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Former Brewers' everyday third baseman continues season turnaround with walk-off in game of the year

The once-lopsided swap is starting to look like a win-win.
Aug 4, 2026; Boston, Massachusetts, USA; Boston Red Sox third baseman Caleb Durbin (5) hits a grand slam against the Chicago White Sox in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images
Aug 4, 2026; Boston, Massachusetts, USA; Boston Red Sox third baseman Caleb Durbin (5) hits a grand slam against the Chicago White Sox in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | IMAGN IMAGES via Reuters Connect

Earlier this season, the Milwaukee Brewers looked like the clear winner of their offseason trade with the Boston Red Sox -- the deal that brought Kyle Harrison, Shane Drohan, and David Hamilton to Milwaukee. In the time since the trade, Harrison has cemented himself as the No. 2 option alongside Jacob Misiorowski in the Brewers' rotation, Drohan has served as the unsung Swiss Army knife of the pitching staff, and Hamilton has seen regular playing time at shortstop and third base.

Meanwhile, Boston acquired Caleb Durbin, Andruw Monasterio, and Anthony Seigler in return. Durbin was easily the headliner in the Red Sox' return package, but he got off to an awfully slow start, entering June with a batting average of just .186. His struggles, combined with Boston's 25-33 record at the time, were certainly not what fans or President of Baseball Operations Craig Breslow had in mind when the trade went down during the offseason.

However, shortly before the calendar flipped to June, Durbin started to heat up. From May 28 through June 5, he put together an eight-game hitting streak and hasn't looked back since. Over his last 59 games, Durbin has a .313/.377/.526 slash line with 10 home runs, 13 doubles, and 35 runs batted in. This turnaround has raised his season batting average to .251 and has coincided with the Red Sox winning more games. Boston currently sits at 63-51 and would be a Wild Card team if the postseason started today.

Along the way, Durbin has collected a few clutch hits as well. On July 20, amidst a lengthy Red Sox winning streak, he capped off a come-from-behind effort by hitting a go-ahead home run in the eighth inning against the Baltimore Orioles to extend Boston's winning streak, which eventually ended at 15 games.

More recently, Durbin delivered a walk-off single against the Chicago White Sox in one of the wildest games of the season. The 13-inning marathon featured Boston erasing a four-run deficit, with the Red Sox pulling even five separate times before finally taking their first lead of the night on the final hit of the game.

Caleb Durbin capped off another Boston Red Sox come from behind victory with a walk-off single

In the high-scoring 12-11 thriller, Durbin did far more than just deliver the game-winning hit. He reached base four times, going 3-for-6 with a double and a walk, setting the tone for Boston's relentless comeback. After contributing throughout the night, Durbin capped his standout performance by lining the walk-off single off Erick Fedde, another former Brewer, to complete the victory.

Durbin's walk-off single came just days after he hit the first Grand Slam of his major league career, which also came against the White Sox. Needless to say, Red Sox fans are now thrilled to have him in Boston, and his prolonged surge at the plate has begun to make the offseason trade look far more balanced.

That said, the Brewers have still received excellent production from the players they acquired in the deal. Harrison returned from the injured list looking just as sharp as he did during the first half of the season, and Drohan, a regular in the starting rotation over the last two months, has a 3.48 ERA on the season. As both clubs continue to benefit from the trade, it increasingly looks like a deal that could ultimately prove to be a win-win for both organizations.

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