Milwaukee Brewers: Complete Winter Meetings Preview

JUPITER, FL - FEBRUARY 23: Baseballs and a bat sit on the field of the Miami Marlins during a team workout on February 23, 2016 in Jupiter, Florida. (Photo by Rob Foldy/Getty Images)
JUPITER, FL - FEBRUARY 23: Baseballs and a bat sit on the field of the Miami Marlins during a team workout on February 23, 2016 in Jupiter, Florida. (Photo by Rob Foldy/Getty Images) /

It’s almost here! MLB’s Winter Meetings are just around the corner and this once quiet off-season has started to get a little louder over the past week. Here is a complete preview for what Milwaukee Brewers fans should expect to see at this year’s Winter Meetings.

Milwaukee Brewers General Manager David Stearns will be at the Walt Disney World Swan and Dolphin Resort in Orlando, FL from December 10th through the 14th for baseball’s annual Winter Meetings. Stearns and his staff will join the front offices from every team around the league in traveling to these meetings with hopes to improve their teams for the 2018 season.

These meetings are where the biggest frenzy of activity happens during the MLB off-season. Free agents sign new contracts, players get traded to new teams, and franchises’ futures get altered. It all happens here at the Winter Meetings.

With every front office in baseball gathered in one place, trades can pop up without a moment’s notice. Last year, there was no talk of the Milwaukee Brewers and Boston Red Sox being deep in trade discussions until they announced the deal was completed. It can happen just like that.

Every team goes into these meetings with a list of what they’re looking to add and David Stearns has his list in hand. The list is much shorter than it has been in recent years, but that doesn’t make it any less important. With the rebuild just about complete and the Brewers ready to make the leap to being a perennial contender, Stearns’ decisions this winter will be crucial to the team’s long-term success.

David Stearns’ Shopping List

With Jimmy Nelson’s injury, this addition is vital to the Brewers’ success in 2018. The need for a pitcher went from a back-end addition to a frontline starter. Frontline starters are much more expensive to acquire than back-end additions, unfortunately. There are also fewer options on the market for those types of pitchers. Those who have top of the rotation arms generally prefer to keep them.

In the free agent market, the top arms in Yu Darvish, Jake Arrieta, and Lance Lynn, the contracts they sign will be ridiculously high. It’s not worth spending that kind of money for those pitchers. That leaves the trade market. There are a few teams that are going to begin a rebuilding process that have the frontline starter the Milwaukee Brewers desire. The Kansas City Royals, Tampa Bay Rays, and Detroit Tigers are all beginning a rebuild and have starting pitchers that could interest David Stearns.

Finding a starting pitcher is Stearns’ highest priority this offseason, he said so himself. It should surprise absolutely no one if Stearns leaves these meetings with an ace starting pitcher in tow.

The next priority for the Milwaukee Brewers is finding a permanent solution for the keystone position. Jonathan Villar was thought to be the future of the position after a breakout 2016 campaign. But Villar’s disastrous 2017 season puts his future in question. Eric Sogard came out of the gates hot when he was called up in May. But, he too, regressed hard and forced the Brewers to acquire Neil Walker in August. Walker is now a free agent and seems unlikely to return.

Sogard has re-signed with the Crew on a $2.4 million deal and he provides quality insurance at the position. But something else should be done if the Brewers wish to make the postseason in 2018. A second baseman that can lead off would be an ideal fit. That’s what Villar was in 2016 but if he can’t duplicate that success, the Brewers are lost. That’s why an addition should be made.

The free agent market provides very few options. The trade market, once again, has more options that could suit the Brewers needs. Teams like the Tigers and the Royals, among others, have a second baseman that could be available and of interest to David Stearns.

This is still a need, although not as pressing since there are many options on the relief market right now. One of those options is Anthony Swarzak, whom the Milwaukee Brewers acquired at the July Trade Deadline this year. Swarzak has said he wants to return to Milwaukee and David Stearns is likely open to a reunion, but at the right price.

The trade market for relievers is almost worse than free agency. Bargains can be found more easily for relievers in free agency, whereas trading for a proven reliever can be costly in terms of prospects and contract.

Getting a setup man is the lowest priority for the Brewers right now. It’s not the end of the world if Stearns leaves Orlando without an eighth-inning guy. There will be plenty of arms on the market for Stearns to grab at least one or two.

With David Stearns’ shopping list complete, he’s ready to head to Orlando and talk with his fellow GMs. He may not have any set expectations but Brewers fans might.

What Should We Expect From The Milwaukee Brewers?

One move.

Expect David Stearns to make only one move. No more. No less.

Stearns is entering his third Winter Meetings as the GM of the Milwaukee Brewers. In 2015, he made one move, sending Adam Lind to the Mariners for three young pitchers. In 2016, he made one move, sending Tyler Thornburg to the Red Sox for Travis Shaw, Mauricio Dubon, Josh Pennington, and Yeison Coca.

Each year, he completes one trade and makes a selection in the Rule 5 Draft. The 2015 selection was Colin Walsh, who was later returned, and the 2016 selection was Caleb Smith, who was sold to the Cubs the same day.

All Brewers fans should expect from David Stearns at these Winter Meetings is one trade and a Rule 5 selection. That’s his M.O. and he’s going to stick to his guns. This year, it feels like the Brewers are going to make their one trade at the Meetings a blockbuster. After the success the team enjoyed in 2017, David Stearns could try to make a statement with a blockbuster trade that shakes the foundation of the rest of the league It’s just a feeling, but it makes sense for Stearns to add to his team through a trade rather than free agency. With top of the line starting pitching as his stated priority, any deal for a frontline starting pitcher is considered a blockbuster.

The Rule 5 Draft

On the last day of the Winter Meetings, the Rule 5 Draft occurs. Players that have been in the minor leagues for a certain amount of time without being added to the 40 man roster are eligible to be selected by other teams. Selected players must be kept on a team’s 25 man roster for the entire season or be returned to the original club.

There are a number of pitchers and hitters that could be of interest to David Stearns. Currently, the 40 man roster is at capacity and there is no room for a Rule 5 selection, but a lot can happen between now and December 14th.

The Milwaukee Brewers have the 21st selection in the Rule 5 draft. The Brewers protected each of their four top 30 prospects that were eligible for the draft: Mauricio Dubon, Freddy Peralta, Marcos Diplan, and Jacob Nottingham.

However, there were a few notable names left off the 40 man roster that could very well find themselves with new organizations. Infielder Nate Orf had a good season in Triple-A and could find work in the major leagues as a utility infielder. Also, outfielder Kyle Wren is available to be selected in the draft. He got lost in the shuffle of outfielders that the Brewers possess and is perhaps hoping for a selection in the draft.

What Will Happen?


The Winter Meetings are a five-day extravaganza of baseball activity on a regular basis. But this offseason is different. It’s been slow, to say the least. But now that Shohei Ohtani has chosen a team and a Giancarlo Stanton trade is reportedly complete, teams can make their moves. Free agent signings have begun to pick up over the past few days and GMs are ready to make deals.

With virtually everyone still on the market and no money spent, these Winter Meetings could be one of the most chaotic and frenzied in recent memory. David Stearns is sure to be a part of that chaos. Perhaps he could complete the biggest deal of the meetings. He did that last year with the Thornburg trade until the Red Sox acquired Chris Sale a few hours later.

David Stearns will take his shopping list to Orlando and look for the best deal he can find. He will look for a starting pitcher first and, failing that, he will try to find a second baseman. He may even walk out of Orlando with both of those positions crossed off his list. It is the Winter Meetings after all, nothing should surprise anyone. Let the festivities begin!

Next: It is time for something to happen

This is a pivotal offseason for the Milwaukee Brewers. With the rebuild nearly complete and their window for a championship beginning to open, the right moves can ensure the window of success stays open for as long as possible, while the wrong move, could shut that window early.