A Brief History of Matt Arnold at the Winter Meetings

Today is December 1, which means that the 2025 Winter Meetings are just a week away. Should we expect the Brewers to be active?

Let’s take a look at what Matt Arnold has done at the Winter Meetings since being named general manager/president of baseball operations.

Kolten Wong traded to the Mariners for Jesse Winker & Abraham Toro

While this trade initially looked promising for both teams, none of the players involved did much for the teams that acquired them. Wong didn’t even make it a full season with Seattle, hitting just .165 before being designated for assignment on August 1. Winker was terrible (.567 OPS) as a Brewer and burned every bridge possible on his way out of town. Toro played well in very limited time with Milwaukee, but was traded straight-up for Chad Patrick that offseason — a deal that the Brewers appear to have won so far.

Esteury Ruiz traded to the Athletics for William Contreras, Joel Payamps, & Justin Yeager

This was technically completely the week after the Winter Meetings, but I’m throwing it in because a) trade talks reportedly started at the Winter Meetings and b) it’s probably still Arnold’s best trade. While Ruiz stole 67 bases in 2023, breaking the AL rookie stolen base record, he was never able to post an OPS over .654 with the A’s. He missed most of the 2024 season with a wrist injury, started 2025 in the minors, and was eventually DFA’ed. Ruiz appeared in 19 games with the Dodgers last season, going 4-for-21 with a home run.

William Contreras needs no introduction. Contreras won a Silver Slugger in 2023 and was named an NL All-Star in 2024. He’s averaged over 4 bWAR per year since joining the Brewers and is a legitimate franchise cornerstone. Milwaukee also got two good seasons out of Payamps before he was designated for assignment in 2025. Yeager spent the last three years in the Brewers organization, never making it to the majors. He ended this year with Triple-A Nashville, but elected free agency after the season.

None. While Milwaukee reportedly made headway on a Corbin Burnes deal, that trade didn’t fully come to fruition until February. This year was a weird one, though — the specter of Shohei Ohtani’s free agency hung over these Winter Meetings, leaving teams still in the Ohtani sweepstakes hesitant to commit big money to another player. The Brewers weren’t the only club to sit around and do nothing.

Devin Williams traded to the Yankees for Caleb Durbin & Nestor Cortes

Like the Contreras trade, this happened the week after the Winter Meetings. Since I included the Contreras trade, I feel like I have to include this one, too.

Williams, a two-time NL reliever, is one of the best relievers in (recent) Brewers history. Somehow, the Brewers still won this trade, picking up a scrappy, productive infielder (Durbin) who can play multiple positions and was a huge part of the Brewers’ record-breaking 2025. Meanwhile, Williams struggled in his first season in the Big Apple, losing his closer job in April, and finishing the season with a 4.79 ERA (-0.3 bWAR). Cortes appeared in a handful of games for Milwaukee before being shipped to San Diego in exchange for Brandon Lockridge. Rumors have been flying recently that Williams, a free agent this offseason, could choose to return to Milwaukee as a way to rebuild his value.

Connor Thomas acquired via Rule 5 Draft from the Cardinals

This signing ended up being a nothing-burger for the Brewers. Thomas gave up 12 runs over 5 1/3 innings before being diagnosed with arthritis in his pitching elbow and going on the 60-day IL. He elected free agency after the 2025 season and was signed to a minor league deal by the Atlanta Braves.

Grant Wolfram signed to major league contract

Wolfram had never appeared in the majors, yet Milwaukee signed him to a major league contract on the final day of last year’s Winter Meetings. He was optioned to start the year, but Milwaukee promoted him on April 6. On April 7, Wolfram was both designated for assignment (without having appeared in a game) and traded to the Baltimore Orioles for Daz Cameron. Again, a nothing-burger as far as the Brewers are concerned.

The main takeaway, to me, is that Milwaukee probably won’t acquire anybody (via trade or free agency) unless they feel like it’s a screamin’ deal. Although the Contreras trade looks even better three years later, it was considered a steal by many at the time. Wong had a good last season with Milwaukee but was traded for Winker (who had been an All-Star in 2021) and Toro, who wasn’t far removed from being considered a top prospect (ranked No. 3 in the Astros organization by the end of 2020). The Devin Williams trade felt destined after his blown save against the Mets in the 2024 Wild Card (not to mention his upcoming free agency). The package of Durbin and Cortes didn’t exactly feel like robbery at the time, but Milwaukee is probably very happy they have Durbin after this last season.

On a somewhat related note, there are no swings-and-misses here. Arnold’s transactions during the Winter Meetings have either been low-risk, low-reward (Thomas, Wolfram) or have worked out. If he manages to swing a big trade, I’ll be confident it’s the right move for the Brewers.

Regardless, history points to Milwaukee making at least one deal next week. Let’s see what they end up doing.

Check back on Friday for a rundown of potential trade targets/free agent acquisitions during the Winter Meetings