This guide provides a comprehensive overview of the Chicago Cubs’ 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 Cubs 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 Cubs 40-man roster, view our roster page, updated nightly.

The Chicago Cubs entered the 2025 season with hopes of returning to the postseason for the first time since the shortened 2020 COVID season. They came out strong, surging to a 57-39 first half and establishing themselves as one of the National League’s most balanced teams, ranking among the top 10 in both offense and pitching.

At the plate, the breakout star was Pete Crow-Armstrong, who showcased his all-around talent by completing an impressive 30-30 season, cementing himself as one of baseball’s rising young stars. On the mound, rookie right-hander Cade Horton emerged as a frontline force, posting a 2.67 ERA in 22 starts and giving the Cubs a major boost in their rotation.

The Cubs finished the year with 92 wins — their most since 2018 — and secured the top Wild Card spot in the National League. Their postseason run, however, came to an end in the NLDS, where they fell to the division-champion Milwaukee Brewers in a hard-fought Game 5. Still, 2025 marked a major step forward for Chicago. With a talented young core and newfound momentum, the Cubs will look to build on their success this offseason as they aim to take the next step toward championship contention in 2026.

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

2026 Offseason Dates & Calendar

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.

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 Chicago Cubs, several players are set to reach free agency following the 2025 season, including Taylor Rogers, Ryan Brasier, Michael Soroka, Caleb Thielbar, Drew Pomeranz, and Brad Keller. Each played a role on the pitching staff in 2025, and it remains to be seen which of them the Cubs may look to bring back as they prepare for the 2026 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. For the Chicago Cubs, several key decisions loom that could shape the club’s offseason plans.

Justin Turner holds a $10 million mutual option with a $2 million buyout. Mutual options require both sides to agree to extend the contract, and more often than not, one side declines—typically leading to the buyout being exercised.

The Cubs also hold club options on Andrew Kittredge ($9 million with a $1 million buyout) and Colin Rea ($6 million with a $750,000 buyout). The team will weigh each decision carefully based on performance and roster needs heading into 2026.

Additionally, Shota Imanaga’s contract includes a unique structure that allows the Cubs to exercise a three-year, $57 million extension after the 2025 season, which would bring the total value of his deal to five years and $80 million. If the Cubs decline that club option, Imanaga would instead have a $15 million player option for 2026. His performance and long-term outlook will play a major role in how the team proceeds.

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, 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 team and must never have previously received a Qualifying Offer. Teams have until five days after the World Series ends to extend the offer, and players then have until mid-November to decide whether to accept or decline. If a player rejects the offer and signs elsewhere, their former team receives draft-pick compensation, depending on the club’s market size, revenue-sharing status, and the value of the player’s new deal.

For the Chicago Cubs, there will be no Qualifying Offers issued this offseason. None of their impending free agents — Taylor Rogers, Ryan Brasier, Michael Soroka, Caleb Thielbar, Drew Pomeranz, or Brad Keller — are expected to command a contract near the $22 million threshold, making it unlikely that extending a Qualifying Offer to any of them would be beneficial for the club.

Free Agency

Free agency officially begins the day after the World Series concludes. However, during the initial five-day period, players are only permitted to negotiate with their previous club. Once that window closes, full free agency opens, allowing all 30 teams to contact and negotiate with any available player. Depending on the length of the World Series, league-wide free agency is expected to begin between November 2 and November 6.

As previously noted, several players are set to reach the open market this offseason: Taylor Rogers, Ryan Brasier, Michael Soroka, Caleb Thielbar, Drew Pomeranz, and Brad Keller. Each brings varying levels of experience and depth in the pitching department. The Cubs’ front office will evaluate whether to pursue potential reunions or explore outside additions as they continue to shape the roster for 2026. Free agency will remain active throughout the winter and often extends into spring training as clubs finalize their rosters.

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.

The Rule 5 Draft takes place each winter (with the exception of 2020) and offers every organization a chance to uncover unprotected talent from other clubs. Under Rule 5 regulations, players who signed at age 18 or younger must be protected within five seasons, while those who signed at 19 or older must be protected within four. Teams safeguard eligible prospects by adding them to the 40-man roster — a process that can be challenging when roster space is limited.

For the Chicago Cubs, several prospects will need to be evaluated for protection ahead of the mid-November deadline to avoid exposure in this year’s Rule 5 Draft, scheduled for December 10. Among the players likely to draw consideration for addition to the 40-man roster are Brandon Birdsell, Grant Kipp, and Connor Noland, among others. Each has shown enough development in the minors to warrant discussion as the Cubs front office determines how to best balance depth and roster flexibility.

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

While most Rule 5 selections don’t become stars, the process has occasionally yielded hidden gems. For the Cubs, it represents both a potential risk of losing unprotected talent and an opportunity to uncover an under-the-radar contributor from another organization.

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.

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 Cubs (Expected $ in parenthesis)

Reese McGuire: $1.9 Million

Justin Steele: $6.55 Million

Eli Morgan: $1.1 Million

Javier Assad: $1.9 Million

Each offseason, Major League Baseball announces the Competitive Balance Draft picks, designed to help smaller-market and lower-revenue teams maintain parity across the league. These selections, first introduced in 2012, are awarded annually based on a formula that factors in a club’s market size, revenue, and winning percentage. Eligible teams are placed into one of two rounds: Round A, which occurs between the first and second rounds of the MLB Draft, and Round B, which takes place between the second and third rounds. In addition to the extra draft pick, teams that receive a Competitive Balance selection are also granted a larger international signing pool.

Unlike standard draft selections, Competitive Balance picks can be traded once, though they cannot be exchanged solely for cash considerations.

For the Chicago Cubs, this system generally doesn’t come into play. Due to the team’s large market size and strong revenue base, the Cubs are not typically eligible for Competitive Balance selections and have not received one since 2013. As such, fans shouldn’t expect the Cubs to be among the teams awarded an extra pick when MLB announces the 2026 recipients in early December.

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.

In 2023, Major League Baseball implemented 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 selections in the following year’s draft. While teams with the worst records still have the best chances, the lottery adds an element of randomness to what was once determined strictly by reverse standings.

Because the Chicago Cubs reached the postseason, they are not part of the draft lottery. Instead, their draft position will be determined by the order in which playoff teams are eliminated, along with factors such as revenue-sharing status and regular-season winning percentage. The 12 postseason clubs select in this order: Wild Card Series losers, Division Series losers, Championship Series losers, World Series runner-up, and finally, the World Series champion. Since the Cubs were eliminated in the Division Series, they are projected to hold a late first-round pick in the upcoming MLB Draft.

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.

The international signing period reopens on January 15, giving MLB organizations one of the most important opportunities to acquire young talent from around the globe. While the majority of signings come from Latin America, teams also scout and sign players from Asia, Europe, and other regions. During this window, clubs can reach agreements with foreign players who are 16 years or older. Signing bonuses vary widely — some prospects sign for modest sums and blossom into stars, while others command millions but never reach their potential. The international market remains one of baseball’s most unpredictable talent pipelines.

Each team operates under a hard spending cap, which varies based on market size and other factors. For 2026, the Chicago Cubs fall into the $6,679,200 bonus pool tier. Bonuses of $10,000 or less do not count against this total. Many agreements are reached informally well before the signing date, as teams invest years in scouting and relationship-building with these young players and their families.

While some international signees advance quickly through the minors and reach the major leagues within five or six years, others take longer or never fully develop. The international signing period runs through December 15, after which clubs immediately turn their attention to scouting and preparing for the next class of international talent.

Although official dates have now been announced, Cubs Con is scheduled for January 16–18, 2026, at the Sheraton Grand Chicago. The annual event gives fans the opportunity to meet their favorite players and coaches, collect autographs, and celebrate the start of a new baseball season. It’s a fun, family-friendly tradition that brings Cubs fans together for a memorable weekend of baseball excitement before Spring Training gets underway.

Chicago Cubs pitchers and catchers will report to Sloan Park in Mesa, Arizona in mid-February, with position players arriving a few days later to begin full-squad workouts. Spring Training games in the Cactus League will start shortly thereafter and continue for about a month as the team prepares for the upcoming regular season.

Dates for Chicago’s first Cactus League game and MLB’s Spring Breakout have not yet been announced, but both are expected to take place in the traditional February/March window. The Spring Breakout event will once again showcase each organization’s top prospects in a series of exhibition games against other clubs’ best young talent.

The 2026 MLB regular season is scheduled to officially open on March 25, when the New York Yankees face the San Francisco Giants on Opening Night. Unlike recent years, there will be no international series to begin the season, with all Opening Day games taking place in North America. The Cubs, along with the rest of Major League Baseball, will open their season the following day, marking the official return of baseball 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!