One day after the Brewers won the World Series, Dustin May declined his $20 million mutual option for 2027 and became a free agent, per Jon Heyman of the New York Post on October 29. Milwaukee will pay the $500,000 buyout and walk away clean. May arrived in Wisconsin in August with uneven numbers and leaves with something no other active pitcher can claim: four World Series rings.
The Numbers Behind the Decision
The mutual option was never likely to get picked up. With the Brewers in the regular season, May posted a 5.65 ERA and 1.42 WHIP across 36.2 innings (10 starts) — the worst marks of his year. In the postseason he appeared five times, including two starts, and put up a 5.73 ERA in 11.0 innings. He was never quite the reliable third starter Milwaukee envisioned when they acquired him from the Cardinals on August 3.
But there’s one number the market will pay close attention to: FanGraphs projects a 3.63 FIP for May during his time in Milwaukee, meaning his ERA ran well ahead of how he actually pitched — the hits that landed were more the defense’s problem than his stuff. Combine his Cardinals and Brewers numbers and he finished the regular season at 4.70 ERA, 1.32 WHIP, and 144 strikeouts in 145.2 innings over 31 starts. In the first half with St. Louis he was at 4.38 ERA and 1.28 WHIP — a functional mid-rotation starter, not a disaster.
Four Rings and a Market That Isn’t Sleeping on Him
May enters the offseason as the active pitcher with the most World Series rings in MLB, with four championships. He started his career with the Dodgers, bounced around, and now adds another title with Milwaukee. He’s 29 years old and — perhaps most importantly to whoever signs him — he logged more than 275 combined innings in 2025-2026 after missing the 2023 and 2024 seasons following Tommy John surgery. The arm held up.
Fox Sports values him at approximately $15.4 million in average annual value on the 2026-27 market, citing what they call «rare upside in a thin pitching class.» CBS Sports ranks him No. 25 among the best free agents this offseason, with the Angels, Athletics, and Nationals listed as potential fits. A return to Milwaukee is considered essentially off the table given the team’s profile and budget.
The one complication has nothing to do with May himself: the possibility of a work stoppage in December could freeze the market for pitchers like him before deals get done. If things move fast, he has a real case for landing something close to what Fox Sports projects. If the market stalls, he waits in line with everyone else.
What Milwaukee Takes Away
The Brewers close the offseason with their first World Series title in franchise history, with Jacob Misiorowski and Logan Henderson as the backbone of their rotation going forward, and $500,000 less in the bank from May’s buyout. The August gamble on the Cardinals pitcher didn’t work out on paper, but it wasn’t the deciding factor either — Milwaukee won because of their pitching depth, not in spite of May’s numbers.
For May, the ledger looks different: he finishes 2026 as a champion, coming off his healthiest season since 2022, with a legitimate case for a multi-year deal in a thin pitching market. The ERA sells the wrong story. The FIP and the recent track record tell the real one.
