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  • Chicago Cubs 2024 Offseason Guide: Important Dates, Schedule, & Details

    Brock Beauchamp

    This guide is a comprehensive look at the Chicago Cubs 2023-2024 offseason schedule, including essential dates on the Winter Meetings, MLB Draft Lottery, and dates on which the Cubs will have to make important decisions on their arbitration-eligible players and players with a team or mutual contract options. In the following paragraphs, you will find a list of pending free agents, players with contract options, and a detailed timeline of the MLB offseason.

    Cubs Video

    The 2023 Cubs were full of ups and downs. During the 2023 season, players such as Justin Steele and Adbert Alzolay broke out in a big way. The team was also bolstered by career resurgences from the likes of Cody Bellinger, Kyle Hendricks and Marcus Stroman. Heading into the season’s final month, it appeared the Cubs would make their first postseason appearance since the COVID-19 shortened season in 2020. However, the team collapsed during September, and ended up losing the division to the rival Brewers by 9 games, and finishing 1 game out of a wild card spot. That left a sour taste in many Cubs fan mouths, and that brings us into the 2024 offseason. 

    It looks like it will be a somewhat busy offseason, with likely departures from key 2023 players such as Cody Bellinger and Marcus Stroman. With that being said, many players stepped up and showed why they should be everyday players come 2024, including the debut of Pete Crow-Armstrong, and a very strong 5.0 bWAR season from Nico Hoerner. Enough with all the talk, hopefully the guide below will help give you an idea of what happens through the MLB offseason, featuring many dates and deadlines, along with the significance of them. I hope you enjoy!

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

    2024 Offseason Timeline (detailed explanations following list of dates)

    October 27-November 4: World Series

    5 Days After Conclusion of World Series: League Wide Free Agency Begins (Player/Team/Mutual Options Due, Qualifying Offers also due)

    November 7-9: General Manager Meetings

    November 15: Rule 5 Protection Deadline, Qualifying Offer Decision Deadline

    November 17: Non-Tender Deadline

    December 3-6: Winter Meetings

    December 5: MLB Draft Lottery

    December 6: Rule 5 Draft

    January 2024: BBWAA Hall of Fame Announcement

    January 12: Arbitration Agreement Deadline

    January 29-February 16: Arbitration Hearings

    February 14: Pitchers and Catchers Report

    February 23: First Spring Training Game vs. White Sox

    March 28: Opening Day at Texas Rangers

    World Series
    This one is pretty self-explanatory. The AL Champion Rangers will play the NL Champion Diamondbacks in a seven-game series. When this series is over, the 2024 MLB offseason officially starts. World Series Game 1 is scheduled for October 27, whereas Game 7 is scheduled for November 4 (If necessary.) After the World Series concludes, there is a five-day window where many decisions (Options, Qualifying Offers) must be made before league-wide free agency begins.

    Player/Team/Mutual Options
    Like Qualifying Offers, contractual options must be decided on within five days of the conclusion of the World Series. These options are typically built into the contract when the player signs them. A player option signifies the player's choice to choose whether they would like to exercise the option. If it is a team option, the team can choose if they want to exercise it. On a mutual option, both the team and the player’s side must choose to exercise it. Otherwise, the player becomes a free agent. Often, mutual options do not happen due to the rarity of each side exercising the option. This year, the Cubs will be busy deciding whether they should pick up options or not, as they have 6 players with options this offseason. The players are Marcus Stroman, Kyle Hendricks, Cody Bellinger, Drew Smyly, Yan Gomes, and Brad Boxberger. It is an absolute lock that Cody Bellinger will decline his end of a $12.5 Million mutual option and head into free agency in search of what will likely be a $100+ Million contract after a strong platform season. It also seems that Marcus Stroman will decline his option and forgo his $21 Million salary in 2024 in favor of a longer deal with more guaranteed money. As for Kyle Hendricks, he is facing a $16 Million player option containing a $1.5 Million buyout. After a strong bounceback season, it seems he could opt out and possibly get a larger deal with another club in free agency. However, there is mutual interest in keeping the longest-tenured Cub on the team for the rest of his career. There have also been talks of a possible extension to keep Hendricks in the Windy City for years to come. We will just need to see how this one plays out. It seems like a certainty that the Cubs will exercise their $6 Million option to keep Yan Gomes for another year. Drew Smyly will likely opt into another year with the Cubs for $8.5 Million after a below-average 2023 showing, although he could probably get a similar deal elsewhere as an inning-eater veteran. Lastly, the Cubs will almost certainly decline their end of a $5 Million mutual option with Brad Boxberger in favor of an $800k buyout after seeing him post a 4.95 ERA in only 20 innings in 2023.

    Qualifying Offers
    Like options, Qualifying Offers must be made within five days after the World Series ends. The Qualifying Offer's value typically increases yearly, as it is the average of the top 125 paid MLB players of the previous season. This year, the qualifying offer is slated to be just over $20 million. The Cubs have one surefire Qualifying Offer candidate, and that is Cody Bellinger. Bellinger never received a Qualifying Offer from the Dodgers, making him eligible to receive one now. When the Cubs place a Qualifying Offer on Bellinger, which he will surely decline, they will receive a compensatory pick when he signs with his new team. If he signs with another team, the Cubs will receive a pick after Competitive Balance Round B (after 2nd round) in the 2024 MLB Draft. That will happen regardless of the contract signed by Bellinger, because the Cubs did not pay the Competitive Balance Tax in 2023, and they also do not qualify for Revenue-Sharing, which places them in between both thresholds. If Bellinger resigns with the Cubs, they receive no compensation, but they obviously get Bellinger back. As for Jeimer Candelario, he could have been a possible QO candidate, but since he was traded midseason, that makes him ineligible to receive one. With the Cubs upcoming option decisions on Stroman and Hendricks, that could factor into QO decisions as well. Marcus Stroman is ineligible to receive a Qualifying Offer, even if he declines his player option. First of all, it wouldn’t make any sense for him to take less money, which he would be doing if he accepted a QO instead of exercising his option. Second of all, he already received one when he was heading to Free Agency with the Mets in 2020. Although most of the Qualifying Offers are declined (roughly 10% are accepted) Stroman accepted his in 2020 to return to the Mets for another year. Lastly, Kyle Hendricks could receive a qualifying offer if he declines his player option and no extension is worked out. If Hendricks declines his player option, he will become a free agent. Here is where the Cubs could swoop in with a Qualifying Offer to Hendricks, which would actually signify a $4 Million raise from his option. It would be very possible that Hendricks would accept, and he would spend the 2024 season at Wrigley Field as the longest-tenured Cub.

    Free Agency
    Free agency technically begins the day after the World Series ends. However, during the five days mentioned, the only conversations that can be had are between the free agents and the team they are departing. The Cubs have four free agents this year (Duffey, Greene, Fulmer, Candelario), with the potential to have multiple more through contractual options which are explained above. Naturally, there will be free agents that the Cubs want back, and may make offers to, and others they will let walk. League-wide free agency starts after those five days are over. This could occur as soon as November 5 or as late as November 9, depending on when the World Series wraps up. This is the free agency that the average fan would think of, where any team can contact any player about a possible deal. Most players will sign with a team before Spring Training begins, but it has happened in the past where players have started the season as free agents and signed with teams at the midway point (See Dallas Keuchel 2019 with the Braves.) Free agency continues throughout the offseason and into the regular season, as it never really stops, it typically just becomes more and more picked over.

    General Manager Meetings
    These are typically pretty uneventful for the fans. The General Managers from all 30 MLB Teams meet and discuss possible off-season plans. Here is where some frameworks for offseason trades begin to be talked about. Teams can explore possible paths for their offseason before it gets into full swing.

    Rule 5 Protection
    The Rule 5 Draft is an event that occurs every winter (excluding 2020) as a chance for teams to scout and find possible players who have yet to be given a chance in other organizations. The Rule 5 Draft rules state that teams must protect players who signed at age 18 or younger within five seasons and players who signed at age 19 or older within four seasons. Teams protect players by adding them to their 40-man roster, which can be more difficult in some years due to roster crunches. Players who are not protected by being added to the 40-man roster can be chosen by other organizations during the Rule 5 Draft on December 6 for a $100k fee. Players selected must be kept on the MLB active roster for the whole season or the MLB Injured List when it returns during spring training. Otherwise, if they are designated for assignment and clear waivers, they must be offered back to their original team for $50k. This offseason, there are four Cubs top 30 prospects (via MLB Pipeline) that must be added to the 40 man roster, or otherwise will be eligible to be selected in the Rule 5 Draft. These prospects include Michael Arias (#12), Porter Hodge (#26), Pablo Alienda (#27), and Kohl Franklin (#28). Along with those four ranked prospects, there will likely be more Minor League players protected from the draft. Often these players come from the upper ranks of the minors, as teams believe they have a better chance of sticking on the MLB Active roster for a whole season. Players selected from the Rule 5 Draft do not often become superstars, however, it is not unheard of to find solid role-players. A Cubs-specific example is in 2023, the Mariners selected Chris Clarke from the Cubs during the Rule 5 Draft. Clarke stuck in the Mariners organization until the end of Spring Training, where he did not crack the Opening Day roster. As a result, he was offered back to the Cubs for $50K, and the Cubs accepted. Clarke then pitched the whole 2023 season for the Triple-A Iowa Cubs and posted a 4.90 ERA in 75.1 innings.

    Non Tender Deadline/Arbitration
    Players between 3 and 6 years of MLB service time automatically qualify for arbitration. There is also a system called Super Two, which allows specially selected players with just under three years of service time to qualify for arbitration.  This year, Cubs ace Justin Steele qualified for Super Two status, allowing him arbitration a year early. Arbitration is a system for players on the 40-man roster still under team control to present themselves and attempt to be compensated for what they believe to be fair for their play. If a team doesn’t believe a player is worth their projected arbitration amount, they can choose not to offer them a contract or “non-tender” them. Although only certain players qualify for arbitration, an MLB team can non-tender any player with less than six years of MLB service time, which is an easy way to clear up room on the 40-man roster. Said player immediately becomes a free agent and is available to sign with any team. If the team decides to offer the player a contract before the deadline, they agree to go through arbitration. The teams and players can negotiate a contract until the January 12 deadline. If no agreement is reached, they have to use an arbitrator, who holds an arbitration hearing and sides with either the team or the player. Hearings will be held between January 29-February 16, and pitchers typically go first. As for the hearings, both sides submit their desired pay figures, and the arbitrator uses previous play and other information to decide which figure is more fair. The player is then paid that figure for the year, and no more negotiation on that year’s salary can take place, although extensions can alter that. This can hurt the relationship between the player and the organization; see Corbin Burnes and the Brewers in 2023. 

    Arbitration Eligible Cubs (Expected $ in parentheses)

    • Codi Heuer ($785K)
    • Nick Madrigal ($1.9M)
    • Mike Tauchman ($2M)
    • Nick Burdi ($800K)
    • Julian Merryweather ($1.3M)
    • Patrick Wisdom ($2.6M)
    • Adbert Alzolay ($2.5M)
    • Mark Leiter Jr. ($1.6M)
    • Justin Steele (Super Two - $4.1M)

    Winter Meetings
    Multiple higher-up representatives from each team/organization, along with some agents and players, gather for four days of meetings, which is happening this year in Nashville, Tennessee. This is where trades and free agent signings are discussed and materialized rather than the General Manager Meetings in early November. Just as recently as last year, the Winter Meetings held breaking news, such as when Aaron Judge signed his 9-year, $360 Million mega-deal to stay with the Yankees. This year it could hold the news on where Ohtani will land when he signs a record-breaking contract. If you were going to bet when the most MLB transactions would happen during an offseason, this would be the time to expect.

    BBWAA Hall of Fame Announcement
    This year of Hall of Fame voting does not contain very much excitement pertaining to Cubs fans. There are no players who would be inducted to the Hall of Fame as Cubs that will garner enough support to make it on this ballot. To be inducted, a player needs to receive at least 75% of votes from a group of 389 members from the Baseball Writers Association of America. Alternatively, if a player on the ballot receives less than 5% of the total vote, they are removed from the ballot. The BBWAA ballot is different from the ballot you may have heard of recently. That is the Contemporary ballot and it recognizes Managers, Executives, and Umpires. The last player to be inducted into the Hall of Fame as a Cub by the BBWAA was Lee Smith in 2019. This year, the ballot has a chance to provide new Hall of Famers such as Andruw Jones, Billy Wagner, Adrian Beltre, and possibly Joe Mauer.

    MLB Draft Lottery
    2023 was the first year that the MLB adopted the Draft Lottery. It is a draft system designed to prevent tanking and gives teams a chance to get a higher draft pick than their end of season record would dictate. Only teams that did not make the postseason qualify for the lottery, so the Cubs will qualify this year. Teams with the worst records from the previous year have the highest chance to get the 1st overall pick along with each successive pick, making it a bit similar to how the draft order used to go with the reverse standings. In 2023, the Cubs had a 1.1% chance to get the 1st overall pick, and based on reverse standings should have had the 12th overall pick. After the lottery finished, the Cubs had dropped to #13 in the draft, and that pick saw them take Matt Shaw in July. In 2024, the Cubs have an even lower chance to get the top pick, at 0.4%. Although this pre-lottery order doesn’t indefinitely mean anything, see the Twins jumping up from 13th overall to 5th overall in 2023. The draft lottery just builds suspense for the draft, considering it doesn’t happen for roughly another 7 months after the lottery happens.

    The Rest
    Cubs pitchers and catchers are scheduled to report to Sloan Park, in Mesa, Arizona between February 13-15th (Official date will be announced later), and a couple days after they arrive, the position players will show up, officially opening Spring Training 2024. They will undergo team workouts and practices in preparation for their first Spring Training game on February 23rd against the Chicago White Sox. These Spring Training exhibition matches will continue for roughly a month, and they will bring us into the 2024 MLB season. And finally, on March 28th, your Chicago Cubs are scheduled to take on the Texas Rangers to kick off the 2024 season.

    Thank you for reading and we hope you found it a useful guide. The offseason can be confusing with many dates and deadlines, so we compiled them all into one place for easy viewing. If you have any feedback, please leave a comment in the space below. Have a happy offseason!

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