Free agent starter with perfect Brewers arsenal could be an interesting target this winter

The Milwaukee Brewers' starting rotation may seem like it's set after Brandon Woodruff accepted the qualifying offer earlier this week, but if there's one thing that the Brew Crew proved in 2025, it's that you can never have enough pitching depth.

If the Brewers are serious about staying on brand with their “pitch lab” identity while still shopping in the second tier of free agency, Dustin May is exactly the kind of arm who should at least be on their whiteboard. Milwaukee has built an entire era of run prevention around fastballs with unusual shapes and sweepers that blur the edges of the strike zone, then trusted their infrastructure to squeeze extra value out of imperfect résumés. May is almost a caricature of that template: a 28-year-old righty with elite raw stuff, a non-traditional pitch mix, and more medical red flags than guaranteed innings. That’s risky. It’s also the exact lane where this front office has done some of its best work.

On top of the baseball questions, May is coming off one of the strangest and scariest roads back to a mound that you’ll ever see. Multiple elbow and arm surgeries already had him fighting uphill when a freak accident nearly cost him his life in July 2024, a piece of lettuce lodged in his throat led to a severe tear in his esophagus and emergency surgery that doctors told him he might not have survived without. That wiped out his 2024 season and forced another long rehab before he finally returned in 2025. 

Brewers’ next rotation lottery ticket might be Dustin May’s risky upside

On paper, the arsenal looks like it was built in a lab in the bowels of American Family Field. May leans on a sweeper/sinker combo that makes up more than two-thirds of his pitch usage, with the sweeper alone sitting around 39 percent.

The sinker and four-seamer give him two distinct fastball shapes, and he’ll flash a cutter and a changeup just enough to keep hitters guessing. In 2025, he struck out just over 21 percent of the batters he faced, and when he did sprinkle in the four-seam, opponents managed a microscopic .165 average against it. That’s exactly the kind of data point the Brewers like to circle: a pitch that already misses barrels, inside a mix that could be reshaped to play even better with their preferred north-south game plan.

There’s also a very clear “fix me” outline for a team that believes in its development machine. May’s sinker, once touted as a wipeout bowling ball, got hit harder in 2025 (.294) than its reputation would suggest. He still used it roughly a third of the time, even as hitters adjusted, which is where Milwaukee’s track record comes into play. This is an organization that’s constantly nudged guys toward better usage — trading sinker-heavy looks for more four-seams at the top of the zone, dialing in sweeper shapes and locations, and finding the right sequencing to unlock an extra tick of whiff rate. With May, the roadmap almost writes itself: lean a little more on the four-seam that hitters can’t square up, fine-tune the sweeper to pair with it, and let the sinker become more of a situational weapon than the backbone of his attack.

Of course, there’s a reason a pitcher with this kind of raw material might be available on a shorter-term deal. May has already gone through one full Tommy John surgery and a later revision procedure, plus that life-altering esophageal tear. 

His 2025 line — a 4.96 ERA with 123 strikeouts across his work for the Los Angeles Dodgers and Boston Red Sox — reads more like a guy still searching for himself than a finished product. That’s a lot of miles, a lot of scars, and zero guarantee that he’ll ever hold up for 30 starts. If the Brewers got involved, it would have to be on exactly those terms: a heavily-incentivized, short-term contract where they’re paying for upside, not pretending he’s a plug-and-play frontline anchor.

And that’s what ultimately makes May a fit for Milwaukee in theory, if not necessarily in practice. He’s not the kind of arm you build a winter around, but he is the kind you sneak into a busy offseason as a calculated gamble: one or two years, a reasonable guarantee, maybe an option year if everything clicks.

For the pitcher, it’s a chance to rebuild value inside one of the best pitching environments in the league. For the Brewers, it’s a shot at turning a medically complicated, stuff-forward free agent into their next quiet success story — the sort of move that looks “interesting” in December and a lot more important if their pitching lab unlocks the version of Dustin May his arsenal still says is in there.