Brewers GM makes history after Milwaukee’s record-breaking 2025 season

Matt Arnold didn’t just pick up another trophy on Nov. 13; he made MLB history. The Milwaukee Brewers’ general manager became the first person ever to win Executive of the Year twice, and he did it in back-to-back seasons (2024 and 2025). That alone says a lot. Put it next to what Milwaukee just did on the field, with the best record in baseball, 97 wins in 2025, and another NL Central title, and it looks less like a fluke and more like a front office that knows exactly what it’s doing.

The Brewers aren’t some heavyweight spender that can just throw money at its problems. They’re a small-market club that has to get their evaluations right, live with some uncomfortable trades, and still figure out how to stay in the race every single year. Arnold’s managed to walk that line without blowing it up for a full teardown or shoving all the chips in for one desperate run. He’s kept Milwaukee in the fight while turning over big chunks of the roster, and now the hardware he’s winning lines up with what the standings have been saying.

Matt Arnold’s back-to-back Executive of the Year awards prove Brewers’ model is built to last

You see it most clearly in the star trades that could’ve gone sideways fast. Instead of letting Corbin Burnes walk for nothing, Arnold moved him before the 2024 season and turned him into Joey Ortiz and DL Hall, who jumped in and helped right away. He did basically the same thing with Devin Williams before 2025, dealing an elite closer and turning that into more depth with Caleb Durbin and Nestor Cortes. Those moves didn’t exactly win the press conference, but they kept the Brewers younger, deeper, and cheaper without waving the white flag on the present.

He backed that up by finding the right kind of help outside the organization with Rhys Hoskins and José Quintana. Around them, quieter additions like Grant Anderson and Jared Koenig turned into legitimate pieces. That’s the kind of stuff that doesn’t always lead to a headline but shows up every day from April through October.

Arnold’s biggest swing might have been on a player who hadn’t even debuted yet. Signing Jackson Chourio to an eight-year deal with two club options before he played a Major League game was a record-setting gamble for a pre-debut player. It’s already aging well. Chourio quickly became the youngest player ever to post back-to-back 20-homer, 20-steal seasons, giving the Brewers a cost-controlled star to build around and a clear face of the next era in Milwaukee.

Even the dugout reflects Arnold’s approach. When Craig Counsell left, it could’ve been a natural breaking point. Instead, Arnold stayed in-house and promoted longtime bench coach Pat Murphy to manager. The continuity mattered. Murphy knew the clubhouse and the organization, and he quickly managed himself into a two-time NL Manager of the Year. The Brewers changed leaders without losing their identity.

Add all of this up, and Arnold’s back-to-back Executive of the Year awards make sense. He traded stars without punting seasons, locked up a franchise cornerstone before the rest of the league fully realized what he was about to become, and kept layering in smart depth around the edges. As long as Matt Arnold is calling the shots, the Brewers don’t look like a team simply crashing a party. They look like one that plans on sticking around.