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Four Teams Emerge As Early Fits for Ex-Brewers' Dustin May Sweepstakes

The Milwaukee Brewers brought Dustin May to town this past summer, but his run with the organization could be one-and-done.

Oct 27, 2026; St. Petersburg, Florida, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch against the Tampa Bay Rays during the first inning in game four of the 2026 World Series at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images | IMAGN IMAGES via Reuters Connect

When the 2026 Major League Baseball trade deadline approached, the Milwaukee Brewers had a major need in the starting rotation. For as good as the Brewers' rotation was in 2026, there were injury concerns throughout the campaign.

Quinn Priester was never able to take the hill for the Brewers in the majors. Brandon Woodruff missed months of action. Kyle Harrison missed some time throughout the campaign. Logan Henderson made just 18 starts in the majors. The only three hurlers who made 20 or more starts for Milwaukee were Jacob Misiorowski, Harrison and Robert Gasser. So, the Brewers looked to add. Dustin May ended up being the guy who came to town.

May didn't put up immaculate numbers in Milwaukee, but he gave the Brewers a consistent option to rely on every fifth day. May made 10 starts down the stretch and then appeared in five playoff games, including two in the World Series. Now, May is a free agent looking for his next home. The Athletic's Tim Britton, Johnny Flores Jr. and Chad Jennings floated four landing spots: the Athletics, Washington Nationals, Houston Astros and the Arizona Diamondbacks.

What To Make Of Early Dustin May Buzz

Oct 15, 2026; Los Angeles, California, USA; Milwaukee Brewers pitcher Dustin May (21) throws during the second inning against the Los Angeles Dodgers in game four of the NLCS for the 2026 MLB Playoffs at Uniqlo Field at Dodger Stadium. Mandatory Credit: Kirby Lee-Imagn Images | IMAGN IMAGES via Reuters Connect

If May isn't going to return to Milwaukee in 2027, which seems likely at this point, the two best options for the Brewers would be if the righty landed with either the Athletics or the Astros. That is because of the fact that both are in the American League.

Of the two, the Astros are more likely to make some noise in the postseason in 2027. The Diamondbacks won 86 games in 2026 and could realistically end up being competition for Milwaukee in 2027.

The Nationals, on the other hand, are still a year or two away from really being a threat. They won 77 games in 2026 and have a very young roster. Still, the Nationals are in the National League, at the very least.

Britton, Flores and Jennings projected that May will cash in with a deal in the range of $36 million over two years this winter. From a pure talent perspective, it would be nice to have May with the organization for a full year in 2027.

He has plenty of talent and is just 29 years old. The Brewers are a team that could get the most out of him, but that projected price tag is far too high to imagine Milwaukee being involved. So, at this point, it seems like May's run in Milwaukee is likely over.

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