Milwaukee Brewers 2026 Offseason Guide: Important Dates, Schedule, & Calendar

This guide provides a comprehensive overview of the Milwaukee Brewers' 2025–2026 offseason, highlighting key dates and events across Major League Baseball’s winter calendar. It includes details on the Winter Meetings, MLB Draft Lottery, and the important deadlines when the Brewers must decide on arbitration-eligible players and those with team or mutual contract options. In the sections that follow, you’ll find a list of pending free agents, players with contract options, and a detailed timeline of the offseason ahead.

To view the current Brewers 40-man roster, view our roster page, updated nightly.

The 2025 season was a dream come true for Brewers fans. Milwaukee didn’t just continue its recent dominance of the National League Central, it elevated the standard entirely. After winning three of the last four division titles entering the year, the Brewers turned in the best regular season in franchise history, finishing 97–65 and pacing all of Major League Baseball in wins. While the offense was steady and opportunistic, it was Milwaukee’s elite pitching and airtight defense that defined this team. The Brewers boasted a top-three starting rotation, a top-ten bullpen, and a top-five defense.

Freddy Peralta anchored the staff with an ace-caliber campaign, while breakout performances from Quinn Priester and Brice Turang gave the club balance and depth. Christian Yelich rediscovered his vintage form, Abner Uribe emerged as a bullpen weapon, and contributions from across the roster turned this group into a powerhouse. Regardless of how October unfolds, 2025 will be remembered as the season Milwaukee reached new heights, a culmination of years of careful roster construction, player development, and steady leadership.

With one of baseball’s most complete rosters and a core still in its prime, the Brewers enter the 2025–26 offseason not looking to rebuild or retool, but to reload for another championship push.

Click any link below to jump to an explanation of that event/date.

2026 Offseason Dates & Calendar

• Oct 24 - Nov 1: World Series
• Immediately After The World Series: Players Become Free Agents, Trade Market Opens
• 5 Days After Conclusion Of World Series: Contractual Options Due, Qualifying Offers Due, League-Wide Free Agency Opens
• Early November: General Manager Meetings
• Nov 13: The MLB Awards
• Nov TBA: Rule 5 Protection Deadline, Qualifying Offer Decisions due
• Nov TBA: Tender Deadline
• Dec TBA: Announcement of Competitive Balance Picks
• Dec 7-10: Winter Meetings (Orlando, FL)
• Dec 10: MLB Draft Lottery
• Dec 10: Rule 5 Draft
• January 2026: BBWAA HOF announcement
• Mid-January: Arbitration agreement deadline
• Jan 15: International Signing Period Opens
• January 2026: Brewers Winter Warm-Up Event
• Late January-Early February: Arbitration Hearings
• Mid-February: Report to Spring Training
• February TBA: First Spring Training Game
• March TBA: MLB Spring Breakout
• March 25: MLB Opening Night (Yankees @ Giants)
• March 26: Opening Day (White Sox @ Brewers)

World Series

Game 1 of the 2025 MLB World Series is set for Friday, October 24, with a potential Game 7 scheduled for Saturday, November 1. The offseason officially begins the moment the final out of the World Series is recorded. Players on expiring contracts immediately become free agents, though certain restrictions apply in the first few days that will be detailed later. The day after the World Series ends, teams can resume making trades for the first time since the midseason deadline — marking the official start of the MLB offseason.

5 Days After The Conclusion Of World Series

As the offseason begins, free agents are permitted to negotiate exclusively with their most recent team for a five-day period. After that window closes, they are free to engage with all 30 MLB clubs.

For the Milwaukee Brewers, two players are slated to reach free agency following the 2025 season. Shelby Miller was acquired from the Arizona Diamondbacks at the 2025 trade deadline but pitched mostly in low-leverage relief situations down the stretch for Milwaukee. Jordan Montgomery was also acquired from the Diamondbacks in the same deal, but after undergoing Tommy John surgery earlier in the year, he never pitched for the Brewers. Both players are set to become free agents after the season.

Player/Team/Mutual Options

During the initial offseason period, teams and players must decide whether to exercise or decline any contractual options for the upcoming year. Several key Brewers contributors hold mutual options that will need to be addressed in the coming weeks, along with a club option for William Contreras.

Rhys Hoskins has a mutual option for $18 million following the 2025 season. If the Brewers decline the option, they will owe Hoskins a $4 million buyout. According to MLB.com’s Mark Feinsand, the expectation is that Milwaukee will decline the option. Brandon Woodruff holds a mutual option for the 2026 season for $20 million, and if it is not exercised by the club, he would receive a $10 million buyout. Danny Jansen’s contract includes a $12 million mutual option, which the Brewers are not expected to pick up, triggering a $500,000 buyout. José Quintana has a $15 million mutual option for next season; should the Brewers decline it, he would receive a $2 million buyout. 

On the club option side, as a part of William Contreras's arbitration last season, he has a $12M club option for 2026 with a $100,000 buyout. The Brewers will certainly pick that up.

Qualifying Offers

Like contract options, Qualifying Offers must be issued within five days of the World Series’ conclusion. The value of the Qualifying Offer changes annually, as it’s based on the average salary of MLB’s 125 highest-paid players from the previous season. For the upcoming offseason, that figure is projected to be $22 million.

To be eligible, a player must have spent the entire previous season with one club and must never have previously received a Qualifying Offer. Teams have until five days after the World Series ends to extend them, and players then have until mid-November to make their decision. If a player declines a Qualifying Offer and signs elsewhere, their former team receives draft-pick compensation. The specifics of that compensation depend on factors such as the team’s market size, revenue-sharing status, and the value of the player’s new contract.

The Brewers offered starting pitcher Brandon Woodruff the qualifying offer, and he accepted. He will return to Milwaukee for one additional year at a $22 million salary.

Free Agency

Free agency officially begins the day after the World Series concludes. However, during the initial five-day period, players can only negotiate with the team they are departing. Once that window closes, full free agency opens, allowing every club to contact and negotiate with any available player. Depending on how long the World Series lasts, league-wide free agency is expected to begin between November 2 and November 6.

As previously mentioned, Shelby Miller and Jordan Montgomery are the only Brewers players who are impending free agents. Free agency continues throughout the offseason and into spring training.

General Manager Meetings

Roughly a week after the World Series concludes, all 30 general managers gather for meetings to discuss league business and key offseason matters. While these sessions don’t typically draw much attention from fans, they often help establish the groundwork for trades and other transactions that take place later in the winter.

Rule 5 Protection/Draft

The Rule 5 Draft takes place each winter (with the exception of 2020) and gives teams a chance to uncover unprotected talent from other organizations. Under Rule 5 rules, players who signed at age 18 or younger must be protected within five seasons, while those who signed at age 19 or older must be protected within four seasons. Teams protect these players by adding them to the 40-man roster, which can be a challenge in years when roster space is limited.

For the Milwaukee Brewers, several prospects will be under consideration for protection ahead of the mid-November deadline to avoid exposure in this year’s Rule 5 Draft, which is scheduled for December 10. That group includes Coleman Crow, Ernesto Martinez, Ethan Murray, and Freddy Zamora, among others.

There will be added intrigue surrounding this year’s process after the Brewers left Shane Smith unprotected last offseason, a move that proved costly when he was selected by the Chicago White Sox and went on to become an All-Star in 2025.

Players who are not added to the 40-man roster by the deadline can be selected by another organization for a $100,000 fee. Any player drafted must remain on the selecting team’s active Major League roster (or the MLB injured list) for the entire season. If the player is designated for assignment and clears waivers, they must be offered back to their original team for $50,000.

While most Rule 5 selections don’t become stars, many develop into useful role players, a reminder of how impactful roster protection decisions can be for a club’s long-term depth.

The MLB Awards

The MLB Awards return to Las Vegas on November 13, taking place at The Chelsea at The Cosmopolitan of Las Vegas. 

Among the honors announced will be the Hank Aaron Awards, Comeback Players of the Year, Mariano Rivera and Trevor Hoffman Relievers of the Year, the Edgar Martínez Outstanding Designated Hitter of the Year, and the All-MLB First and Second Team selections. Around the same time, the BBWAA Awards, including Rookie of the Year, Manager of the Year, Cy Young, and Most Valuable Player, will also be revealed.

Non-Tender Deadline & Arbitration

Players with between three and six years of MLB service time automatically qualify for salary arbitration. There’s also the Super Two designation, which allows a select group of players with just under three years of service to become eligible as well. Arbitration gives players still under team control a chance to argue for compensation they feel reflects their on-field performance. If a team believes a player’s projected arbitration salary exceeds their value, they can non-tender the player instead of offering a contract. Although arbitration eligibility depends on service time, any player with fewer than six years in the majors can technically be non-tendered. Doing so immediately makes them a free agent, while also freeing up a spot on the 40-man roster. Teams have until the non-tender deadline (typically in late November) to decide whether to offer contracts to arbitration-eligible players. Once tendered, the two sides can continue negotiating a salary until mid-January. If no agreement is reached, the case proceeds to an arbitration hearing, where both sides submit salary figures, and a neutral arbitrator selects one. Hearings usually take place between late January and mid-February, with pitchers often going first due to their earlier Spring Training report dates.

The arbitrator’s ruling is final, and the player is paid that amount for the upcoming season. While the process ensures fairness, it can sometimes strain relationships between players and teams

Arbitration Eligible Brewers (Expected $ in parenthesis)

• Jake Bauers: $2MM
• Andrew Vaughn: $7.8MM
• William Contreras: $11.1MM (Brewers hold a $12MM club option with a $100K buyout)
• Nick Mears: $1.6MM
• Trevor Megill: $4.2MM
• Garrett Mitchell: $1MM
• Brice Turang: $4.4MM

Competitive Balance Draft Picks

Each offseason, Major League Baseball announces the Competitive Balance Draft picks, which are designed to help smaller-market and lower-revenue teams maintain competitive balance across the league. These picks were first introduced in 2012 and are awarded annually based on a formula that considers a club’s market size, revenue, and winning percentage. Eligible teams are assigned to one of two rounds: Round A, which takes place between the first and second rounds of the MLB Draft, and Round B, which falls after the second round but before the third. In addition to the extra pick, teams receiving a Competitive Balance selection also get a slightly larger international bonus pool to use during the international signing period.

Unlike other draft selections, Competitive Balance picks can be traded once, though they cannot be exchanged solely for cash considerations. Last season, the Brewers had a Competitive Balance A round pick at #33 overall in the 2025 MLB Draft that they traded to the Boston Red Sox for Quinn Priester.

Winter Meetings

Each December, high-ranking executives from all 30 organizations, along with agents, players, and media members, gather for the MLB Winter Meetings, a four-day event that serves as the centerpiece of the offseason. This year’s meetings will take place in Orlando, Florida, from December 7 to 10. The Winter Meetings are where the bulk of offseason business takes shape. Trades, free agent signings, and major rumors often dominate the headlines during this stretch. Juan Soto, who was the central story of the 2023 Winter Meetings when he was traded to the Yankees, once again stole the spotlight this year after signing a 15-year, $765 million contract with the New York Mets. He was joined in the headlines by Max Fried, who signed with the New York Yankees, and Garrett Crochet, who was traded to the Boston Red Sox in one of the biggest deals of the week.

If there is one point on the calendar when the most MLB transactions are likely to occur, this is it. In addition to roster moves, both the MLB Draft Lottery and the Rule 5 Draft take place during the Winter Meetings, adding even more intrigue to one of baseball’s busiest weeks of the year.

MLB Draft Lottery

In 2023, Major League Baseball introduced a draft lottery system designed to discourage teams from intentionally losing games to secure higher draft positions. Under this system, all clubs that miss the postseason are assigned odds to land one of the top six picks in the following year’s draft. The teams with the worst regular-season records still have the best odds, but the process now includes an element of chance rather than relying solely on reverse standings.

The draft lottery is not of much interest to the Brewers, as postseason teams are not included in the lottery. The order of the postseason teams in the draft is determined by when they get eliminated, revenue-sharing status and then winning percentages. Those 12 teams will choose in the following order: Wild Card Series losers, Division Series losers, Championship Series losers, World Series loser, World Series winner. Within each of those groups, clubs will be sorted by revenue-sharing status, with payee clubs selecting before non-payee clubs.

BBWAA HOF Announcement

Every January, the Baseball Writers’ Association of America (BBWAA) announces its voting results for the newest class of the Baseball Hall of Fame. Players become eligible five years after retirement and can remain on the ballot for up to ten years, provided they continue to receive at least five percent of the vote each cycle. Earning election requires appearing on 75 percent of submitted ballots. If a player falls below the five-percent threshold, they are removed from future ballots and can only be reconsidered later by one of the Hall’s era-based committees. This year’s ballot lacks top-end HOF candidates but still showcases several notable names, including Cole Hamels and Ryan Braun, who are making their first appearance, and Manny Ramírez, who is entering his final year of eligibility.

2026 International Signing Period Opens

The international signing period reopens on January 15, marking one of the most important avenues for MLB organizations to acquire young talent from around the world. Most of these signings come from Latin America, though teams also scout and sign players from Asia and other regions. During this window, clubs can reach agreements with foreign players who are 16 years or older. The range of signing bonuses varies widely. For instance, Ronald Acuña Jr. signed with the Braves for just $100,000 in 2014 and developed into one of the best players in baseball, while highly touted prospects such as Kevin Maitan, who signed for $4.25 million that same year, never panned out. These examples show how unpredictable this market can be.

Each team operates under a hard spending cap, and this year, the Brewers fall into the second-highest bonus pool, with $7,357,100 available to spend. Bonuses of $10,000 or less do not count against that total. Many of these deals are informally agreed upon well in advance, as teams scout and build relationships with players years before they are eligible to sign. While some of these teenage prospects eventually rise through the minors and reach the big leagues within five or six years, many do not. Development paths differ drastically, as players mature physically, adapt to professional baseball, and adjust to entirely new environments. The international signing period officially runs through December 15, after which preparations begin for the next year’s class.

Brewers Winter Warm-Up

Although official dates have not yet been announced, this event typically takes place in January. It gives fans a chance to meet their favorite players, collect autographs, and get excited for the upcoming baseball season. It’s always a fun and memorable way to kick off the year for Brewers fans.

Spring Training 2026!

Brewers pitchers and catchers will report to the American Family Fields of Phoenix in mid-February, with position players arriving a few days later to begin full-squad workouts. Spring Training games will begin shortly after and continue for about a month as the team prepares for the regular season. Dates for the Brewers’ first Cactus League game and MLB’s Spring Breakout have not yet been announced, but both are expected to take place in the usual February/March timeframes. Spring Breakout will once again showcase each club’s top prospects in special exhibition matchups against other organizations’ best young talent.

The 2026 MLB regular season will officially begin on March 25, when the New York Yankees face the San Francisco Giants on Opening Night. Unlike the past few seasons, there will be no international series to open the year, with all games beginning in North America. Every team, including the Brewers, will open their seasons the following day after as baseball returns in full force.

Thank you for reading, and I hope this guide helped make sense of the many dates and details that come with the MLB offseason. It can be a lot to keep track of! I’ll continue to provide updates as more specific information becomes available. Enjoy the offseason, and here’s to a great 2026 season ahead!