Red Sox Trade David Hamilton to Brewers
Boston sends David Hamilton, Kyle Harrison, and Shane Drohan to Milwaukee for three players.
Updated on Oct. 26, 2026 in Baseball
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The Boston Red Sox have completed a trade sending David Hamilton, Kyle Harrison, and Shane Drohan to the Milwaukee Brewers. In exchange, the Red Sox acquired Caleb Durbin, Andruw Monasterio, and Anthony Seigler.
Why it matters
The Brewers targeted David Hamilton for his electric speed and defensive versatility, while the Red Sox sought to bolster their roster with Caleb Durbin’s righthanded swing and third base defensive ability.
The incoming group of Durbin, Monasterio, and Seigler produced a combined 5.5 bWAR in 2026, significantly outperforming the 2.8 bWAR generated by the departing trio of Hamilton, Harrison, and Drohan.
The players
David Hamilton
He is a professional baseball player known for his speed and defensive versatility who recorded 33 stolen bases in 2024.
Caleb Durbin
He is a professional infielder valued for his righthanded hitting and defensive capabilities at third base.
Boston Red Sox
This is a professional Major League Baseball team based in Boston that plays its home games at Fenway Park.
Milwaukee Brewers
This is a professional Major League Baseball team based in Milwaukee that competes in the National League.
The details
David Hamilton appeared in 204 games for Boston, starting 104 and recording 33 stolen bases in 2024 followed by 30 in 2026. Caleb Durbin, who joins the Red Sox, previously underwent surgery on his left pinky finger in October 2026 following a dislocation.
Timeline
December 1, 2021: David Hamilton was initially acquired by Boston from Milwaukee.
2023-2025: David Hamilton played for the Boston Red Sox.
June 24, 2026: Caleb Durbin dislocated his left pinky finger.
October 2026: Caleb Durbin underwent surgery on his finger.
Season Trajectory
This transaction mirrors the 2021 trade of David Hamilton from the Milwaukee Brewers to the Boston Red Sox by effectively returning the player to his original organization. The move signals a shift in roster strategy for both clubs as they adjust their lineups for the upcoming season.
The acquisition of Caleb Durbin adds a new righthanded defensive option to the Red Sox infield rotation. Meanwhile, the departure of David Hamilton removes a base-stealing specialist from the roster who led the National League with 13 sacrifices in 2026.
The takeaway
Teams often prioritize defensive versatility and specific swing mechanics when restructuring rosters through multi-player trades. Evaluating the combined bWAR of incoming versus outgoing talent provides a clear metric for assessing the immediate impact of such deals.
Further reading
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Source note: This article includes information reported by The Boston Globe.
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