westhawaiitoday
Amid the euphoria of the Milwaukee Brewers' World Series celebration, with 50 Cent's anthem about underdogs blaring and champagne mist filling the air, veteran Brandon Woodruff took a moment to soak it all in. The longest-tenured Brewer, at 33, looked around and saw his youngest teammates—Jackson Chourio, Cooper Pratt, Jacob Misiorowski, and Logan Henderson—all champions before their 25th birthdays. "Dang, I'm so glad those guys are getting to experience this because it's so good for them," Woodruff said. "It's crazy. It's like, all they know is winning."
That winning culture didn't happen overnight. Milwaukee has reached the postseason in every year but one since 2018, and they posted the best record in baseball in both 2025 and 2026. Now, as first-time World Series champions, the Brewers' roster outlook and track record suggest that a small-market dynasty is within reach. "Our window is open for a while," center fielder Garrett Mitchell said.
The Brewers' core of young, homegrown position players—athletes who hit, as president of baseball operations Matt Arnold describes them—are all under club control for at least a couple more years, if not considerably longer. Chourio, one of the game's most electrifying young talents at 22 and already with three straight 20-20 seasons to begin his career, is under contract through 2033. His salary won't exceed $9.25 million until he makes $15.25 million in 2029. After signing Chourio to an extension before his debut in 2024, the Brewers followed the same blueprint in locking up rookies Cooper Pratt and Luis Lara through 2035. Optimistically, those three could enter their primes together in a few years while costing approximately $25 million combined—roughly what Christian Yelich is set to make next season alone ($27 million).
The biggest future decision for the Brewers, who almost always seek a return before a player hits free agency, may not come until they hit a crossroads with second baseman Brice Turang, another budding star. MLB Trade Rumors projects Turang, who led the Brewers position players with a 5.9 fWAR, to make $9.5 million in 2027. After that, he holds two more arbitration years, though he is only getting more expensive. "The future, man, is going to be great," Turang said. "We have a lot of really talented young players who learned from some vets who are leaders."
Every year, however, the Brewers must overcome the constraints of their market and the spending limit owner Mark Attanasio imposes. Their most pressing issue, for example, is what to do with World Series MVP William Contreras, their heartbeat and catcher. The Brewers hold a $14.5 million club option on Contreras for next season before he is slated for free agency. They face a similar dilemma with closer Trevor Megill, who is entering his final year of arbitration in 2027. In similar cases from previous years—Devin Williams, Corbin Burnes, Josh Hader, Freddy Peralta—the Brewers made trades that bolstered their farm system. It's part of how they've kept chugging along without signing high-priced free agents. It's also a part of why they're so well-positioned to continue chugging along.
Reinforcements are seemingly always on the way. The Brewers have both the consensus No. 1 prospect in baseball, Jess Made, and the consensus No. 1 farm system in baseball. They rank toward the bottom third of the league in player payroll, yet they are rich in prospect capital. That's a product of spending resources to improve processes behind player acquisitions, the draft and the international market. Continuity runs deep within the Brewers front office and major-league coaching staff. Plenty of it is poised to continue. In spring training, manager Pat Murphy signed a three-year deal.
Once the Brewers acquire players, they are good at developing them or making them better. For so many years, Milwaukee was on the cutting edge of pitching development, but its hitting group lagged. That is no longer the case. Still, their ability to help unheralded pitchers reach new levels remains, and it's a trait that needs to come in handy again.
Many people within the Brewers consider their 2021 team their best before the emergence of their 2026 group. The difference between the rosters is that the World Series champions boast a much better lineup. Five years ago, the Big Three of Woodruff, Burnes and Peralta led the Brewers. This Brewers iteration doesn't have such a dominant trio. It also doesn't need to. Misiorowski, baseball's hardest thrower and its most valuable pitcher (6.6 fWAR), is just 24. He is the favorite to win the National League Cy Young Award—two years from being eligible for arbitration. Misiorowski, in his second year in the majors, belongs in a class of his own. But the Brewers could do a lot worse than Logan Henderson as Robin to their Batman. As a rookie, Henderson burst onto the scene as a dependable No. 2. Like Misiorowski, he is five years away from free agency.
Unlike five years ago, the Brewers do not have a clear-cut No. 3 in their rotation. There are, however, a bunch of candidates who Milwaukee officials believe can at least make up production in the aggregate: Kyle Harrison, Shane Drohan and Robert Gasser are among them. And, yes, none of them are anywhere near free agency. In the farm system, club officials are bullish on prospects such as Tyson Hardin, Bishop Letson and Josh Knoth, who all reside in the upper levels of the minors. "We try to stay in the now a lot, but seeing how young a lot of our arms are, it's pretty cool to think about how we could be doing this for a long time, be able to sustain it and keep going with each other," Henderson said.
The Brewers did not have Misiorowski or Henderson to carry them in the postseason. At times, it looked as if the pair was operating on fumes. The Brewers pushed their workloads. Pitching coach Chris Hook said they might be better in the long run because of the experience. Instead of the rotation leading them, the Brewers bullpen did much of the heavy lifting in the postseason with dominant performances from Abner Uribe and Aaron Ashby. Milwaukee plucked Uribe from the Dominican Republic for an $85,000 signing bonus in 2018 and extended Ashby in 2022 for five years (plus two club options) after taking him in the fourth round of the 2018 amateur draft.
The Brewers are like the MLB's version of the NBA's Oklahoma City Thunder, which followed up a title run with a trip this year to the conference finals. Oklahoma City is another small-market success story in sports, with a mix of highly productive players and others who simply perform roles exceptionally well. A salary cap, however, has altered the complexion of its roster. Baseball's economic landscape is unknown with the current labor agreement set to expire during the offseason, but Milwaukee's front office has demonstrated deft nimbleness regardless of rule changes or other challenges. The context is different now. The Brewers, at last, are World Series champions. But that doesn't mean much might change.
Originally reported by westhawaiitoday.