Dustin May Sweepstakes Includes 4, Including Brewers Bitter Rival

One former member of the Milwaukee Brewers is already generating significant interest in free agency after his stint with the organization.

On Wednesday night, MLB Network's Jon Morosi reported that former Brewers starter Dustin May has interest from the Chicago Cubs, Chicago White Sox, San Diego Padres and the Houston Astros, at the very least.

"Free agent RHP Dustin May is drawing interest from a broad group of teams that includes the Cubs, White Sox, Padres and Astros, sources say," Morosi wrote. "Of note, new Astros GM Randy Flores was in the Cardinals front office when they signed May last offseason. May, 29, is one of the youngest starters on the market this winter."

The Former Brewers Hurler Is Available

Oct 24, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch against the Tampa Bay Rays during the fifth inning in game two of the 2026 World Series at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

May presents an intriguing case in free agency. His numbers weren't great as a member of the Brewers. May had a 5.65 ERA in 10 starts down the stretch and then followed up with a 5.73 ERA in five appearances for the Brewers in the playoffs. At the end of the day, he gave the Brewers the depth arm that they needed and he was a positive addition overall. But numbers weren't great, so it will be interesting to see how teams view him in the open market.

The biggest thing going for him is the fact that he's still just 29 years old. As a member of the St. Louis Cardinals in 2026, he had a 4.38 ERA in 21 starts. In general, he has a 4.12 career ERA in 102 total big league appearances. The righty dealt with injuries that derailed him between the 2021 and 2024 seasons. But he has been able to stay healthy over the last two seasons and is still young enough to believe there is more in the tank.

When he kicked off his career as a member of the Los Angeles Dodgers, he looked like a potential star of the future. But the injuries slowed him down. Whoever signs him this offseason is going to be betting on his upside, more than his production with the Brewers down the stretch. He still has a blistering fastball and showed flashes with the Cardinals and Brewers in 2026.

Of the teams mentioned by Morosi, the worst-case scenario would be the Cubs. May has the upside to be really good for a club. So, landing with the Brewers' bitter National League Central rival would be bad news. The Padres are a team that should be good in 2027 and could compete with the Brewers for the top spot in the National League. So, May landing there wouldn't be ideal. The White Sox and Astros are in the American League and don't pose much of a threat right now for Milwaukee. So, they would be the best two landing spots, of the ones mentioned by Morosi.

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