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.

CHICAGO -- The Cubs did not meet their goal of reaching the playoffs last season, making this a critical offseason for the ballclub. Here are the key dates, names and decisions to know as the North Siders attempt to build an October-caliber roster for 2025.

What are the key dates?
First day after the World Series: Eligible players become free agents. That starts a five-day “quiet period” in which free agents may negotiate only with their own team. Also, the trade freeze is lifted and Major League players may be traded between clubs.

Fourth day after the World Series: Last date to request waivers on Draft-excluded players until next spring.

Fifth day after the World Series: The deadline for teams and players to make decisions on contract options, the deadline for clubs to reinstate all players on the 60-day injured list, and the deadline for clubs to tender qualifying offers. 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.

Nov. 4-7: GM Meetings in San Antonio.

Nov. 19: The deadline for players to accept a qualifying offer is 3 p.m. CT, and the deadline to add players to the 40-man roster to protect them from the Rule 5 Draft is 5 p.m. CT.

Nov. 22: Tender deadline. By 7 p.m. CT on the Friday before Thanksgiving, teams must formally tender contracts to unsigned players for the following season, including their arbitration-eligible players. If a player is non-tendered, he becomes a free agent.

Dec. 9-11: Winter Meetings in Dallas, including the MLB Draft lottery on Dec. 10 and the Rule 5 Draft on Dec. 11.

Dec. 15: End of the 2024 international signing period.

Jan. 10, 2025: Eligible players and their teams exchange arbitration figures.

Jan. 15, 2025: Start of the new international signing period.

Jan. 17-19, 2025: Cubs Convention at the Sheraton Grand Chicago.

• Full guide to offseason dates, rules, terms

Who are the Cubs’ free agents?
The Cubs’ only two free agents heading into the offseason are starter Kyle Hendricks and reliever Jorge López.

Will any of the free agents be back in 2025?
While Hendricks -- the last remaining piece of the 2016 World Series team -- is revered for his leadership and work ethic, the ‘24 season was likely the end of the line for his stellar tenure with the Cubs. Hendricks wants to keep playing in ‘25, but even the pitcher said at season’s end that his next pitch would likely be with a new team.

López, 31, was a mid-season pick-up for the Cubs after a rough departure from the Mets, playing a key role in turning Chicago’s bullpen around down the stretch (2.03 ERA in 24 games). Given Chicago’s need for relief help this winter, López could remain on the radar.

Which players have contract options?
Cody Bellinger has the ability to opt out of his three-year, $80 million deal this winter. He has a $27.5 million player option (or $2.5 million buyout) for 2025, and then another option ($25 million or $5 million buyout) for ‘26. While nothing is set in stone, the general belief is that Bellinger will opt out and hit the free-agent market again this winter.

Veteran lefty Drew Smyly has a $10 million mutual option (or $2.5 million buyout) for next season, and the expectation is that he will enter free agency.

Will any Cubs get a qualifying offer?
The Cubs do not have any players expected to receive a QO (valued at $21.05 million for the 2025 season). Bellinger received one last year after becoming a free agent, rendering him ineligible for a QO in future seasons.

Which Cubs players are eligible for arbitration?
The Cubs’ list of arb-eligible players this offseason includes catcher Christian Bethancourt; infielders Nick Madrigal, Isaac Paredes, and Patrick Wisdom; outfielder Mike Tauchman; right-handers Yency Almonte, Adbert Alzolay, Colten Brewer, Jimmy Herget, Julian Merryweather, Nate Pearson, Keegan Thompson, and Trey Wingenter; and lefty Justin Steele.

Are there any non-tender candidates from that group?
Everyone except Paredes, Pearson and Steele is a non-tender candidate to varying degrees.

What’s the Cubs’ payroll situation?
The Cubs have six players (Ian Happ, Nico Hoerner, Shota Imanaga, Seiya Suzuki, Dansby Swanson, and Jameson Taillon) locked in on guaranteed contracts for 2025 at a total cost of $111 million. Even factoring in other costs (pre-arb players, the arb class, performance bonuses, etc.), Chicago will have plenty of payroll flexibility to target its needs this winter. Cubs payrolls in recent years have tended to sit right around the first Competitive Balance Tax threshold (set at $241 million for ‘25).

Do any notable prospects need to be protected from the Rule 5 Draft?
Looking at MLB Pipeline’s Top 30 list for the Cubs, players eligible for the Rule 5 Draft this year include outfielder Owen Caissie (No. 2 and No. 34 on Pipeline’s Top 100 list), catcher Pablo Aliendo (No. 13), outfielder Christian Franklin (No. 22) and infielder Ben Cowles (No. 29).

What are the Cubs’ needs this offseason?
Even with a promising second-half from Miguel Amaya, and prospect Moises Ballesteros (Pipeline’s No. 4 Cubs prospect and No. 44 on the Top 100) coming soon, expect the Cubs to be in the market for catching help this offseason. Depending on Bellinger’s decision, Chicago could also use an impact bat (corner outfield or designated hitter being the best path).

On the mound, the Cubs will be looking for at least one starter to add to a rotation featuring Steele, Imanaga, Taillon and Javier Assad. The bullpen will also be in need of reinforcements. The key for Chicago will be to add to the volume of relief options, given the in-season needs that came up throughout 2024.