Dustin May won the World Series with the Los Angeles Dodgers in 2020, but his experience with the Milwaukee Brewers in 2026 carried even greater personal meaning.

May’s career and life changed dramatically in 2024, when he suffered a life-threatening esophageal tear after choking on a piece of lettuce. Baseball immediately became secondary to his survival and recovery.

During an interview with MLB Network, May explained that the 2026 World Series against the Tampa Bay Rays meant more because of everything he had endured during the previous two years.

At one point, he did not know whether he would ever play again, making his opportunity to experience that moment with Milwaukee especially meaningful.

“For me, it means more to be here in this moment today knowing two years ago, looking back where I was, I wasn’t really sure if I was ever going to play again,” May said. “So being able to be here in this moment, it truly means the world to me.”

Los Angeles used the injury as justification to trade May to the Boston Red Sox. He later joined the St. Louis Cardinals, who traded him and JoJo Romero to Milwaukee before this year’s deadline.

May has since declined his $20 million mutual option with the Brewers and entered free agency.

The right-hander went 7-9 with a 4.70 ERA and 1.32 WHIP in 145.2 innings over 31 starts with the Cardinals and Brewers in 2026.

May started 10 games for Milwaukee but completed fewer than four innings in six of them. His Brewers tenure began encouragingly before his performance gradually moved in the wrong direction.

He went 2-2 with a 5.65 ERA and 1.42 WHIP in 36.2 innings over those 10 starts.

May also struggled during the postseason, posting a 5.73 ERA and 1.18 WHIP in 11 innings over five appearances (two starts).

Those results will complicate his free agency, but they do not erase the determination required to return from such a frightening medical emergency.

May faced uncertainty extending far beyond the usual concerns surrounding a pitcher’s career and still worked his way back into an MLB rotation.

His experience as both a starter and reliever could provide options for an interested team.

May might no longer receive an immediate guarantee that he will remain in the rotation, but he has already demonstrated a willingness to contribute in different assignments during the postseason.

The next organization that signs him will need to determine which role gives him the best chance to recover his effectiveness. A place in the back of a rotation could offer regularity, while a bullpen assignment might allow him to work in shorter appearances.

May also brings experience from multiple organizations and two World Series titles. He understands the demands surrounding a contender and the adjustments required after changing teams during a season.

His 2026 performance was uneven, particularly after arriving in Milwaukee. However, reaching the World Series after once questioning whether he would play again gave the season meaning beyond his results.

Free agency presents another uncertain step, but May has already overcome circumstances far more serious than an undefined pitching role.