The Los Angeles Dodgers' pursuit of three straight World Series titles ended Thursday night as they were swept in the National League Championship Series by the Milwaukee Brewers. As you look at the pennant-winning Brewers’ roster, former Boston Red Sox players are scattered throughout. 

Here’s what you need to know about the former Red Sox as they pursue the first World Series title in Brewers history: 

The former Red Sox utility man provided a crucial insurance run in the ninth inning of Thursday night’s series-clinching victory, launching a 402-foot solo home run off Los Angeles’ All-Star closer Edwin Diaz, extending the Milwaukee lead to two at 6-4. 

Acquired by Milwaukee as part of the trade that sent third baseman Caleb Durbin to Boston, the 29-year-old utility man appeared in 121 games for Milwaukee in the regular season, hitting .245/.314/.336/.650. In four postseason games, Hamilton is hitting .455/.500/.727/1.227 with one home run, two RBI, and three stolen bases. 

Initially an eighth-round selection of Milwaukee in the 2019 MLB Draft, the utility infielder was traded to Boston in December 2021 alongside prospect Alex Binelas and center fielder Jackie Bradley Jr. in exchange for outfielder Hunter Renfroe. After making his major league debut in June 2023, Hamilton appeared in 204 games for the Red Sox across three seasons, hitting .222/.283/.359/.642. 

A fifth-round pick of the Red Sox in the 2020 MLB Draft, the left-handed pitcher spent the first four seasons of his professional career in the Red Sox organization before being selected by the White Sox in the 2023 Rule 5 Draft. After injuries prevented him from appearing in a game for Chicago, Drohan was returned to Boston. 

Drohan was sent to Milwaukee with Hamilton and starter Kyle Harrison in the Durbin trade. In 33 regular-season appearances for the Brewers, the 29-year-old left-hander posted a 4.19 ERA. 

In his lone appearance this postseason, Drohan has allowed one run in one inning of work, walking two and striking out one. 

After being acquired from the Dodgers ahead of the 2025 trade deadline, May struggled mightily during his brief stint in a Red Sox uniform. In six appearances for Boston, the then-27-year-old right-hander posted a 5.20 ERA before an elbow injury ended his season ahead of the playoffs. 

May signed a one-year, $12.5 million deal with the St. Louis Cardinals in free agency, posting a 4.38 ERA in 21 starts. He was dealt to Milwaukee ahead of the trade deadline in exchange for a pair of prospects. In his first 10 starts in a Brewers uniform, he struggled to a 5.65 ERA. 

The 29-year-old’s struggles have followed him into the postseason, where he’s allowed five earned runs on seven hits in seven innings across three appearances. 

Finally, there’s Harrison, who was the centerpiece in the June 2025 trade that sent All-Star designated hitter Rafael Devers to the San Francisco Giants. The 25-year-old spent much of his time in the Red Sox organization in Triple-A with the Worcester Red Sox, making only three appearances with Boston. In those three appearances, Harrison allowed four earned runs on 12 hits across 12 innings, striking out 5 and walking one. 

After signing All-Star starter Ranger Suarez in free agency and the emergence of Payton Tolle and Connelly Early as major-league-caliber starters, Harrison became expendable for the Red Sox, leading them to flip him as the centerpiece in the trade to acquire Durbin. 

Harrison looked like one of baseball's best young starters at the start of the year, posting a 2.79 ERA in his first 21 starts. However, he limped to the finish line, posting a 16.05 ERA in his final seven appearances, and his struggles led Milwaukee manager Pat Murphy to move him into a bullpen role. 

Despite being on the roster for both the NLDS and NLCS, the 25-year-old has not yet appeared in a game. 

The Brewers will await the winner of the American League Championship Series between the Tampa Bay Rays and the Cleveland Guardians. The World Series begins Friday, Oct. 23. 

Looking for more on the Red Sox needs heading into the offseason? Zach Coe and David Azer are back on the 'Entering Kenmore' Podcast discussing how close Boston is to winning a World Series, whether the 2026 season was a success, and whether fans should have faith in Craig Breslow's ability to build a World Series contender. Check it out wherever you get your podcasts, or in the YouTube player below: