The Boston Red Sox may be on an eight-year World Series drought, the longest since they won in 2004, but there are a handful of former Red Sox still competing in the Fall Classic this season.
The Milwaukee Brewers and Tampa Bay Rays will face off for a matchup of two teams to never win a World Series, each carrying a few former Sox. These six players could win a ring in the next week while the Red Sox watch from home.
6 former Red Sox who could win a ring for the 2026 World Series
Kyle Harrison
Kyle Harrison will be best known by Red Sox fans as the main player the Red Sox targeted in the Rafael Devers trade and failed to capitalize on. He spent most of his Red Sox tenure in Worcester, making a few very solid starts at the end of the season. The Red Sox sent him to the Brewers late last offseason in the deal that brought Caleb Durbin, Andruw Monasterio, and Anthony Seigler to Boston.
Early in the season, it looked like the Brewers fleeced the Red Sox, as the lefty was dealing and looking like a dark-horse Cy Young candidate. At the end of May, he had made 11 starts and had a 1.57 ERA. Before he hit the injured list in July, he still had a 3.01 ERA in 18 starts. His second half was abysmal, though, with a 7.31 ERA in 11 appearances. He was relegated to the bullpen, where he still struggled. He has yet to pitch in the playoffs.
Shane Drohan
Shane Drohan was the least known player sent by Boston in that same trade. He had yet to make his MLB debut, but the Sox did protect him from the Rule 5 draft earlier that offseason. With Milwaukee, he made 19 starts with a 5.01 ERA, but he became elite once moved to the bullpen.
In 14 relief appearances spanning 30 2/3 innings, the lefty had a 1.47 ERA. He held opponents to a .193 batting average and .520 OPS. He had almost as much fWAR (0.9) in relief as he did as a starter (1.1) in 1/3 of the innings. He has only pitched one inning so far in the playoffs.
David Hamilton
David Hamilton was the lone position player sent to Milwaukee in the Durbin-Harrison move. The speedster played a similar role for the Brewers as he did in Boston. He spent most of the year on the Brewers roster, save a three-week stint on the IL. The Brewers helped his plate approach, with him setting the lowest strikeout rate of his career and highest walk rate, but besides that, he was mostly the same player. He's only played four games in the playoffs (of a possible eight), and he's hitting .455 with one home run and three stolen bases.
Dustin May
Just as he was in Boston a year ago, Dustin May was a deadline pickup for the Brewers, who needed extra arms in their starting rotation. He signed with St. Louis in the offseason and seemed to find his Dodgers form; after two brutal starts to begin the season, he had a 2.54 ERA from April 10 to June 15. He started to regress from there, posting a 6.26 ERA in his final seven Cardinals starts before he was traded.
He couldn't regain his form after joining the Brewers. He had a 5.65 ERA in 10 appearances, mostly being an opener in his final three starts as he didn't go more than three innings. So far in the playoffs, he's pitched seven innings and allowed five runs.
Super happy for Cam Booser. Dude was just thankful to get a shot in the big leagues with the Sox at the age of 31. Now, he’s getting huge outs in a clincher game and heading to the World Series. pic.twitter.com/1MxKNLI8HS
— Steve Perrault (@Steve_Perrault) October 20, 2026
Cam Booser
Cam Booser's was an amazing feel-good story for the 2024 Red Sox. He dealt with multiple severe injuries in high school, college and the minors, including being hit by a car and breaking bones in his back. He was suspended for marijuana use and also dealt with alcoholism and depression, causing him to step away from baseball at the age of 25 for four seasons. After retiring, getting himself sober, and finding his passion for the game again, Booser made a comeback and eventually made his MLB debut with the Sox in 2024.
The lefty was dealt to the White Sox after the 2024 season and he had a rough 2025. He signed with the Rays for the 2026 season and became an elite reliever. Booser pitched 41 innings with a 1.98 ERA. He had just 45 strikeouts and just six walks this season. He's made six appearances in the postseason so far and has yet to allow a run.
Steven Matz
Steven Matz was the other Red Sox 2025 deadline pickup, and he is also pitching in the World Series. The lefty signed with Tampa over the offseason, initially as a starter, but he moved back to the bullpen in early June. He struggled through most of this season, having an ERA over 5.00 as both a starter and reliever. He made one appearance so far in the playoffs, pitching two innings without allowing a baserunner.
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