The trade between the Boston Red Sox and the Milwaukee Brewers didn’t look like a bombshell. No superstars. No record-breaking contract. But the closer you look, the more it seems like a trade that could shape the depth of both sides’ rosters—and leave more questions than answers.

Caleb Durbin, 25, is the centerpiece for Boston. A player labeled “scrappy,” small in stature, solid third-base defense, and accustomed to being underestimated. Durbin finished his rookie season with slash lines of .256/.334/.387—only about 5% above the league average. On the surface, that’s a solid record. But the advanced data is much colder: low exit velocity, low barrel rate, and big question marks about his ability to consistently score damage.
So why did the Red Sox pick him?

The answer lies in how Durbin survives. He doesn’t hit the ball hard—he hits the right kind of ball. Last season, Durbin made a significant adjustment: he pulled the fly ball more to optimize his power for his physique. The results came in the second half of the season with seven home runs in 234 plate appearances. The price was a sharp drop in OBP, highlighting the challenge Durbin faced in Boston: how to maintain pressure with the fly ball without sacrificing his base presence.

Along with Durbin were Andruw Monasterio—a versatile player, hitting .270/.319/.437 in limited time, playing across the infield and even the left field; Anthony Seigler—a solid defensive player but with questionable batsmanship; and a 2026 Competitive Balance Round B draft pick. Boston was clearly buying versatility and options, not a guaranteed offensive promise.

In return, the Brewers acquired Kyle Harrison—a former top-25 prospect left-winger in MLB. Harrison, 24, hasn’t exploded as expected since being acquired in the Rafael Devers trade. He only made three MLB appearances for the Red Sox with a 3.00 ERA in 12 innings, otherwise being relegated to the minors. But if there’s any team that makes people believe it’s “not too late,” it’s Milwaukee—a team with a history of turning young, underdeveloped pitchers into valuable assets.

The Brewers also acquired Shane Drohan—a 27-year-old pitcher whose K-rate has increased significantly in the minors but is “old” for the Triple-A; and David Hamilton—a good defensive infielder but a lackluster batsman. This is a package deal serving the restructuring process after Milwaukee parted ways with ace Freddy Peralta earlier.
Notably, with Boston, this deal continues to dismantle pieces from the Devers deal. Jordan Hicks left after struggling; now Harrison. The message is clear: the Red Sox aren’t bound by old decisions. They’re ready to pivot quickly if they feel the risk-reward ratio is no longer a good fit.

For Durbin, Boston is both a favorable and a challenging environment. Favorable because the team is ready to optimize its approach—pull fly ball, disciplined ball handling, leveraging the Fenway. Challenging because if BABIP turns his back, the “empty average” will quickly become apparent. Durbin needs to prove that the adjustments made in the latter half of last season were sustainable, not haphazard.
Ultimately, this is a trade of belief in development. The Red Sox believe they can hone a weak batting player into a versatile contributor. The Brewers believe they can “unlock” a pitcher who was once highly rated. Who is right won’t be decided in April—but in the quiet adjustments mid-season.
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