Four Former Boston Red Sox Players Win World Series with Brewers

For the first time in franchise history, the Milwaukee Brewers are World Series champions after defeating the Tampa Bay Rays 4-1 in Wednesday night’s Game 5. After an offseason deal between Milwaukee and the Boston Red Sox, the World Series champions' roster is littered with former Red Sox players. 

Here’s what you need to know about the newest World Series champs. 

The former Red Sox utility man became a postseason hero for Milwaukee in the title-winning run. Hamilton provided a crucial insurance run with a solo home run in the series-clinching Game 4 of the NLCS, a game-tying solo shot in Game 4 of the World Series, and an RBI single that extended Milwaukee's lead to two in the top of the fifth in Wednesday’s win. 

Milwaukee acquired the 29-year-old utility man as part of the trade that sent third baseman Caleb Durbin to Boston; he hit .333/.357/.593/.950 with two home runs, one double, and six RBI in nine postseason games. Hamilton appeared in 121 regular-season games for Milwaukee, hitting .245/.314/.336/.650. 

Initially selected by Milwaukee in the eighth round of the 2019 MLB Draft, the utility infielder was traded to Boston in December 2021 alongside prospect Alex Binelas and center fielder Jackie Bradley Jr. 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. 

Another piece of the offseason deal that sent Durbin to Boston, Drohan appeared in one World Series game, taking the loss in the Rays’ extra-innings Game 4 win. The 27-year-old left-hander appeared in only two postseason games, allowing two earned runs on five hits over 1.0+ innings. 

In 33 regular-season appearances for the Brewers, the 29-year-old left-hander posted a 4.19 ERA. 

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 kept him from playing for Chicago, Drohan was returned to Boston before being traded to Milwaukee. 

After being acquired from the Dodgers ahead of the 2025 trade deadline, May struggled during his brief stint in a Red Sox uniform. In six appearances for Boston, the then-28-year-old right-hander posted a 5.20 ERA before an elbow injury ended his season ahead of the playoffs. After signing a one-year deal with the St. Louis Cardinals in free agency, May was traded to Milwaukee at the trade deadline in exchange for a pair of prospects. 

In two World Series appearances, the 29-year-old allowed two earned runs on four hits, striking out three. May made five appearances in the postseason, posting a 5.73 ERA in 11 innings. With the World Series win, May became the second active player with four World Series rings, joining former Red Sox outfielder Mookie Betts. He had three with the Dodgers.

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 left-hander was flipped as the centerpiece in the Durbin trade after just nine months in the Red Sox organization. 

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 postseason roster for all three series Milwaukee played, Harrison did not appear in the playoffs. 

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.