This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

As the Rangers celebrate the first World Series triumph in their franchise’s history, the offseason is now officially underway for all of baseball. Here are the dates, names and decision points to know as the Cubs work to assemble a playoff-caliber roster for 2024 and beyond.

What are the key dates?

Thursday (one day after World Series): Eligible players became free agents, beginning a “quiet period” during which that group can negotiate only with their own team. Teams were also once again eligible to make trades.

Monday (fifth day after the World Series): The deadline for teams and players to make decisions on contract options. Also, the “quiet period” ends and Major League free agents are free to sign with any club as of 4 p.m. CT. Minor League players become free agents at 4 p.m. CT, if applicable. This is also the deadline for clubs to tender qualifying offers. 

Nov. 7-9: GM Meetings in Scottsdale, Ariz.

Nov. 14: The deadline for players to accept a qualifying offer is 3 p.m. CT. The deadline to add players to the 40-man roster to protect them from the Rule 5 Draft is 5 p.m. CT.

Nov. 17: Tender deadline. Often referred to as the non-tender deadline, 7 p.m. CT is the deadline by which teams must formally tender 2023 contracts to unsigned players, including their arbitration-eligible players. If a player is non-tendered, he becomes a free agent. 

Dec. 4-6: Winter Meetings in Nashville, including the MLB Draft lottery on Dec. 5 and the Rule 5 Draft on Dec. 6.

Jan. 12, 2024: Eligible players and their teams exchange arbitration figures.

Jan. 15, 2024: Start of the new international signing period.

Who are the Cubs’ free agents?

1B/CF Cody Bellinger, RHP Brad Boxberger, 1B/3B Jeimer Candelario, RHP Tyler Duffey, RHP Shane Greene, RHP Michael Fulmer.

Will any of those players be back in ‘24?

Re-signing Bellinger will be a priority, but it could be a tough task as he looks poised for a lucrative, long-term deal on the open market. The Cubs acquired Candelario at the Trade Deadline last season and it would make sense to try to retain him, given Chicago’s question marks at the infield corners. Fulmer underwent right elbow surgery after the season and could miss all of next year. If Duffey or Greene is back, it would likely be on a Minor League contract. Boxberger endured a disappointing, injury-marred '23, making his place in any plans unclear right now.

Which players have contract options?

1B/OF Cody Bellinger ($25 million mutual option, or $5 million buyout)
RHP Brad Boxberger ($5 million mutual option, or $800,000 buyout)
C Yan Gomes ($6 million team option, or $1 million buyout)
RHP Kyle Hendricks ($16 million pre-bonus team option, or $1.5 million buyout)

Bellinger declined his side of the mutual option and entered free agency, where he will be one of the higher-profile bats available. As expected, the Cubs picked up the options for both Hendricks and Gomes, a source told MLB.com on Sunday. Boxberger had his option declined by the Cubs.

While pitchers Marcus Stroman ($21 million in ‘24) and Drew Smyly ($8.5 million pre-bonus salary) do not have options in their respective deals, they do have the ability to opt out and hit the open market. Sources told MLB.com on Saturday that Stroman made the decision to opt out, which will put him in the free-agent pool.

Will any of the Cubs’ free agents get a qualifying offer?

Now that Bellinger is a free agent, as anticipated, it will be a no-brainer for the Cubs to extend a qualifying offer to the center fielder. This year’s figure is $20.325 million, the average of the top 125 salaries in MLB. It’s the first time the qualifying offer has topped $20 million. By offering a QO, the Cubs would ensure they receive Draft pick compensation if Bellinger were to decline and then sign elsewhere.

Candelario and Stroman (if he were to opt out of his deal) are ineligible for a qualifying offer. Candelario does not qualify due to being traded in-season last year and Stroman is not eligible due to already receiving a QO earlier in his career.

Who is arbitration eligible?

RHP Adbert Alzolay, RHP Nick Burdi, RHP Codi Heuer, RHP Mark Leiter Jr., INF Nick Madrigal, RHP Julian Merryweather, LHP Justin Steele, OF Mike Tauchman, INF Patrick Wisdom.

Are any of those players non-tender candidates?

Burdi and Heuer look like non-tender candidates, given their issues with injuries. Wisdom might be viewed as a borderline non-tender case, but he offers depth at first and third base (positions of need) and could return as a weak-side platoon power bat at a relatively reasonable cost.

What's the payroll situation?

On the Major League active roster, there are five players (OF Ian Happ, 2B Nico Hoerner, OF Seiya Suzuki, SS Dansby Swanson and RHP Jameson Taillon) locked in for ‘24 on guaranteed contracts (worth a combined $97.5 million). When factoring in contract options, players with opt-out clauses, arbitration projections, pre-arb salaries and other expenditures, the projected ‘24 payroll reaches the $170-180 million range.

One question facing the Cubs for ‘24 is whether the team is willing to go over the first Competitive Balance Tax threshold of $237 million. At points of true contention in the past, Chicago has gone over that line. Right now, Spotrac.com estimates that the Cubs have roughly $75 million in CBT space before hitting that first threshold.

Which notable prospects need to be protected from the Rule 5 Draft?

Generally speaking, players who signed with their current club at age 18 or younger and have five years of experience or signed with their current club at age 19 or older and have four years of experience, and are not protected on 40-man rosters, are eligible to be plucked away in December’s Rule 5 Draft. The catch is that the claiming team must keep the player on its Major League roster for the entirety of next year. 

Looking at MLB Pipeline’s Top 30 list for the Cubs, the players eligible for the Rule 5 Draft include: RHP Michael Arias (No. 12), SS Luis Vazquez (No. 21), RHP Porter Hodge (No. 26), C Pablo Aliendo (No. 27) and RHP Kohl Franklin (No. 28). The list of Rule 5 eligible Minor Leaguers is lengthy, but two more names of note for the Cubs are LHP Bailey Horn and OF Yonathan Perlaza.

What are the Cubs’ needs this winter?

Losing Bellinger would create a significant void for both the offense and defense for the Cubs. Both center field and first base would immediately become areas in need of addressing. The North Siders will also be looking for pitching. Those are a few of the big questions facing the Cubs in this important offseason.