Brewers' Dustin May makes unsurprising free agency decision after securing MLB-leading fourth ring

Trade deadline acquisition Dustin May didn't have as big of an impact on the Milwaukee Brewers' 2026 World Series run as the front office was hoping for when they added the veteran right-hander from the St. Louis Cardinals on August 3. Expected to be the Milwaukee's clear-cut No. 3 postseason starter when he joined the MLB-best Brewers for the final months of the 2026 season, May ended up filling a more versatile, lower-leverage role in the World Series. He appeared as a middle reliever in Game 2 and covered three innings at the beginning of Game 4 of the Brewers' World Series defeat of the Tampa Bay Rays.

While May, who finished with a 5.73 ERA in 11 innings pitched during this year's postseason, didn't quite live up to the high expectations that his track record and potential-laden arsenal built, the right-hander will always have a spot in Brewers' history as one of the 26 players who were rostered on the franchise's first World Series-winning roster.

May also currently holds a place among MLB leaders due to securing his fourth ring on Wednesday night. While May has only pitched in two World Series -- 2020 and 2026 -- he now has four World Series rings due to the part that he played in the Los Angeles Dodgers 2024 and 2025 campaigns. Though May didn't pitch in either of the Dodgers' back-to-back World Series titles in each of the last two seasons, as a member of the roster at one point in the season, he still earned a ring. As a result, May has an impressive four World Series rings before his 30th birthday, which is tied with Mookie Betts for the most among active players in MLB.

While May will forever be remembered as a part of the Brewers' 2026 World Series team, it was never likely that the right-handed starter would remain in Milwaukee long term. May was seemingly always destined for free agency at the completion of the 2026 season, and on Thursday afternoon he made it official by declining the mutual option that was included in his one-year deal with the Cardinals, and inherited by the Brewers via trade. As such, just one day after the Brewers won the World Series, May is officially a free agent -- and one who is unlikely to re-sign with Milwaukee this offseason.

Dustin May declines mutual option, hits free agency ahead of modified offseason

Mutual options, which involve the player and club concurring on a previously agreed-upon salary figure, are hardly ever picked up in MLB. Rather, they serve as an opportunity for teams to defer salaries, as they are almost always accompanied by a buyout figure that is exercised when the mutual option is declined. For example, May's $20 million mutual option for the 2027 season included a modest $500,000 buyout, which the Brewers are on the hook for after inheriting the contract at the trade deadline.

It's unsurprising that May declined his end of the deal, seeing as he's likely to bring in more than $20 million in guaranteed money this offseason, presumably over the course of a longer-term deal. While May's time with the Brewers and overall body of work during the 2026 season may have been underwhelming, he certainly showed flashes of brilliance that, at just 29 years old, are likely to earn him a relatively lucrative multi-year deal in what is a starved starting pitching market.

The Brewers, though May does fit their pitching philosophy well, are unlikely to be the ones giving the four-ring-bearing right-hander a long-term contract this offseason. With troves of controllable starting pitching options, and without a track record of signing free-agent starting pitchers, seeing the Brewers and May link up for a multi-year deal before the work stoppage in December is all but impossible.

From an individual standpoint, it didn't work out great for May in Milwaukee, but such a takeaway feels unimportant as the Brewers flaunt the Commissioner's Trophy, especially when the midseason trade acquisition did pitch in the World Series. However, regardless of his impact on the Brewers' first title-winning season, May's time in Milwaukee was always going to be short-lived, and the declining of his mutual option on Thursday night was simply the first step of that reality.

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