Brewers Biggest Question Looming Over Milwaukee Before NLDS

The Milwaukee Brewers have one big question, above all else, heading into the NLDS.

Sep 22, 2026; Philadelphia, Pennsylvania, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch during the first inning against the Philadelphia Phillies at Citizens Bank Park. Mandatory Credit: Eric Hartline-Imagn Images | IMAGN IMAGES via Reuters Connect

The Milwaukee Brewers have three days to go before they will begin their quest in the 2026 playoffs. Milwaukee will face either the San Diego Padres or the Chicago Cubs in the National League Division Series with the series set to kick off in Milwaukee.

If the Padres win on Wednesday night, they will punch their ticket to face off against Milwaukee. Beyond Game 1 on the National League Division Series, Milwaukee is six days away from answering the biggest question hanging over the team heading into the playoffs: Who starts Game 3?

Jacob Misiorowski is going to get the ball in Game 1 and Logan Henderson is currently scheduled to take the hill in Game 2. As of writing, the Brewers haven't announced who will be their Game 3 starter. If Kyle Harrison didn't struggle down the stretch, this wouldn't even be a topic. He either would've started Game 2, with Henderson pushed to Game 3. Or, Henderson would've taken Game 2 with Harrison in Game 3. The same could be said if Brandon Woodruff didn't get hurt. He'd certainly be penciled in for one of those early games with Game 3 being the latest. But here we are.

There are two options who stand above all else: Robert Gasser and Dustin May.

Who Will Start A Game 3 For Milwaukee?

Sep 25, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Robert Gasser (54) prepares to deliver a pitch against the St. Louis Cardinals in the fourth inning at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images | IMAGN IMAGES via Reuters Connect

When the Brewers acquired May from the St. Louis Cardinals and Harrison started struggling, the big righty seemed like the most obvious option to start a Game 3. And that may very well happen, but he also wasn't perfect down the stretch. May actually hasn't pitched more than three innings in a game since Sep. 11. May has made 10 appearances for Milwaukee and has pitched fewer than four innings in six of them. The tenure began well, but has shifted.

Gasser, on the other hand, ended the regular season on a high note and logged a 1.67 ERA in his final six appearances of the season across 32 1/3 innings of work. The Brewers went 5-1 in the six games Gasser appeared in down the stretch. He hasn't allowed more than one run in a game since Sep. 1.

On paper, it shouldn't even be a debate. Gasser has been better down the stretch and should get the ball in a Game 3. May has plenty of playoff experience, which works in his favor. But Gasser has been better.