Boston Red Sox chief baseball officer Craig Breslow has made plenty of questionable decisions in recent months. One of those decisions was sending left-hander Kyle Harrison to the Milwaukee Brewers in a six-player trade that landed third baseman Caleb Durbin with the Red Sox.
Harrison has thrived for the Brewers in 2026, while Durbin has struggled immensely for the most part. Durbin's actually caught fire of late -- he's hitting .308 with four homers in his last 15 games. But the memory of his 2026 season up until recently is still painful, as Durbin was one of the worst starting-level players in Major League Baseball through the first 50 games or so. Even now, Durbin is still hitting just .215 with a .630 OPS.
Durbin would have never been targeted by Breslow had the CBO not utterly fumbled the Alex Bregman negotiations and found himself in need of a third baseman. And while Durbin's rookie season in 2025 was awesome in Milwaukee, his downturn with the Red Sox has been a vivid symbol of everything that's wrong with Breslow and the Red Sox's development of young players.
Every player that joins the Red Sox seems to get worse, and every player that leaves the Red Sox seems to thrive elsewhere. There are some exceptions, of course. Willson Contreras has thrived in Boston. Meanwhile, David Hamilton, who was sent to Milwaukee in the Durbin deal, hasn't vastly improved in a Brewers uniform.
The Red Sox are acquiring Caleb Durbin from the Brewers, per @JeffPassan
— B/R Walk-Off (@BRWalkoff) February 9, 2026
Kyle Harrison, David Hamilton and Shane Drohan head to Milwaukee in the deal pic.twitter.com/Btb1Gxf1qW
David Hamilton surprisingly hasn't turned into the best version of himself since leaving the Red Sox!
Hamilton's .236 batting average this season is a tad north of his career .226 figure, but it's lower than his .248 figure for Boston in 2024, a season in which Hamilton also finished with 17 home runs and showed what kind of impact he can have at the MLB level (he's hit six homers for Milwaukee so far this season).
What's interesting about Hamilton is that Milwaukee specifically targeted him during the Harrison-Durbin deal. According to a new piece from The Athletic's Ken Rosenthal, Milwaukee "expanded the package" of that deal so that they could snag Hamilton, sending Andruw Monasterio and other assets to the Red Sox in addition to Durbin.
Hamilton hasn't been a disappointment in Milwaukee, but it's almost surprising that he isn't having the best season of his career, given how so many other ex-Red Sox are killing it right now (seemingly, all of them). If you had to point to one positive from this trade for the Red Sox, it would be that Hamilton hasn't improved dramatically in Milwaukee. If Durbin continues this current hot streak, the deal will begin to trend in slightly different direction altogether.
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