Key dates for Milwaukee Brewers fans to watch out for in the 2025-26 offseason

The MLB regular season is a grueling six-month journey, during which teams only have back-to-back days off when the midseason All-Star Break rolls around in the second week of July. To extend past that six-month season with appearances in seven of the last eight postseasons is therefore not only a testament to the Milwaukee Brewers' commitment to sustained success, but also a feat that is worthy of praise simply due to the taxing nature of the baseball season.

Now, after one of the most memorable seasons in franchise history, the Brewers' offseason has begun, and with it comes a whole new set of challenges. From deciding which players have earned the opportunity to return next season, to weighing the advantages and disadvantages of trading away their ace, to fighting over salaries in the ever-contentious arbitration hearings, the Brewers' front office has a daunting offseason ahead of them.

Tasked with meeting the expectations set by the back-to-back-to-back NL Central division champions who were one of the final four teams remaining in the postseason in 2025, while adhering to the restrictions of the club's modest payroll, and keeping an eye on the future to ensure a prolonged period of losing doesn't surface, President of Baseball Operations Matt Arnold and his excellent assembly of front office employees have their work cut out for them this winter.

It all starts when the World Series, a matchup of either the Seattle Mariners or Toronto Blue Jays and the mighty Los Angeles Dodgers, concludes, which could happen as early as October 28 or as late as the first of November. From there, the MLB offseason officially kicks off, and a franchise-altering trade could happen at any moment. Here are some other dates to watch out for this offseason.

Key offseason dates for Milwaukee Brewers to watch out for

The day after the World Series concludes: eligible players officially become free agents

Whether it is October 29 or November 2 or somewhere in between, the day following the conclusion of the World Series is when eligible players officially become free agents. At this point, players can begin officially signing new contracts with teams. While some players, such as Nate Pearson who just agreed to a contract with the Houston Astros for the 2026 season, will agree to terms with new teams prior to the end of the World Series, they can't officially sign with said team until five days after the Fall Classic ends.

Just two players on the Brewers’ current roster are true free agents at the official end of the 2025 season (others will become free agents after their mutual options are declined), and neither played a major role in the team's 2025 success. Shelby Miller and Jordan Montgomery, the two pitchers that the Brewers acquired from the Arizona Diamondbacks at the trade deadline, are the only two rostered Brewers who will immediately become free agents upon the completion of the World Series.

Five days after the World Series ends: free agents can officially sign with new teams, qualifying offers due

As previously mentioned, a player is not allowed to sign with a new team until five days after the World Series ends, of which the exact date is yet to be determined. Players are allowed to re-sign with their current clubs, but in the Brewers’ case, it's highly unlikely that either Miller or Montgomery secures a contract with Milwaukee that early in the offseason.

Five days after the World Series is also the date at which qualifying offers are due. In brief, qualifying offers are a one-year contract, at a price that is determined by the average of the league's 125 highest-paid players' salaries, which is set at $22.025 million this year. The only players eligible to receive a qualifying offer are those who have never received one in their career and spent the entire last season with the organization that they ended the season with, meaning midseason acquisitions are ineligible. If teams extend a qualifying offer to a player, and they reject it and subsequently sign a free agent contract elsewhere, the offering team receives a draft pick with the size of the contract the player signed determining the position of said pick.

November 18: deadline for players to accept qualifying offers

Brandon Woodruff is the only player that makes any sense for the Brewers to extend the qualifying offer to, and even he isn't a perfect fit. Woody holds a $10 million buyout for the mutual option included in his contract, meaning after he inevitably declines the option, if the Brewers were to then extend him the qualifying offer, they would essentially be offering him $32.025 million to remain with the club for the 2026 season. Despite the Brewers and their fans’ love for Woody, that's a lot to invest in one player for the cash-strapped Brew Crew.

November 21: tender/non-tender deadline

By November 21, teams have to decide whether or not they will tender each player that is under team control, but not signed to a guaranteed deal, a contract for the 2026 season. Any player with less than six years of service time who hasn't been offered a contract extension is eligible to be non-tendered prior to the November 21 deadline, but the move is generally reserved for players whose projected arbitration salaries seemingly outweigh the value that they offer to the team.

The Brewers have seven players currently on their roster who are arbitration eligible this season: Jake Bauers, Andrew Vaughn, Trevor Megill, William Contreras, Nick Mears, Garrett Mitchell, and Brice Turang. Of the group, most are expected to be tendered contracts for the 2026 season, with Bauers and his projected salary of $2 million being the only one who could potentially be a non-tender candidate.

December 8-11: MLB Winter Meetings

The MLB Winter Meetings are a gathering of front office executives and other representatives from each team, during which many trades and free agent signings occur. It was during the Winter Meetings that Milwaukee gave Jackson Chourio his record-breaking contract in 2023 and where the groundwork was laid for the William Contreras trade back in 2022. As such, fans have come to expect some degree of excitement during these four days in the beginning of December, and at the very least it serves as an opportunity to hear Matt Arnold's thoughts halfway through the offseason, as interviews are conducted constantly throughout the weekend.

December 10: MLB Rule 5 Draft

The Rule 5 Draft serves as an opportunity for teams to add players from other organizations without having to trade players of their own. There's a lot of nuance involved in who is eligible for the Rule 5 Draft and the roster restrictions that players face if they are added to a new team, but it essentially works as a way to give older minor leaguers who have yet to debut a chance with a new organization that may be a better fit for them.

A season ago, the Brewers notably lost Shane Smith in the Rule 5 Draft to the Chicago White Sox. Smith went on to become an All-Star in 2025, while the Brewers' Rule 5 selection, Connor Thomas, missed most of the season with an unfortunate elbow injury. Given the Brewers' emphasis on roster flexibility, it's rather shocking that they've elected to be so active in the Rule 5 Draft, which essentially forces a team to roster a player throughout the season without having the luxury of sending him down to Triple-A. Even still, it remains an opportunity to add exciting young talent to their organization without having to give up any prospect capital.