Last year, in December, Red Sox chief baseball officer Craig Breslow made a blockbuster trade that shaped Boston’s season, setting the club up for a what turned out to be its first entry into the playoffs since 2021, and only second since 2018.
But to land the former Chicago White Sox ace Garrett Crochet, Breslow was forced to give up not just one but four of the Red Sox organization’s top prospects â including catcher Kyle Teel who at the time was Boston’s No. 4 ranked prospect. Breslow also gave up outfielder Braden Montgomery, whom he had selected with Boston’s first round draft pick, No. 12 overall, just a few months earlier.
Montgomery quickly moved up the ladder to become the No. 1 prospect in the White Sox system, No. 35 overall in baseball.
Trade With Nationals in Works?
Teel got the call for his big league debut on June 6, and Chase Meidroth â another top prospect traded for Crochet â made his debut even quicker, on April 11. Both stuck on the White Sox MLB roster for the rest of the season.
The fourth prospect traded for Crochet, righty pitcher Wikelman González, was the Red Sox’ No. 7 prospect at the time of the trade. González made his big league debut on June 20, ultimately appearing in 16 games for the White Sox.
The Red Sox gave up a lot to get Crochet, but the deal clearly benefited both organizations. Now, Breslow may get the chance to do it again, after his own assistant general manger Paul Toboni was hired by the Washington Nationals as their new GM.
Toboni proceeded to hire two of his own AGMs from the Red Sox, and pledged to turn the Washington organization into a âscouting and player development monster,â much like the Red Sox have become.
MacKenzie Gore May be on Trade Block
Toboni also finds himself with an All-Star pitcher to trade in 26-year-old MacKenzie Gore, who still has two years to go before hitting free agency and is projected by MLB Trade Rumors to receive an affordable $4.7 million salary next season.
Toboni’s declaration that he plans to develop a “player development monster,” according to MLB Trade Rumors analyst Steve Adams, “doesnât exactly sound like someone whose focus is on fast-tracking a return to contention, and moving Gore could provide a serious jolt to a farm system thatâs still in the bottom third of MLB despite being in year four of a rebuild.”
If Breslow were to deal from what Bleacher Report, in its final 2025 farm system rankings, rated as the 12th-best minor league prospect pool in the game, he most likely would not need to surrender four top prospects. Gore does not pitch at the same level of dominance as Crochet, who also came with two years of team control â but quickly signed a six-year, $170 million extension with Boston.
A Prospect Duo to Get Gore to Boston
Trading with Washington for Gore would also mean that the Red Sox could keep their big league roster intact, with Toboni’s priority with the Nationals as building for the future. But which prospects could Breslow deal?
If Crochet required four prospects, including one from the Red Sox’ top-five, Gore would most likely take only two.
Would a combination of Red Sox No. 3 prospect â power-hitting outfielder Jhostynxon “The Password” Garcia â and rookie league pitcher and No. 12 prospect Marcus Philips, a 21-year-old whose fastball reaches 100 mph, and who was the Red Sox second first-round pick in 2025 (33rd overall), be enough to sell Toboni on parting with Gore?
Red Sox, and Nationals, fans will likely find out sometime between December 7 and 11, when baseball’s annual winter meetings â generally the busiest time for offseason trades â take place in Orlando, Florida.
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