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2023-24 MLB/White Sox/South Side Sox offseason calendar

Our annual guide to everything happening on site and in White Sox baseball, from now till Opening Day

While baseball’s offseason deprives us of games, it doesn’t mean there’s not a lot of action over the winter.

The conclusion of the World Series on November 1 ended the baseball season, and the annual stampede of players to free agency is underway. Add to that, there’s a lot of other business to take care of here at South Side Sox.

Here’s your clip n’ save look at everything happening that’s worth happening, between World Series end and Opening Day 2024.

(Bookmark this page, and/or stop in frequently, as at least early on we are likely to be tweaking and adding items!)

October 31

Our first vote in the SSS Top Prospect Poll, from 1-50, with your votes on the Top 50 helping us fill out our White Sox Top 100 Prospects.

November 2

All players with at least six years of service time who are not under contract for 2024 automatically become free agents. Also, minor league players with six years of service will also become free agents (unless added to the 40-man roster). Here are all of the 2024 free agents.

November 2-6

The first five days after the World Series is a “quiet period”: Clubs can talk to free agents, but can’t sign them.

November 3

Mr. 100, Jason Matthews, kicks off our Top 100 Prospect countdown. We’ll aim to have No. 1 announced well before Opening Day.

November 5

Gold Glove winners will be announced live on ESPN at 6:30 p.m. CT. Luis Robert Jr. is a finalist in center field.

November 6

At 4 p.m. CT the “quiet period” ends, and clubs must decide whether or not to extend one-year qualifying offers to their free agents. The qualifying offer is anticipated to be $20.5 million, almost a million more than the $19.65 million last year. The White Sox won’t be issuing any qualifying offers this year. (Do they ever?)

But as it might pertain to players on other clubs you think the White Sox might pursue (cough Cody cough Bellinger cough), players who receive a QO have 10 days (until November 14) to decide whether or not to accept. If they don’t, they are free agents, immediately eligible to sign with another team — and if so, their former team will get draft compensation for the signing.

The end of the “quiet period” is also the deadline to settle 2024 contract options. We already know how those will play out, as [redacted] pockets $4 million to become a free agent by declining his mutual option, and the White Sox cut Tim Anderson for $1 million and cut Liam Hendriks for $1.5 million per year over the next decade.

Here is everyone with such contract options for 2024.

Teams also must move all players on the 60-day injured list back to the active roster, as the 60-day only applies to the active season. That means Romy González, Matt Foster and Jimmy Lambert all count as roster spots from here on (Foster might go non-tendered, freeing up a 40-man spot).

Finally, this Monday marks the announcement of finalists for the BBWAA MLB awards, live on MLB Network at 5 p.m. CT.

November 7-9

General managers meetings in Scottsdale, Ariz.

November 9

Louisville Silver Slugger Awards will be announced for each position, live on the MLB Network at 5 p.m. CT.

November 13

The Jackie Robinson Rookie of the Year Award winners will be announced, live on the MLB Network at 5 p.m. CT.

November 14

Manager of the Year awards will be announced, live on the MLB Network at 5 p.m. CT. Pedro Grifol is not expected to be in the running for AL honors.

November 14-16

The Owners’ Meetings take place in Arlington, Texas. These are almost always snoozefests custom-made for GM pablum (see Hahn, Rick). However, this year a team has decided to leave its home of some 55 years, so it’s at these meetings owners will take a vote on the A’s relocating to Las Vegas. Support from 22 of the other 29 owners is needed to approve the move.

By 3 p.m. CT on November 14, players who have received qualifying offers must accept or reject them. Players accepting the offer return to their previous team, while players who reject the QO become free agents, with draft pick compensation attached to their signing. Last year, 14 players received the $19.65 million QO, but just two accepted it: Rangers LHP Martin Perez and Giants outfielder Joc Pederson.

By 5 p.m. CT on November 14, teams must add eligible minor-leaguers to their 40-man rosters, or risk losing them in the Rule 5 draft. College players drafted no later than 2020, high school players drafted no later than 2019 and international players signed no later than 2019 are Rule 5 draft-eligible this year.

November 15

Cy Young awards will be announced, live on the MLB Network at 5 p.m. CT.

November 16

MVP awards will be announced, live on the MLB Network at 5 p.m. CT.

November 17

After the Owners’ Meetings end, the MLB non-tender deadline (6 p.m. CT) strikes. All teams must offer their pre-arbitration and arbitration-eligible players a contract for 2024 by this deadline. Players who do not receive a contract offer are considered “non-tendered” and become free agents. The new CBA pushed this date up from early December to the Friday immediately before Thanksgiving.

White Sox awaiting a tender decision are Dylan Cease, Andrew Vaughn, Michael Kopech, Touki Toussaint, Garret Crochet, Matt Foster, Trayce Thompson, Clint Frazier. Thompson and Frazier were outrighted on November 3.

November 20

The 2024 BBWAA Hall of Fame ballot is released, with voters casting their ballots through year’s end.

November 25

This year’s SSS Veterans’ Committee Ballot will be released, with results published on December 2.

December 3

The Contemporary Baseball Era Committee of the Hall of Fame meets to discuss candidates, with the results of the vote announced live on the MLB Network at 6:30 p.m. CT. There are eight candidates, including almost-White Sox manager Cito Gaston, and Hawk Harrelson bestie/umpire Joe West.

December 3-6

The MLB Winter Meetings take place in Nashville.

December 5

The MLB Draft lottery will take place. The 18 teams that did not make the postseason all have a shot at the No. 1 pick, with the worst teams getting the highest odds. The White Sox have a 14.7% chance at the top pick. (Conversely, if the lottery goes south for the South Siders, they could drop as low as pick No. 10.)

Also, winners of the Hall of Fame’s 2023 Frick Award (for broadcasters) and BBWAA Career Excellence Award (for writers) are announced.

December 6

The Rule 5 draft ends the Winter Meetings. Players taken in the Rule 5 draft must remain on their new team’s major league roster all season, or be offered back to their original team. Nick Avila was a Rule 5 pick last year for the White Sox, and oddly, he was sent back to the San Francisco Giants before the season started; bad call there, as Avila went 14-0 with a 3.00 ERA in Triple-A in 2023.

December 7

The most fun of all our Hall of Fame elections returns for a fifth run on this day, as we release the South Side Sox White Sox Hall of Fame ballot. Bonus categories will be included, once again. Results will be posted on-site before Christmas.

December 13

The 2023 international signing period closes at 4 p.m. CT.

January 12, 2024

Teams must exchange salary arbitration figures with arbitration-eligible players by this date. Players and teams can avoid arbitration by reaching an agreement any time prior to the beginning of an arbitration hearing, which is how things play out the vast majority of the time.

January 15

This date marks the beginning of the 2024 international signing period, as of 8 a.m. CT. Because there is still no international draft, players from countries outside the U.S., Canada and Puerto Rico can sign with any team.

January 16

SSS releases its Hall of Fame ballot, with results published on site a week later.

January 19-21


Oh shit, wait, the cowards canceled it again this year.

January 23

The National Baseball Hall of Fame announces its 2024 class in a live MLB Network broadcast at 5 p.m. CT. This year’s ceremony is in Cooperstown, New York, on Sunday, July 23. First-timer Adrián Beltré, as well as Todd Helton (sixth time on the ballot) are expected to be elected. Mark Buehrle is in his fourth year on the ballot.

January 29-February 16

Arbitration hearings for any eligible players who have not reached agreement on contracts with their teams.

February 14

Reporting day for all White Sox pitchers and catchers, to Camelback Ranch in Glendale, Ariz., for spring training.

February 21

The likely reporting day for all White Sox players for spring training, although most everyone will be in the fold during the previous week.

February 23

The White Sox open their 2024 spring training schedule on the road against the Cubs, at 2:05 p.m. CT, Sloan Park.

March 20-21

For the first time, MLB will play regular season games in Korea, as part of the Seoul Series. The Dodgers and Padres will play two official games overseas, then return to the United States for their final two spring training games (Dodgers-Angels, Padres-Mariners).

March 28

Projected Opening Day starter Dylan Cease and the White Sox will open the 2024 season Thursday, March 28 against the Tigers at Sox Park at 1:10 p.m. CT. Pack your parkas.

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