When David Stearns stepped down as the Milwaukee Brewers’ President of Baseball Operations after the 2022 season, it marked the end of an era. Under Stearns, the Brewers reached the postseason four straight years from 2018 to 2021-a feat never before achieved in franchise history.
He brought Christian Yelich to Milwaukee, who promptly won the 2018 NL MVP and powered the team to the brink of a World Series. Stearns helped build a winner, plain and simple.
So when Matt Arnold stepped into the big chair during the 2022-23 offseason, expectations were sky-high. Brewers fans weren’t just hoping for continuity-they were hoping Arnold could keep the momentum going and maybe even push the franchise further.
Three offseasons later, it’s safe to say he’s done exactly that. With three straight NL Central titles and a roster built for sustained success, Arnold has made his mark.
Let’s break down the defining move from each of his first three offseasons leading the Brewers’ front office.
2022-23: William Contreras Trade Becomes a Franchise Cornerstone
Arnold’s first major move in charge was a masterstroke. In a three-team deal that sent Sean Murphy to Atlanta, the Brewers landed William Contreras, Joel Payamps, and Justin Yeager.
The cost? Outfield prospect Esteury Ruiz.
At the time, Ruiz was a promising young player who had been part of the Josh Hader trade just months earlier. But getting an All-Star catcher with five years of team control in exchange for a prospect-no matter how intriguing-is the kind of trade that front offices dream about.
Since arriving in Milwaukee, Contreras has been everything the Brewers could have hoped for and more. He’s picked up two Silver Slugger Awards, made the 2023 NL All-Star team, and received MVP votes in both 2023 and 2024.
He’s also helped lead the Brewers to division titles in all three of his seasons with the club. Offensively, he’s posted a 122 OPS+ and averaged 19 home runs per year-numbers that put him among the league’s elite at the catcher position.
But perhaps most impressive is how much his defense has improved. After a 2.6 WAR season in Atlanta in 2022, Contreras has posted WAR totals of 3.7, 4.9, and 3.9 in his first three seasons in Milwaukee.
That jump reflects not just his offensive consistency, but also his growth behind the plate. His work with the pitching staff has been a key part of the Brewers’ continued success, and his presence in the clubhouse has made him a true leader.
This wasn’t just Arnold’s best move of the 2022-23 offseason-it might be the best trade in Brewers history. Contreras has become a foundational piece, and the Brewers are reaping the rewards.
2023-24: Brewers Bet Big on Jackson Chourio Before First Pitch
The following offseason, Arnold took a much different approach-one that carried a lot more risk. Before Jackson Chourio had played a single inning in the big leagues, the Brewers handed him an eight-year, $82 million contract. It was the richest deal ever given to a player who hadn’t yet made his MLB debut.
That kind of gamble doesn’t come lightly. But Chourio wasn’t just any prospect.
At the time, he was ranked as the No. 2 overall prospect in baseball by MLB Pipeline. He had already shown he could handle upper-level minor league pitching at a young age, and his tools were off the charts: elite bat speed, power to all fields, speed on the bases, and solid defense in the outfield.
The Brewers saw enough to lock him up early-and that decision could end up saving them tens of millions down the line. Just look at Roman Anthony, a similarly hyped outfield prospect who signed an eight-year, $130 million extension with the Red Sox after just 50 MLB games. By getting ahead of the curve, Milwaukee secured a potential franchise player at a significant discount.
It was a bold move, no doubt. But it also showed that Arnold and the Brewers are thinking long-term.
They weren’t just betting on Chourio’s talent-they were betting on their player development, their scouting, and their belief in the young star. So far, it looks like a bet that’s going to pay off.
2024-25: Caleb Durbin Emerges in Deal That Sends Devin Williams to Yankees
Heading into the 2024-25 offseason, the Brewers didn’t have many holes to fill. Thanks to Arnold’s previous moves, the roster was already built to compete. But they still made one significant trade, sending All-Star closer Devin Williams to the Yankees in exchange for infield prospect Caleb Durbin and veteran starter Nestor Cortes.
At the time, the move raised eyebrows. Williams had been a dominant force in the Brewers’ bullpen, and while Durbin had flashed potential-especially during a strong showing in the Arizona Fall League-he wasn’t exactly a household name. But by the end of the 2025 season, it was clear that Milwaukee had come out on top.
Durbin’s rookie campaign was a revelation. He posted a 2.8 WAR season, showcasing his versatility in the field, consistent production at the plate, and speed on the bases. He finished as a finalist for the NL Rookie of the Year Award, ultimately placing third, but his emergence gave the Brewers yet another young building block.
Meanwhile, Williams struggled in New York. He posted a 4.79 ERA, blew four saves in just 22 chances, and lost his closer role early in the season. It was the worst year of his career, and it made the trade look even better from Milwaukee’s perspective.
Durbin’s breakout, combined with Williams’ downturn, made this deal a clear win for the Brewers-and another feather in Arnold’s cap.
Bottom Line: In just three offseasons, Matt Arnold has put together a résumé that rivals any executive in the league. He’s pulled off a franchise-altering trade, locked up a generational talent before his debut, and turned a high-profile closer into a breakout infield prospect.
The Brewers aren’t just winning-they’re building something sustainable. And with Arnold steering the ship, Milwaukee’s competitive window looks wide open.