Baseball is a sport that's motivated by deadlines. The Trade Deadline during the season is one example of deadlines spurring action. Front offices want to put off making decisions as long as possible, gathering as much information as they can before they make a final move.
As the offseason unfolds following the conclusion of the World Series, the important dates can be easy to forget and sometimes sneak up on fans.
Let's take a look at the calendar of important dates to know over the course of the Brewers 2023-24 offseason.
Five days after the World Series ends - Free Agency opens, contract option decisions due
Free agency doesn't open in a flurry of deals like it does in the NFL and NBA, which is why this date usually passes in relative obscurity. Teams can sign free agents beginning five days after the conclusion of the World Series, whenever that is. It's not a fixed date until the Fall Classic ends, but early November is when it opens.
The Brewers may not be big buyers on the free agent market this winter, but they could strike early if they see someone they want.
Also, decisions on contract options are due by this time. The Brewers have four players with contract options that need deciding. Andrew Chafin and Justin Wilson seem like obvious declines while Mark Canha and Wade Miley (mutual) are a different story but neither are a guarantee to get picked up.
Qualifying offers have to be extended by this date as well but the Brewers do not have any free agents that are worth the QO this year.
November 14th - Roster Protection Deadline
In order to protect eligible minor league players from the Rule 5 Draft, the Brewers have to add them to the 40 man roster by November 14th at 6 PM ET. While this typically includes top prospects, it doesn't have to. Last year the Brewers added Jon Singleton to the 40 man at this time.
This year, the top eligible Brewers minor leaguers include Jeferson Quero, Carlos D. Rodriguez, Evan McKendry, and Freddy Zamora.
November 17th - Non-tender deadline
The tender deadline or non-tender deadline, depending on your view of a glass being half full or empty, is just a few days later. There's plenty of roster shuffling around this time and if teams want to clear more roster spots for prospects, they could choose to non-tender a few days early, but the Brewers tend to take it down to the wire.
This is where arbitration eligible players learn if they will be "tendered" a contract for next season or if they are "non-tendered" and immediately become a free agent. Players on the bubble tend to settle on a salary on this date. Players whose jobs are secure tend to just get announced as being tendered and they will figure out the salary later.
The Brewers have a couple of non-tender candidates this offseason in Rowdy Tellez and Abraham Toro. Brandon Woodruff's contract status will also be quite interesting to watch at this time given he's likely to miss all of next season, his final season of arbitration.
December 3rd-6th - Winter Meetings, Rule 5 Draft, Draft Lottery
There will be a whole lot of activity during these four days of the annual Winter Meetings, being held this year in Nashville. Every team's front office is in the same building and a lot of moves get made or at the very least the groundwork for future moves in the offseason get made here. Last offseason, the Brewers didn't do much at the Winter Meetings, but they laid the groundwork there that led to the William Contreras trade.
Signings, trades, and especially rumors will be plentiful.
Two more special events are held here, with the MLB Draft Lottery taking place on December 5th. The Brewers will not be participating in the Lottery this year after making the playoffs. Their first round draft pick is already locked in. Then there's the Rule 5 Draft, held on December 6th as the unofficial end of the Meetings.
In the Rule 5 Draft, teams can select minor league players from other organizations for a low sum of cash and place them on their own 40 man roster. Last year, the Brewers selected reliever Gus Varland from the Dodgers and he made the initial roster, but was later sent back to Los Angeles. The Brewers haven't lost a player in the Rule 5 Draft since Miguel Diaz in 2016. There's also a minor league phase.
January 12th - Arbitration filing deadline
For the arbitration eligible players that didn't settle at the non-tender deadline, January 12th is the date that the rest of them usually settle on a salary for the upcoming season. Both sides will try to agree to a number and avoid an arbitration trial. When the deadline passes, both team and player must file for a number. While negotiations can continue all the way up until the trial, which usually happens in February, teams typically discontinue talks after this deadline.
Last year the Brewers couldn't agree to a salary for Corbin Burnes and took him to a hearing, where they won and caused some tension with Burnes in the process. The Brewers should look to avoid that same outcome with Burnes this year.
January 15th - International Signing Period opens
This doesn't impact the major league roster construction at all, but a new international signing window opens on the 15th of January. This is when you'll see teenagers usually from Latin America sign contracts with organizations. The Brewers have been highly successful in this area in recent years, landing players such as Jackson Chourio, Jeferson Quero, Luis Lara, Hendry Mendez, and other top prospects.
Milwaukee usually lands a couple of the highest rated international prospects and fill out the class with a ton of depth, usually around 30 or so players in total.
February 13th-15th - Brewers pitchers and catchers report
The official end of the offseason as pitchers and catchers report. All teams begin their report date in this three day window. The official date hasn't been announced yet but the second week of February is when players show up to camp and preparations for the 2024 season get underway.