The Brewers' best move from each of the last three offseasons (2022-2024)

When former Milwaukee Brewers' President of Baseball Operations David Stearns stepped down from his role following the 2022 season, Brewers fans didn't know what to think. During Stearns' tenure, the Crew qualified for four consecutive postseasons from 2018-2021, something that had never been accomplished in franchise history. On top of that, Stearns found a new face of the franchise in Christian Yelich, who carried his team to a National League Championship Series appearance during his 2018 MVP campaign. In almost every regard, the Brewers were an incredibly successful organization under Stearns' guidance. Therefore, when Matt Arnold assumed the role as the head of the Brewers front office, starting during the 2022-23 offseason, Brewers fans were hoping he possessed the same "Midas Touch" that his predecessor seemed to have.

Almost immediately, Arnold proved his value, executing one of the best trades in franchise history. He followed it up by handing a record-breaking contract to the new face of Milwaukee's franchise the following offseason, before executing a series of blockbuster deals that turned the Brewers' departing stars into controllable talent. The result of these three highly successful offseasons with Arnold at the helm has not only been three-consecutive NL Central titles, but also a team whose competitive window doesn't appear to be closing anytime soon. Let's take a deeper dive into the best moves from each of Arnold's three offseasons as the head of the Brewers' front office.

2022-23: Brewers acquire William Contreras in three-team blockbuster

When the Brewers acquired William Contreras, Joel Payamps, and Justin Yeager in a three-team blockbuster that sent catcher Sean Murphy to the Atlanta Braves, fans couldn't believe that all Arnold had surrendered to bring in an All-Star catcher with five years of team control was outfield prospect Esteury Ruiz. Nothing against Ruiz, he was an intriguing prospect at the time who was a key piece in the Josh Hader trade just months earlier, but the Brewers made out like bandits after sneaking their way into the three-team deal.

Since the trade, Contreras has earned two Silver Slugger Awards, made the 2023 NL All-Star team, received NL MVP votes in both 2023 and 2024, and has led his team to an NL Central title in each of his three years wearing a Brewers uniform. Contreras holds a 122 OPS+ since joining the Brew Crew, and has averaged 19 homers per season. After a 2.6 WAR season with Atlanta in 2022, Contreras has posted seasons of 3.7, 4.9, and 3.9 WAR during his first three years in Milwaukee, highlighting that not only is he a strong offensive backstop, but his defense has improved significantly since joining the Brewers.

Not only was this clearly Arnold's best move of the 2022-23 offseason, it's possibly the best move he's ever made as the head of the Brewers' front office and one of the best trades in franchise history. Contreras has become a cornerstone of the Brewers' success in the last three years, not only leading with his play on the field, but also in the clubhouse. Add to that the role that he's played in continuing the success of the Brewers' pitching staff, and this trade looks even more lopsided in Milwaukee's favor.

2023-24: Jackson Chourio inks eight-year contract before making his MLB debut

While there appeared to be very little risk involved in the Contreras trade at the time of its execution, Arnold's best move of the 2023-24 offseason was one of the riskier moves the Brewers have conducted in recent history. Prior to making his MLB debut, Jackson Chourio signed an eight-year contract that guaranteed him $82 million -- the most money ever given to a player who had yet to appear in MLB.

There's absolutely risk involved in giving a player a contract of that size before he even faces big-league competition, but Chourio, who was MLB Pipeline's No. 2-ranked prospect in all of baseball at the time, looked as close to a sure-bet as there is in baseball. He not only had an impressive amount of success at a very young age in the upper levels of the minor leagues, but the tools that he displayed were undeniable. From lightning-quick hands at the plate, opposite-field pop, speed on the basepaths, and a decently strong glove in the outfield, the Brewers were smart to sign Chourio to an extension before he proved just how good of a big-leaguer he could be.

The decision to sign an extension with Chourio before he debuted rather than a few games into his MLB career likely saved the Brewers somewhere in the range of $40-50 million. Just last year, outfield prospect Roman Anthony, who carried similar hype to Chourio coming out of the minor leagues, signed an eight-year, $130 million extension in part because the Red Sox waited until he had played 50 MLB games to agree to the deal. Arnold and the Brewers' front office's foresight not only saved them money, but it also gives them a new franchise player to build around for the foreseeable future.

2024-25: Brewers acquire Caleb Durbin in trade that sends Devin Williams to New York Yankees

The 2024-25 offseason was a quiet one for Arnold and company, in large part due to the work they'd put in during previous offseasons to build a roster that was going to be competitive for years to come. Outside of losing Willy Adames to free agency, the Brewers' major move last offseason was trading their All-Star closer Devin Williams to the New York Yankees in exchange for infield prospect Caleb Durbin and veteran starter Nestor Cortes.

Coming off an impressive performance in the Arizona Fall League, Brewers fans were energized by the addition of Durbin, but most would be lying if they anticipated the rookie campaign that he ended up putting together in 2025. After a 2.8 WAR season in which Durbin demonstrated his value in the field, at the plate, and on the basepaths, the 25-year-old infielder was named a finalist for the National League's Rookie of the Year Award. Though he ended up finishing in third place, his place among the league's top rookies has Brewers fans excited about Durbin's future.

Making the trade even better was the inconsistent season that Williams turned in for the Yankees in 2025. With a 4.79 ERA, four blown saves in 22 opportunities, and an end to his role as the closer very early in the season, Williams produced his worst season of his career in 2025. Paired with the breakout year Durbin turned in, the Brewers are the clear winners of their deal with the Yankees last winter, which was easily their best move of the offseason.