As baseball’s Winter Meetings approach, all eyes in Milwaukee are on Matt Arnold and the Brewers' front office. December is here, and with the 2025 Winter Meetings just a week away, the question is simple: will the Brewers make a splash?
If history is any guide, Arnold’s track record suggests we shouldn’t expect fireworks for the sake of headlines-but when he moves, it’s usually with purpose.
2022: A Mixed Bag, but a Clear Win
Arnold’s first Winter Meetings at the helm came in 2022, and the results were... complicated.
The Kolten Wong trade, which sent the veteran second baseman to Seattle in exchange for Jesse Winker and Abraham Toro, looked like a fair deal at the time. Wong was coming off a solid season, Winker had an All-Star appearance on his resume, and Toro had flashed some upside.
But things unraveled quickly. Wong never got going in Seattle and was designated for assignment by August.
Winker’s stint in Milwaukee was forgettable at best-he struggled at the plate and reportedly wore out his welcome in the clubhouse. Toro, meanwhile, showed promise in limited action, but was flipped that offseason for pitcher Chad Patrick-a deal that, in hindsight, has tilted in the Brewers’ favor.
But the real gem came just after those Winter Meetings, when Arnold pulled off what remains his signature move: the trade that brought William Contreras, Joel Payamps, and Justin Yeager to Milwaukee in exchange for Esteury Ruiz.
Now, Ruiz did make noise in 2023 by swiping 67 bases and setting a new AL rookie record, but he never developed into a complete offensive threat. Injuries and inconsistency derailed his 2024 and 2025 seasons, and by year’s end, he’d been designated for assignment again after a brief stint with the Dodgers.
Contreras, on the other hand, has blossomed into one of the best catchers in baseball. A Silver Slugger in 2023, an All-Star in 2024, and a consistent 4+ bWAR player-he’s become a franchise cornerstone.
Payamps gave the Brewers two solid seasons out of the bullpen before being DFA’d in 2025, and Yeager never cracked the big-league roster, finishing his Brewers tenure in Triple-A before hitting free agency. Still, this was a clear win for Milwaukee, and it all started with conversations during those Winter Meetings.
2023: All Quiet on the Trade Front
The 2023 Winter Meetings were quieter across the board, and Milwaukee was no exception. There were rumblings about a Corbin Burnes trade, but nothing materialized until February.
The entire league seemed to be in a holding pattern, thanks in large part to the Shohei Ohtani sweepstakes. With teams hesitant to commit big money until Ohtani made his decision, the Brewers sat tight-and they weren’t alone.
2024: Quiet Moves, Big Impact
Fast forward to last year. Once again, the Brewers didn’t make a headline-grabbing move during the Winter Meetings, but shortly after, they pulled the trigger on another impactful trade: Devin Williams to the Yankees for Caleb Durbin and Nestor Cortes.
Williams, a two-time NL Reliever of the Year, had been a dominant force in Milwaukee’s bullpen. But after a shaky postseason outing and with free agency looming, the Brewers decided to move on. The return didn’t wow at first glance-Durbin was seen as a versatile but unproven infielder, and Cortes was coming off an injury-plagued season.
But once again, Arnold’s patience paid off. Durbin turned into a key contributor during Milwaukee’s record-setting 2025 campaign, providing defensive flexibility and timely hitting.
Cortes made only a few appearances before being flipped to San Diego for outfielder Brandon Lockridge. Meanwhile, Williams struggled in New York, losing his closer role early and finishing the year with a 4.79 ERA.
Now a free agent, there’s even chatter he might return to Milwaukee to reset his value.
Also worth noting from 2024: the Brewers selected Connor Thomas in the Rule 5 Draft and signed Grant Wolfram to a major league deal. Neither move made an impact.
Thomas gave up 12 runs in just over five innings before hitting the IL with elbow arthritis. Wolfram was traded to the Orioles the day after being DFA’d, without ever throwing a pitch for Milwaukee.
These were low-risk gambles that didn’t pan out-but they didn’t cost the team much, either.
What Can We Expect in 2025?
If there’s a pattern to Arnold’s Winter Meetings approach, it’s this: he doesn’t move just to make noise. The deals he’s made-especially the Contreras and Williams trades-were calculated, forward-looking, and ultimately beneficial for the Brewers. Even the smaller moves that didn’t pan out (Thomas, Wolfram) were low-risk swings that didn’t hurt the club long term.
So, should we expect Milwaukee to be active next week? Maybe. But only if the right opportunity presents itself.
Arnold has shown he’s willing to wait for the right deal, even if it means doing business after the meetings wrap up. When he does strike, it’s usually because he sees real value-not just a name or a headline.
If a big trade goes down, history says it won’t be reckless. It’ll be smart, strategic, and likely to pay off down the road.
So stay tuned. The Winter Meetings are coming, and while Milwaukee might not dominate the rumor mill, don’t be surprised if they walk away with another under-the-radar win.