The Milwaukee Brewers pushed all of the right buttons throughout the 2026 Major League Baseball season, to say the least.
Milwaukee racked up a franchise-best 103 wins in the regular season and followed up by going on to win the first World Series in franchise history. The season couldn’t have gone better for Milwaukee. The 2027 roster may not look exactly the same, but the 2026 team will always be remembered. Now, the offseason is here, though. We will start to see movement soon and four members of the organization already have gone to free agency in Brandon Woodruff, Jake Bauers, JoJo Romero and Dustin May. It would be nice to have the entire roster back, but that’s not realistic. We’re at a point in the offseason in which speculation and rumors begin.
One example of this is CBS Sports listing May as the 25th-best free agent of the offseason, but not listing Milwaukee as a potential landing spot. Instead, the Los Angeles Angels, Athletics and Washington Nationals were floated.
“No. 25. RHP Dustin May,” CBS Sports’ Mike Axisa wrote. “Potential landing spots: Angels, Athletics, Nationals. … It is not the best sign, though, that the Brewers, who know pitching as well as any team, couldn’t fully unlock May after making him their big deadline rotation addition. Still, the combination of age and high-octane stuff makes him a nice upside play on a short-term contract, particularly for a rebuilding team that is willing to run him out there every fifth day regardless of results.”
In Milwaukee, May made 10 starts down the stretch in the regular season and had a 5.65 ERA and a 38-to-15 strikeout-to-walk ratio in 36 2/3 innings pitched. He pitched in five playoff games, including two starts, and had a 5.73 ERA in 11 innings pitched.
May didn’t have the production on the mound that he likely wanted to have in Milwaukee, but he gave the Brewers a depth arm that they needed at the time. At the end of the day, the Brewers got what they needed, but this idea of May potentially not coming back also makes a lot of sense.
When it comes to Milwaukee’s internal free agents, it should be putting a focus on Bauers, Woodruff and maybe even Romero. It wouldn’t be a shock to see May get paid more elsewhere. May spent a few months in Milwaukee and came away with a ring. At the end of the day, that’s a success, even if the partnership is short-lived.
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