Red Sox's Andruw Monasterio Proving Brewers Blockbuster Was a Sneaky Win

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Sometime around the end of May, we as baseball fans were collectively acting as though the Boston Red Sox's offseason trade with the Milwaukee Brewers was an abject disaster.
The results didn't look promising. Lefty Kyle Harrison was having a tremendous breakout campaign in Milwaukee, while the centerpiece of the trade from Boston's side, Caleb Durbin, was one of the worst hitters in Major League Baseball for the first two months of the season.
Durbin's turnaround and Harrison's injury were already starting to shift the public perception. But over the past few weeks, it's also become abundantly clear that the Red Sox landed more than one impact player in the deal. On Wednesday night, when a lot of fans were sleeping, Andruw Monasterio cemented himself in 2026 Red Sox lore.
Monasterio's game-winning home run puts stamp on huge stretch

Monasterio, who has become the surprise everyday shortstop in Boston after a series of injuries, gave the Red Sox a much-needed boost against the lowly Athletics. He launched a two-run blast to give the Red Sox a 4-2 lead in the top of the 10th inning of Wednesday's game, and that would be the final as Greg Weissert somehow slammed the door in the bottom half.
Monasterio has heated up at the perfect time. Since July 1, he's got a 1.118 OPS and three home runs. The Red Sox have gone 13-4 in games he's played this month. And against all odds, he's the obvious choice to play shortstop on any given night at the moment, with the only real alternative being Nick Sogard.
Overall, Monasterio now sits with a .260 batting average, .780 OPS/119 OPS+, six home runs, and 1.0 bWAR in 67 games on the year.
Add in the fact that the acquisition of Monasterio basically offset the Red Sox dumping David Hamilton to the Brewers, and it's becoming clearer by the day that Boston got the better end of the deal, at least for the 2026 season.
Are there more trades to win at the upcoming Monday deadline? Monasterio and the Red Sox just have to keep plugging away and hope the front office rewards their turnaround efforts.

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