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When the World Series ends later this week, the Cardinals can finally get to work on what may be their most critical offseason rebuild in decades.

Plenty of key dates and decisions are on the horizon for a Cardinals franchise looking to upgrade a roster that slumped to 71-91 this past season. Here’s what to expect over the next few weeks and months:

What key dates are ahead?
First day after the World Series ends: Teams can trade MLB players, and qualifying players become free agents. MLB’s “quiet period,” a time when free agents can negotiate only with their own teams, also begins.

Fifth day after the World Series ends: Teams and players must make decisions on contract options by this date. Also, MLB’s “quiet period” ends, and big league free agents can begin signing with clubs 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: Players have until this day at 3 p.m. CT to accept qualifying offers. Teams have until 5 p.m. CT to add players to the 40-man roster to protect them from being plucked in the Rule 5 Draft.

Nov. 17: Tender deadline: The glass-half-empty name for this date is the “non-tender deadline,” which hits at 7 p.m. CT. Teams must tender contracts to unsigned players, including their arbitration-eligible players. If a player is not tendered, he becomes a free agent.

Dec. 4-6: MLB Winter Meetings: Nashville, Tenn., will become the epicenter of the baseball universe over three days, and the events will include the MLB Draft Lottery on Dec. 5 and the Rule 5 Draft on Dec. 6. The Cardinals, owners of MLB’s fifth-worst winning percentage, have an 8.3 percent shot at winning the No. 1 pick in the lottery. 

Jan. 12, 2024: Arbitration-eligible players and their teams exchange proposed salary figures.

Jan. 15, 2024: This opens the new international signing period.

February 2024: The Cards have yet to finalize the date when pitchers and catchers will report to Jupiter, Fla., for Spring Training, but it should fall around the middle of the month.

Who are the Cardinals' free agents?
RHP Drew VerHagen, RHP Casey Lawrence, RHP Jacob Barnes, LHP Andrew Suarez, INF Juniel Querecuto.

The Redbirds took much of the steam out of this one by trading lefty Jordan Montgomery, former ace Jack Flaherty and former closer Jordan Hicks -- free agents by this time next week -- before the MLB Trade Deadline.

VerHagen has mostly struggled through two injury-filled seasons. Lawrence, Barnes, Suarez and Querecuto opted for free agency rather than being outrighted to Triple-A Memphis.

The Cards' 40-man roster stands at 34 and could climb to 39 after Dylan Carlson (ankle surgery), Brendan Donovan (elbow surgery), Guillermo Zuniga (forearm strain), Wilking Rodríguez (shoulder surgery) and Packy Naughton (elbow surgery) are taken off the 60-day injured list. VerHagen will come off that 40-man roster when he becomes a free agent. 

Who is arbitration-eligible?
Tyler O’Neill and Dakota Hudson are eligible for their final rounds of arbitration, while Tommy Edman, Ryan Helsley and Andrew Knizner will be arbitration-eligible for a second time. Carlson, John King and Jake Woodford will hit arbitration for the first time.

O’Neill has suffered through two injury-filled seasons following his career year in 2021, but the Cardinals will likely tender him a contract because they still believe he can be their everyday left fielder. Hudson has had some stellar moments since debuting in 2018, but he’s likely headed for a fresh start elsewhere. The same goes for Woodford. The Cards could save money by non-tendering Knizner, but coveted catcher Ivan Herrera still has Minor League options remaining and the well-prepared Knizner has been a serviceable backup catcher.

What’s the payroll situation?
That’s the multimillion-dollar question in St. Louis, where fans are waiting to see how the club upgrades its starting and relief pitching.

The Cardinals have $104 million already on the books for Paul Goldschmidt, Nolan Arenado, Willson Contreras, Miles Mikolas, Steven Matz and Giovanny Gallegos. When adding in the estimated arbitration raises, pre-arbitration salaries and retained/deferred money, the Cardinals payroll jumps to around $144 million, per Spotrac’s projections. That would be before any offseason additions.

What free agents could the Cardinals target?
A Cardinals franchise thought to be thin on pitching going into 2023 recorded the franchise’s first last-place division finish in 33 years. That happened largely because they finished with baseball’s 24th-ranked overall ERA (4.79), 26th-ranked starters ERA (5.07) and 23rd-ranked relievers ERA (4.47). It’s no surprise then that president of baseball operations John Mozeliak has declared that his team will be targeting “pitching, pitching, pitching.”

Shohei Ohtani will be of no help to the Cardinals as a pitcher in 2024, so they can scratch him off their wish list (I’m kidding!). Other elite arms, such as Blake Snell, Aaron Nola, Sonny Gray and Montgomery, will come with high price tags and widespread interest. Japanese pitchers Yoshinobu Yamamoto and Shōta Imanaga are also possibilities, but they will be costly as well when including posting fees.

Former Mizzou standout Kyle Gibson, who compiled a 2.6 WAR in 2023 with the Orioles at age 36, could be more of a more affordable option, as would be Michael Lorenzen and Kenta Maeda. Flaherty and Hicks could consider returning on short-term deals.

If not through free agency, who could be some trade targets?
Tyler Glasnow is thought to be a candidate for the Rays to dangle because of his $25 million salary. He will be a free agent after the 2024 season. Two-time All-Star Shane Bieber might be available if the Guardians balk at the size of his arbitration raise. Logan Webb and Logan Gilbert could be had for bats, but the costs will be high.

Jordan Walker is almost certainly untouchable, but would the Cards give up the 50-home-run potential of Nolan Gorman? Would they sacrifice the do-everything defensive skills of Tommy Edman or Donovan? What trade value do O’Neill or Carlson have following their injury-plagued seasons? Would they even listen to blockbuster deals involving Goldschmidt or Arenado?

Answers to those questions, and plenty of others, will come throughout a critical offseason for the Cards.