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Red Sox-Brewers Trade Suddenly Looks Different After Months of Criticism

Just taking notice...
Jun 8, 2026; St. Petersburg, Florida, USA;  Boston Red Sox third baseman Caleb Durbin (5) mishandles a ground ball in the sixth inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Jonathan Dyer-Imagn Images
Jun 8, 2026; St. Petersburg, Florida, USA; Boston Red Sox third baseman Caleb Durbin (5) mishandles a ground ball in the sixth inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Jonathan Dyer-Imagn Images | Jonathan Dyer-Imagn Images

It's been a rough season in the public eye for Boston Red Sox chief baseball officer Craig Breslow, and the move that has earned him perhaps his worst criticism has been a February trade with the Milwaukee Brewers.

On Feb. 9, Breslow shipped left-handed pitcher Kyle Harrison, alongside fellow lefty Shane Drohan and infielder David Hamilton, to the Midwest. In exchange, Boston got its replacement for Alex Bregman at third base in Caleb Durbin, infielders Anthony Seigler and Andruw Monasterio, plus a competitive balance pick at the end of the first round in the upcoming draft.

For the majority of the season, Harrison looked incredible, while Durbin was one of the worst hitters in Major League Baseball. On the whole, the results are still skewed in Milwaukee's favor. But this week has been a reminder that we shouldn't consider it a foregone conclusion that this deal will haunt Boston for years.

After Harrison's blow-up, Durbin shines

Kyle Harrison
Milwaukee Brewers pitcher Kyle Harrison (52) throws during the first inning of their game against the San Francisco Giants Tuesday, June 2, 2026 at American Family Field in Milwaukee, Wisconsin. | Mark Hoffman/Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

In his worst start by far as a Brewer, Harrison surrendered eight earned runs in only 2 1/3 innings on Monday against the Athletics. That game, which was played at a Triple-A stadium in Las Vegas, featured some truly absurd home runs, finished in a 15-14 Brewers win.

Meanwhile, after failing to hit a home run against a real pitcher all season (he had one against a position player), Durbin hit two blasts against Tampa Bay Rays pitching on Wednesday during Boston's 7-5 loss.

Durbin was sporting a .984 OPS with eight extra-base hits and nine RBIs in 12 games since he spent half a week on the bench and worked with a new hitting coach who was suggested to him by teammate Carlos Narváez.

Of course, one bad outing for Harrison doesn't mean he's destined to struggle for the rest of the season. Even after he got shelled, he maintained a 2.72 ERA to go with his 7-1 record. He may still very well make the National League All-Star team.

This is baseball, after all. A great week can undo a few bad ones, and a terrible start on the mound can make a season look a lot worse than it really has been. Bur Harrison, for all the improvement he'd shown in Milwaukee after some noticeable adjustments like raising his arm angle and trusting his new change-up grip, was still probably due for some regression.

Durbin had some bad BABIP luck too, though it doesn't help to constantly be hitting the ball on the ground. He was due to come around to some degree at some point, and it looks like that's happening.

Now, the question is to what degree he can continue building on that modicum of success.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@moreviewsmedia.com