that could allow his elite velocity to play up while reducing the physical strain on his arm.
Interestingly, Bennett has also undergone Tommy John surgery, having the procedure performed in 2023. That shared medical history may have helped both teams feel more comfortable parting with their respective pitchers. In Boston’s case, the Red Sox appear to value Bennett’s command, size, and starter profile enough to accept the injury risk, particularly given his progress since returning to the mound.
Bennett’s acquisition also fits into a broader trend under Breslow’s leadership. Over the past month, the Red Sox have aggressively added large-bodied pitchers to their system, prioritizing size, durability, and upside. Bennett is the third pitcher standing at least 6-foot-5 that the team has brought in during December alone.
Earlier this month, on December 4, Boston acquired right-hander Johan Oviedo from the Pittsburgh Pirates. Oviedo stands 6-foot-6 and weighs a massive 275 pounds, making him one of the most physically imposing pitchers in the organization. Shortly thereafter, the Red Sox completed a deal with the Oakland Athletics to acquire their Rule 5 Draft selection, right-hander Ryan Watson, who measures 6-foot-5 and weighs 225 pounds.
Taken together, these moves paint a clear picture of the Red Sox’s evolving pitching philosophy. Under Breslow, the organization appears committed to building a pipeline of tall, durable arms who can handle innings, pound the strike zone, and provide flexibility between starting and relief roles. Bennett fits squarely within that vision.
While the trade may not have generated headlines across the national media, its implications could be felt sooner than expected. If Bennett reaches the majors this season and provides stability to a rotation in need of reliable innings, the deal could quickly be viewed as a savvy piece of business by Boston’s front office. Meanwhile, Washington gains a high-upside arm in Perales who could eventually impact their bullpen in meaningful ways.
In the end, the rare prospect-for-prospect swap underscores how relationships, familiarity, and organizational philosophy can shape decision-making across Major League Baseball. For Toboni and Breslow, it was a professional reunion rooted in mutual trust — and one that may ultimately benefit both franchises for years to come.
