Brewers 2024 Winter Meetings: Full Details and Matt Arnold's checklist heading in

Last year, Milwaukee Brewers GM Matt Arnold was the talk of the Winter Meetings. He had just signed uber-prospect Jackson Chourio to a record-breaking eight year, $82 million contract extension prior to Chourio's own MLB debut. Getting that contract done helped kickstart Arnold's run to winning Executive of the Year in 2024.

This year, Arnold might not be the talk of the town, that's going to be Juan Soto. The Winter Meetings figure to be much more active this year than last year's, which was largely a dud outside of the Chourio signing. However, that doesn't mean there's not still plenty of work for Arnold to do.

The Brewers have needs to address, especially with Willy Adames soon to be signing elsewhere and he may even sign at the Winter Meetings. Thus far in the offseason, the Brewers have been quiet. They haven't signed any free agents to the 40 man roster, only completing a handful a minor league contracts with invites to spring training. They've made a couple of expected prospect additions to the 40 man, they non-tendered Hoby Milner, and haven't made a single trade.

Most of the market is likely waiting on Juan Soto to sign, as that will determine who has money left for the other big names on the market and then the trade market and free agency will really kick into high gear. Since Soto is likely to sign during or right before these Winter Meetings, that means Matt Arnold is going to have to be ready to get moving at a moment's notice.

Arnold doesn't like to see this week as "winning the offseason" or "winning the Winter Meetings", because ultimately everything is determined on the field.

Everything Brewers fans need to know about the Winter Meetings: Dates, Full Details

This year's annual Winter Meetings are taking place at the Hilton Anatole hotel in downtown Dallas, Texas. They're slated to be held Monday, December 9th through Thursday, December 12th.

Every team's manager and general manager will take a turn speaking to the assembled media, which will allow fans to gain further insight into what the team is looking for and thinking ahead of next season.

There are three big events on the schedule. First, on Sunday night at 6:30 PM CT, to kick off the Meetings, MLB will announce the results of the Hall of Fame Classic Era Committee ballot.

Then, the 2025 MLB Draft Lottery will take place the night of Tuesday the 10th at 4:30 PM CT. The Brewers are not eligible to win the lottery as they were a playoff team, but the 2025 Draft order will be determined and finalized. The Brewers are slated to have the 20th overall pick.

Finally, the Rule 5 Draft will take place Wednesday afternoon at 1 PM CT. The Brewers will have an opportunity to select a player from a different organization and add him to their 40 man roster if they so choose. They do not have to pick anyone and they are not expected to make a pick.

Big events like press conferences announcing new contracts can be added to the schedule at any time. While the big marquee events of the Winter Meetings may not provide much headline material for the Brewers, if Matt Arnold is able to accomplish these three things, he'll make himself one of the big winners and take some headlines.

#1 - Add a legitimate solution at SS/3B

It's no secret that Willy Adames is not coming back. The question is who do the Brewers get to fill the gap on the left side of the infield. Manager Pat Murphy has said he's inclined to move Joey Ortiz over to the shortstop spot, which would leave an opening at third base.

Incumbent options at third base are Andruw Monasterio, Oliver Dunn, and Sal Frelick. The first two are not starting caliber options and Frelick is a Gold Glove outfielder that, while he could play the position, also doesn't fit the offensive need the Brewers will have at third base to replace Adames' production. Frelick at third base is more of a band-aid than a desirable solution.

How Arnold fills that gap on the left side of the infield is anyone's guess. Free agent options include Alex Bregman, Ha-Seong Kim, Hye-Seong Kim, Josh Rojas, and Yoan Moncada. Bregman is going to be out of Milwaukee's price range, the Kims are unrelated but both are logical fits, could be in the Crew's price range, and can play shortstop, keeping Ortiz at third. Rojas and Moncada are coming off down years but should be plenty affordable with decent upside.

Trade options include Alec Bohm, Coby Mayo, Ryan McMahon, and Jeimer Candelario. Bohm makes a lot of sense for Milwaukee to immediately replace the offensive output of Adames, Mayo fits the mold as a young, controllable player that the Brewers like to get, while McMahon and Candelario have bigger contracts to take on.

There's several more options available to Arnold that aren't named here, but by the end of the Winter Meetings, Arnold is going to want to have checked off the box of getting someone that can realistically be plugged into the starting lineup everyday on the left side of the infield, because he doesn't currently have it on this roster.

#2 - Find a trade partner for Devin Williams

The Brewers can posture all they want that they'll look to keep Devin Williams into the season and re-evaluate at the Trade Deadline if they want to move him in his final year of team control. In all likelihood the Brewers will be competitive in 2025 making a trade of an elite closer a terrible idea in the middle of the season. They made that mistake once before and it's not a mistake the Brewers want to make twice.

Keeping Williams through to free agency is possible, but is that the best use of his value? If the Brewers are going to trade Williams, the best time is now.

There are sure to be a number of teams seeking a dominant All Star closer this offseason that have the ability to pay the Brewers what they want in return. The Phillies, Dodgers, Blue Jays, Diamondbacks, and Rangers are teams that figure to be in the market, though there hasn't been much in hard intel about trade talks with any of these clubs. That's not atypical as the Brewers tend to operate in silence in trade talks.

Matt Arnold could also check these first two boxes at the same time with a trade for Williams supplying the answer on the left side of the infield the Brewers need. Williams plus a prospect for Alec Bohm can be a win-win proposal for both Milwaukee and Philadelphia, for example. Whether it's Bohm or some young, controllable infielder still early in their career, the Brewers would be smart to kill two birds with one stone here.

A Williams trade is sure to make headlines at the Winter Meetings, or whenever it may happen this offseason, but the smart play for Arnold could be to move quickly. The relief pitcher market can move quickly as it usually doesn't involve high dollar figures and teams look to grab the top arms early. For the Brewers to get the best possible return on Devin Williams, they're going to want the most amount of teams possible still needing an elite closer.

Other top names on the relief market include Tanner Scott, Clay Holmes, Jeff Hoffmann, Carlos Estevez, Blake Treinen, and Jordan Romano. Once those players find new teams, that's one potential bidder for Williams that's out of the market.

The more teams that are in the market for a closer, the more likely the Brewers find someone that will give them what they want. Finding a trade partner for Williams should be a priority at these Winter Meetings.

#3 - Pick out an under the radar starting pitching addition

The Brewers aren't going to be able to afford the top of the market starting pitchers. We've seen Luis Severino sign with the Athletics for three years and $67 million. If Severino is pulling that kind of money, even though the A's have to overpay players to get them to sign up to play in Sacramento for the next three years, the pitching market is going to be pricey.

That's what made it all the more surprising to see the Brewers move on from Colin Rea and his reasonable $5.5 million salary for 2025. Finding another player for a comparable salary that they can rely on to eat up innings like Rea did will be difficult.

The Brewers starting pitching depth has taken a hit this offseason as several pitchers are in free agency. Rea, Joe Ross, Wade Miley, Bryse Wilson, and Frankie Montas combined for 59 starts last season. Montas is already gone as he's signed with the Mets on a two year deal.

Milwaukee is going to need to add at least one more starting pitcher this offseason because they truly do not know what Brandon Woodruff can bring next year, Tobias Myers will be hard-pressed to repeat his rookie breakout season, and the final spots are currently slated to be covered by major question marks in Aaron Ashby and DL Hall, plus a number of unproven prospects with no MLB experience.

Finding hidden diamonds in the rough has been a specialty of the Brewers front office in recent years, and Colin Rea was one of those diamonds. Now it's time to find the next one and striking their top target early before too many other teams jump into his market should be a priority for Matt Arnold. The Brewers will have researched each of these free agents and they have an idea on which ones they can help improve and can help this team at an affordable price.

If Matt Arnold can accomplish all three of these things, it will be a successful and winning Winter Meetings. It may not make the national headlines as a winning Meetings, but these are the major roster construction moves Arnold has to make and this is the best time for him to get all of these done.