Dustin May won the World Series with the Los Angeles Dodgers in 2020 before securing another title with the Milwaukee Brewers in 2026.

May declined his $20 million mutual option with Milwaukee after the season 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 for the St. Louis Cardinals and Brewers in 2026.

Milwaukee used May as a starter 10 times, but he completed fewer than four innings in six of those appearances. His time with the Brewers began encouragingly before his results gradually declined.

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

His difficulties continued during the postseason. May posted a 5.73 ERA and 1.18 WHIP in 11 innings over five appearances (two starts).

May will not return to Milwaukee, creating another opening within the rotation. Right-hander Shane Bieber could replace him and give the Brewers an intriguing option with considerable upside.

When healthy, Bieber has demonstrated that he can rank among the best pitchers in baseball. He won the 2020 American League Cy Young Award with the then-Cleveland Indians, who are now known as the Cleveland Guardians.

Bieber owns a career 3.32 ERA and 1.13 WHIP in 939 innings over 154 appearances (152 starts) during nine seasons.

He went 5-2 with a 4.37 ERA and 1.42 WHIP in 55.2 innings over 11 starts for the Toronto Blue Jays in 2026.

Injuries have disrupted Bieber’s career during the past several seasons, which should prevent his price from becoming excessive. Milwaukee could consequently obtain a low-cost starter with ace upside and an opportunity to rebuild his value.

Bieber would bring more than name recognition to the Brewers. He understands how to prepare for a starting assignment, adjust during games and navigate a lineup multiple times when his body allows him to work deep into outings.

His previous success also proves that his ceiling extends far beyond that of an ordinary rotation depth addition.

Milwaukee would not be signing an untested pitcher and hoping for an unexpected breakthrough. The organization would be betting that an accomplished starter can rediscover enough of his previous form to become an important contributor.

That possibility fits the Brewers’ approach. Milwaukee has repeatedly helped pitchers refine their assignments, maximize what remains effective and succeed without requiring the organization to make an enormous financial commitment.

Bieber would still carry substantial risk because his recent availability cannot be ignored. The Brewers would need additional rotation depth rather than relying on him to replace May by himself.

However, a short-term agreement could benefit both sides.

Bieber would receive an opportunity to restore his reputation with the reigning World Series champions, while Milwaukee would add an experienced starter capable of delivering far more value than his likely cost suggests.