While most baseball pundits know better than to question the Milwaukee Brewers organization, especially when it comes to acquiring starting pitching, their decision on Monday morning to trade NL Rookie of the Year candidate Caleb Durbin to the Boston Red Sox came as a shock to the system. The Brewers had the best record in MLB's regular season in 2025. This offseason, they've subtracted, trading ace Freddy Peralta to the New York Mets and now Durbin to Boston.
There is always a method to Milwaukee's madness, but I can't claim to know what NL Executive of the Year Matt Arnold is up to, here. As for the Red Sox, they've been searching for a third baseman ever since Alex Bregman signed with the Chicago Cubs. In Durbin, they add one in a big way, and at a relatively minor cost.
MLB trade grades: Red Sox acquire Caleb Durbin from Brewers
Brewers trade grade: C
The Brewers must have a whole ton of faith in Harrison, a former top prospect in the San Francisco Giants system who was once part of the Rafael Devers trade. Harrison has a 4.39 ERA in three MLB seasons. He only made two starts with the Red Sox. The other two throw-ins, both 27-years-old, could help the Brewers roster as early as this season. Hamilton doesn't offer much at the plate, as he had a .590 OPS this season. Drohan, a 27-year-old pitcher who spent most of last season in Triple-A and A-ball, doesn't improve this return package all that much.
I don't have much more to add on the Brewers end. This makes no sense to me.
Red Sox trade grade: B+
Durbin is a legitimate infielder the Red Sox can build around. While he is no Devers or Bregman at this point in his career, Durbin was the centerpiece of this trade, and a former Yankee at that. New York traded Durbin to the Brewers as part of the Devin Williams deal. Durbin had a .721 OPS and 101 OPS+ in his rookie season, also offering plus defense at second and third base. Red Sox fans will love him for that reason, and he adds another key member to their young core. Durbin also finished third in NL Rookie of the Year voting just last season.
Monasterio, should he make the Red Sox big-league roster, provides more infield depth for a team that could definitely use it. Most of Boston's roster strength is in the outfield. Seigler, meanwhile, was a former first-round pick by the Yankees back in 2018. He hasn't amounted to much in the big leagues, but a change of scenery could help matters.
Why did the Red Sox trade for Caleb Durbin?
Durbin is a significant upgrade over Hamilton, who would've received significant playing time if the season started tomorrow. Durbin offers a similar amount of speed – he had 18 stolen bases in 2025, and holds the Arizona Fall League record with 29 steals – and is an elite contact bat. The 25-year-old struck out under 10 percent of the time, and was in the 98th percentile of all MLB hitters in that department.
Most importantly, Durbin buys the Red Sox time to figure out exactly what they want to do in their infield. Boston still has an outfield surplus, so they could trade from a position of strength to add even more infield talent if they need it. Durbin is flexible, and can play either second base or third depending on Alex Cora's preference.
Whether it be filling in for Romy Gonzalez at second, or giving Marcelo Mayer more time to develop at third, the Red Sox know exactly what they're getting from Durbin at the plate and in the field. He has a high floor, and is the type of player the Red Sox can rely on come October.