The Milwaukee Brewers made franchise history in 2025 with 97 regular-season wins and their first playoff series win since 2018, yet their season ended in disappointment with a sweep at the hands of the Dodgers in the NLCS. As the front office and coaching staff turn to the offseason, there are crucial questions that will determine whether Milwaukee can take the next step toward its first World Series title.
The Biggest Questions the Brewers Must Answer This Offseason
What Will the Starting Rotation Look Like in 2026?
The rotation was a key strength but also an area of uncertainty. Freddy Peralta remains a cornerstone, but veteran arms Brandon Woodruff and Jose Quintana may not return if their options are declined. Corbin Burnes faces his last arbitration-eligible year, with the team weighing trade possibilities to avoid losing him for nothing in free agency.
The Brewers will also rely on young arms like Jacob Misiorowski and Quinn Priester, but the staff needs veteran stability to guide them. Whether through re-signings, trades, or free agency, finding that experienced presence will be vital.
How Will the Brewers Address the Shortstop and Outfield Positions?
Offensively, shortstop was one of the weakest spots last season, with Joey Ortiz providing solid defense but scarce run production. Milwaukee could pivot by moving Brice Turang to shortstop. This would free up second base and inject energy both in fielding and hitting. If not, the front office might look externally for upgrades.
In centerfield, injuries forced a patchwork of options, and while players like Sal Frelick showed promise. The Brewers may need an outfielder with more power to complement the lineup’s balanced approach. These positional questions tie directly into the team’s offensive philosophy of balancing power with consistency in key spots.
What Contract and Roster Moves Will Shape the Brewers’ Future?
The Brewers face significant arbitration and free agency decisions, particularly around pitchers Woodruff, Burnes, and others who could reach free agency or be non-tendered. Meanwhile, the team must decide how much to invest in its homegrown talent. They need to support and develop rookies ready to make their MLB impact.
The approach will determine whether Milwaukee pursues a quick retool to remain a contender or takes a deeper restructuring approach. General manager Matt Arnold has signaled the desire to compete now. This avoids a rebuild, but understanding that smart, perhaps quiet moves are necessary to overcome postseason hurdles.
Can the Brewers Evolve Their Offensive Approach?
After years of being criticized for over-reliance on the long ball, Milwaukee’s offense grew more versatile in 2025. The Crew had particularly strong run production in the second half. However, more power will be needed to challenge powerhouse lineups in the playoffs. Christian Yelich’s power hitting has waned, so external additions or internal development for added power are priorities.
The Brewers’ 2025-26 offseason will be about balancing continuity with calculated upgrades. They will look to blend experienced veterans with emerging stars and need to address apparent positional gaps. This is all while aiming to build on a historic season and finally break through to the World Series.
The decisions made now will reverberate through the coming years. They will define Milwaukee’s window of contention and its pursuit of championship glory that has eluded the franchise for over a century. Fans will be watching eagerly, and likely a bit anxiously.
Main Photo Credits: Kirby Lee-Imagn Images
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