Chicago Cubs Offseason FAQs, Free Agency, Arbitration, Dates to Remember

The Chicago Cubs failed to make the 2023 postseason, which means they can get started on the offseason a little earlier than some other teams.

The Cubs have a significant to-do list, not the least of which is trying to hang on to their top offseason acquisition, Cody Bellinger. They have several players who are pondering exercising options, including pitcher Marcus Stroman. Plus, they may have some prospects they need to find a way to protect in the Rule V Draft.

Need to get ready for the Cubs hot stove this offseason? Our FAQ on the offseason walks you through it all.

November TBA

Last day for club to make a qualifying offer to an eligible former player who became a free agent, fifth day after World Series, 5 p.m. EST.

The day after the World Series ends, the work begins. The Cubs have five days to tender qualifying offers to potential free agents.

So who qualifies for the Cubs? Three players are free agents — third baseman Jeimer Candelario, pitcher Michael Fulmer and pitcher Shane Greene.

Candelario reveals one the quirks in the QO. Because the Cubs acquired him via trade during the season, they cannot give him the QO. Free agents that have changed teams during the season cannot get a QO.

From there, the Cubs have five players that have options that could allow them to hit free agency — pitcher Marcus Stroman (player, $21 million), Bellinger (mutual, $12 million), pitcher Kyle Hendricks (team, $16 million), catcher Yan Gomes (team, $6 million) and pitcher Brad Boxberger (mutual, $5 million).

It’s widely believed that Bellinger won’t trigger his portion of the option, allowing him to hit free agency. It’s possible that Stroman doesn’t exercise his option, either. In that case, the Cubs could give one the QO.

This year, the qualifying offer is approximately $20.5 million, which is a one-year offer. It is the mean of the league’s top 125 salaries.

Teams make the qualifying offer to prospective free agents in case they lose them because they’ll receive draft pick compensation, either after the first round or after competitive-balance round B.

Last offseason, 14 players were tendered a one-year qualifying offer worth $19.65 million. Two players — Rangers left-hander Martín Pérez and Giants outfielder Joc Pederson — accepted.

Historically, players don’t accept the QO. Since the QO became a thing in 2012, only 12 players of the 124 players offered the QO have accepted, per the New York Post.

Free agents can receive the qualifying offer. If a free agent has previously been tendered a QO, they cannot be tendered another one. Free agents that have changed teams during the season cannot get a QO.

Once a player gets an offer, he has a week to consider it. During that time he can talk with other teams and solicit interest to help them make a decision. But the deadline to accept is Nov. 14 at 4 p.m. EST.

Nov 7-9 — General managers meetings, Scottsdale, Ariz.

The Cubs brass, including president of baseball operations Jed Hoyer, will be in Scottsdale for these annual meetings. Don’t expect a lot of league business to be conducted during these meetings. But many team leaders will start laying the groundwork for free agency and trades during these meetings.

Nov. 17 — Last day for teams to offer 2024 contracts to unsigned players on their 40-man rosters.

Any players not under contract for 2024 must either sign a deal with their current team or they can hit free agency. Most of the big names have either made their decisions or signed with their current teams by this point.

Dec. 3-6 — Winter meetings, Nashville, Tenn.

This is it. MLB’s biggest offseason meeting. Everyone is there — owners, general managers, agents and media. Big deals tend to get done here or get done shortly after everyone departs. Everything is on the table, including free-agent contracts and trades.

Dec. 3 — Hall of Fame Contemporary Baseball/Managers-Umpires-Executives Committee vote announced, Nashville, Tenn.

If you’re into getting your favorite retired manager, umpire and executive whose greatest contributions to the game were realized from the 1980-present era then this is your day. The finalists will likely be announced in advance of the selections, which is done by a 16-member committee and not the wider voting bloc of the Baseball Writers Association of America.

Dec. 5 — 2024 amateur draft lottery, Nashville, Tenn.

MLB will determine the draft order of the non-playoff teams in the 2024 MLB Draft through a weighted lottery system, similar to the NBA Draft Lottery. MLB began using the system last year. Oakland, Kansas City and Colorado each have the best chance of securing the No. 1 pick when the lottery is held.

The Cubs have a 0.4 percent chance of getting the first overall pick through the lottery (but as they say, “So you’re telling me there’s a chance?”). If the percentages hold, the Cubs would end up with the No. 17 overall selection.

Dec. 6 — Winter meeting draft, Nashville, Tenn.

Don’t recognize this? You probably know it better as the Rule 5 Draft. Before the draft, each team must determine which of its non-40 man roster players need to be added to its 40-man roster. This includes:

Players signed at age 18 or younger that have not been added to the 40-man within five seasons of becoming a pro. Players who signed at age 19 or older need to be protected within four seasons.

Thecubreporter.com has a solid list of the Cubs prospects that could end up being protected, or unprotected, for Rule 5 purposes. Three that could interest other teams are pitchers Kohl Franklin, pitcher Porter Hodge and infielder Chase Strumpf.

Players moved to a 40-man roster cannot be drafted. Players that are not moved can be drafted. The draft order is in reverse order of standings. There is a Major League portion (the portion that most fans pay attention to) and a minor league portion.

For teams that draft a player in the Rule 5 Draft, they must pay $100,000 to the player’s club, put him on their 26-man roster immediately and put him out outright waivers if they release him the following season. If he clears waivers, he goes back to his former team for $50,000.

In other words, if you select a player in this draft your team believes that player is ready to help them in 2024.

Last year the Cubs didn’t draft a player in the MLB portion of the Rule 5 Draft. But they selected a few in the minor-league portion, including pitcher Nick Burdi.

The Cubs made one of the more famous Rule 5 picks in 2006 when it drafted Josh Hamilton away from the Tampa Bay Rays. But, the Cubs actually conveyed Hamilton to the Cincinnati Reds for $100,000. Hamilton eventually became an All-Star and MVP with the Texas Rangers.

Dec. 15 — International signing period closes, 5 p.m. EST.

If MLB teams have any international signing money left over for 2023, this is the deadline to spend it.

In January, the Cubs signed Derniche Valdez, the No. 6 overall prospect on the international top 50 list for $2.7 million. They also signed two other Top 20 international players, Ludwing Espinoza and Angel Cepeda, for $1 million each, as part of their international signing pool of $5.284 million.

2024

Jan. 12 — Salary arbitration figures exchanged.

Perhaps the least fun part of the offseason. For players that are salary arbitration eligible, this is the deadline for teams and players’ agents to exchange numbers. Players who have three or more years of Major League service but less than six years of Major League service are eligible. Most teams and players try to reach agreement on a contract before the arbitration deadline, as the process can become acrimonious.

The following players are arbitration eligible — Codi Heuer, Nick Madrigal, Mike Tauchman, Nick Burdi, Julian Merryweather, Patrick Wisdom, Adbert Alzolay, Mark Leiter Jr. and Justin Steele.

If the Cubs have to go to arbitration with any of their players, those hearings will be held between Jan. 29-Feb. 16 in Scottsdale, Ariz.

Jan. 15 — International signing period opens, 9 a.m. EST.

The 2024 international signing period begins. Players eligible to be signed are Player resides outside of the United States, Canada or Puerto Rico and has not been enrolled in high school in any of those locations within the past calendar year. The player is at least 16 years of age or will turn 16 years of age prior to Sept. 1 of the current signing period.