Two years ago, Dustin May openly questioned whether he would ever throw a baseball in the major leagues again. A grueling sequence of physical setbacks—beginning with a flexor tendon injury that necessitated Tommy John surgery, followed by a torn esophagus and a subsequent elbow injury—threatened to cut short his professional career. Those medical challenges derailed his 2024 season and severely limited his playing time the following year, casting deep shadows over his future as a pitcher.
Now, the 29-year-old right-hander finds himself on baseball’s biggest stage, preparing for a World Series appearance with the Milwaukee Brewers. Reflecting on his unlikely return during an appearance on Foul Territory, May expressed profound gratitude for reaching this milestone. Looking back at the uncertainty of the prior two years, he acknowledged that he never knew if he would play again, making his current presence with the team feel especially fortunate.
May’s winding path to October began after pitching 104 innings during the first half of the 2025 season with the Los Angeles Dodgers. Even though he was not part of the active roster for their final title run, Dodgers manager Dave Roberts honored May’s contributions on May 1 by presenting him with a 2025 World Series championship ring prior to a game against the St. Louis Cardinals.
Following a trade to the Boston Red Sox, May subsequently joined the Cardinals on a one-year, $12.5 million contract. He made 21 starts for St. Louis, posting a 5-7 record and a 4.38 ERA. That performance drew the interest of the Milwaukee Brewers, who acquired him ahead of the August 3 trade deadline.
Production dipped following the move to Milwaukee. May recorded a 2-2 mark with a 5.65 ERA across 10 starts for the Brewers. He finished the regular season with a 7-9 overall record, a 4.70 ERA, and 144 strikeouts across 145.2 innings.
Despite the late-season adjustments, the Brewers utilized May out of the bullpen during their postseason run. He pitched three innings against the San Diego Padres, allowing two earned runs with three strikeouts, resulting in a 6.43 ERA across three playoff outings.
The National League Championship Series appearance on October 15 presented a tougher test. Los Angeles Dodgers star Shohei Ohtani connected on a pitch down and in for a home run that accounted for all three of May’s earned runs in the outing, though May recovered to throw a clean third inning and record a single in the fourth. The Brewers ultimately swept the series 4-0 against the Dodgers, capturing the franchise’s first pennant since 1982.
With a pitching staff heavily reliant on bullpen games, May’s ability to absorb multi-inning workloads has provided valuable depth for Milwaukee. As the World Series opens at American Family Field with Jacob Misiorowski taking the mound against Tampa Bay Rays starter Nick Martinez—followed by Logan Henderson in Game 2 and Robert Gasser in Game 3—May remains a key option for high-leverage relief or potential bullpen games as the Brewers pursue their first championship.
