Brewers Already Face A Painful Offseason Question After October

The Milwaukee Brewers face significant changes as they enter the offseason, losing key players like Brandon Woodruff to free agency following their World Series triumph.

The Brewers’ offseason ledger opened Thursday with four familiar names hitting free agency, and Brandon Woodruff sits at the top of that list.

Milwaukee also saw Jake Bauers and JoJo Romero officially become free agents, while Dustin May declined his mutual option and joined them on the market. That group comes right after the 2026 World Series wrapped earlier in the week, which triggered the offseason shuffle across Major League Baseball.

Bauers is the loudest success story of the bunch. He came into 2026 with a resume that looked modest enough: over 100 games in a season only three times, never more than 117 in one year, never more than 12 home runs, and never a batting average above .235.

Then he blew past all of that. He played in 144 games, hit .266/.389/.484 with 26 home runs and 86 RBIs, and was named the National League Championship League Most Valuable Player.

That kind of season put him in line for a strong payday, whether that ends up being with Milwaukee or somewhere else.

Woodruff’s situation feels different. He’s technically on the open market now, but if he keeps pitching in 2027, it would be a major surprise to see him anywhere other than Milwaukee.

He spent months working his way back so he could take the mound for the Brewers in the World Series, and he has spent his entire career with the club. Given his recent injury history, the price tag is expected to be reasonable, and if he does play again next year, the Brewers look like the obvious home.

Romero also has a case to return if the money lines up. Milwaukee picked him up from the St.

Louis Cardinals, then activated him off the Injured List, and he delivered. In the regular season, he posted a 3.38 ERA in 11 appearances down the stretch.

He was even sharper in October, finishing with a 1.13 ERA in seven postseason outings. That kind of finish makes him a logical target for a reunion.

May was the other summer trade pickup to hit free agency. His Milwaukee stat line wasn’t flashy, but he filled the role the Brewers needed. He gave the club rotation depth and contributed in the playoffs, and now he’s positioned for a solid contract that could easily come from another team.

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