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Rollercoaster evaluation of Brewers' Kyle Harrison trade with Red Sox gains new chapter

There's a long way to go before a clear winner of this offseason trade is crowned.
ByTyler Koerth
Sep 6, 2026; Cincinnati, Ohio, USA;  Milwaukee Brewers pitcher Kyle Harrison (52) throws against the Cincinnati Reds in the first inning at Great American Ball Park. Mandatory Credit: Aaron Doster-Imagn Images
Sep 6, 2026; Cincinnati, Ohio, USA; Milwaukee Brewers pitcher Kyle Harrison (52) throws against the Cincinnati Reds in the first inning at Great American Ball Park. Mandatory Credit: Aaron Doster-Imagn Images | IMAGN IMAGES via Reuters Connect

If the early-season trade between the Milwaukee Brewers and Boston Red Sox involving LHP Kyle Harrison, LHP Shane Drohan, 2B David Hamilton, 3B Caleb Durbin, SS Andruw Monasterio, and 2B Anthony Seigler had a rolling chart tracking which team was “winning” the deal, it would include several drastic swings in each team's favor. The six-player swap has gone from a win-lose, to a win-win, to a lose-lose in a matter of five months.

Milwaukee was the clear victor through the first two months of the season, with Harrison posting a 1.57 ERA through his first 11 starts, Hamilton receiving the first extended opportunity at third base, and Drohan emerging as a key, versatile piece to the Brewers’ pitching staff. At the same time, Durbin was among the worst hitters in baseball while finding his footing with his new squad.

However, in June, Durbin began to heat up at the plate for Boston, which coincided with the Red Sox turning their season around. In July, Boston went on an improbable 15-game winning streak en route to posting a remarkable 21-4 record that month. During that same stretch, Monasterio stepped in at shortstop for an injured Trevor Story and took full advantage of the opportunity, posting a 1.044 OPS over 19 games.

August, however, proved to be a difficult month for Harrison, Durbin, and Monasterio, changing the tone surrounding some of the biggest pieces involved in the deal. Hamilton also endured a pair of costly throwing mistakes at home plate, with one costing Milwaukee a game against the Mets in extra innings and another allowing a pair of Reds runners to score over Labor Day Weekend.

Taken together, those developments have written yet another chapter in the rollercoaster that has been the ongoing evaluation of this trade.

Recent struggles have once again shifted the narrative surrounding the Brewers and Red Sox' offseason trade

During the month of August, Harrison posted a 5.01 ERA, leaving Milwaukee with questions about whether he can be trusted with the ball in the early stages of a postseason matchup. As a result, the Brewers have expressed the idea of experimenting with Harrison in the bullpen in September. Additionally, Hamilton has seen his playing time decrease as Joey Ortiz continues to swing a hot bat and provide stronger defense at the hot corner.

On the East Coast, Durbin has posted just a .626 OPS over the past 30 days, with only one home run. Meanwhile, Monasterio has recently settled back into a utility infield role after Story was activated and Mona posted a .578 OPS across 27 games in August.

With Seigler back in the minor leagues after spending June through August with the Red Sox, Drohan has emerged as the only truly consistent piece of the deal. While his 4.09 ERA may not jump off the page, he's been a steady force on the Brewers' pitching staff. Drohan’s 114.1 innings are the second-most on the Milwaukee’s pitching staff this season, making his contributions quite valuable for a team relying on a young group of arms.

All that said, there is still no clear winner in the Brewers-Red Sox trade. What initially looked like a major win for Milwaukee shifted to a win-win in June and July, but August brought struggles from key pieces on both sides. With neither team currently getting consistent production from the players they acquired, the "winner" of the trade remains up in the air.

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