David Hamilton is back with the Milwaukee Brewers, and the trade has already turned into a useful October move. The 29-year-old returned from the Boston Red Sox in a deal that sent Hamilton, left-hander Kyle Harrison and minor league left-hander Shane Drohan to Milwaukee for Caleb Durbin, Andruw Monasterio and Anthony Seigler.
That matters now because Hamilton was in the Brewers' lineup long before Game 3 of the World Series on Monday night, not waiting on the margins. Going into that game, he was 6 for 17 with a double, a homer, three RBIs and three stolen bases, and he had started five of Milwaukee's first 10 postseason games. For a player who spent 2023-25 with Boston and never quite settled in as an everyday regular there, it was a sharp change in role and timing.
Hamilton was acquired by the Red Sox from Milwaukee on Dec. 1, 2021, then spent three seasons trying to carve out a steady place in Boston. He appeared in 204 games for the Red Sox, but played the entire game only 110 times, a sign of how often he was used as a utility infielder at second base and shortstop rather than as a locked-in starter. Even so, he still flashed what made him attractive in the first place. In 2024, he led all major league rookies with 33 stolen bases, and he had five games with three hits during his time with Boston. One of his best moments there came on May 13, 2025, when he hit a game-tying two-run homer in the eighth inning in Detroit.
The move back to Milwaukee has given him a different kind of chance. Brewers manager Pat Murphy said Hamilton might be a full-time player, pointing to his electric speed, improving bat-to-ball skills and defensive ability on seven positions on the diamond. Murphy also said the Brewers knew they were getting a good player back. Hamilton has settled in as the third baseman, which gives Milwaukee a more direct path to using him every day than Boston ever found. What comes next is whether that October role becomes a longer one, or whether this trade ends up being remembered as the moment Milwaukee finally found the fit Boston never quite did.
