With the World Series about to begin, the MLB offseason will be here before you know it — and it’ll finally be time for the stove to get hot.

For good reason, Chicago White Sox fans have plenty of anticipation heading into this winter. There are real questions about how aggressive the organization will be in improving a roster that showed flashes of life during the second half of 2025.

South Side faithful are growing impatient. The White Sox have lost 100 games in three consecutive seasons, and it’s time for Chris Getz to start surrounding his promising young core with legitimate, veteran talent.

Consider this your guide to all things offseason — every key date and deadline that could shape the future of White Sox baseball.

Exclusive Free Agents and Trades — After the World Series

Immediately after the conclusion of the World Series, teams are allowed to negotiate exclusively with their own free agents for a five-day window.

At this time, MLB also lifts its “transaction freeze.” Teams can discuss and negotiate trades behind the scenes during the Fall Classic, but no deals can be officially filed with the league until a champion is crowned.

Free Agency Opens — Five Days After the World Series

Five days after the World Series ends, free agency officially opens at 5 p.m. ET. The exclusive negotiating window closes, and players are free to sign with any club.

By this date, teams must also make decisions on qualifying offers and contract options — player, club, and mutual. Declining an option immediately makes a player a free agent.

The White Sox have notable decisions to make on Luis Robert Jr. and Martín Pérez. Robert’s $20 million club option is expected to be exercised, while Pérez’s $10 million mutual option could go either way.

Eligible free agents can be extended a qualifying offer of $22.025 million for the 2026 season, but no current White Sox players are expected to receive one.

Additionally, players on the 60-day IL must be reinstated to the 40-man roster. For the Sox, that includes Drew Thorpe, Ky Bush, Miguel Castro, and Prelander Berroa — meaning a few tough roster cuts could follow, even with the current 40-man sitting at 35.

GM Meetings — November 10–13, 2025

The next major checkpoint comes when executives from all 30 teams gather for the GM Meetings in San Antonio, TX.

This is where groundwork gets laid for trades and free-agent signings — a lot of deals that “come together quickly” later in the winter usually start here.

Protection Deadline — November 18, 2025

Teams must add eligible prospects to their 40-man roster by November 18 to protect them from the Rule 5 Draft.

The White Sox have several pitchers at risk of being exposed if they’re not added. As we saw with Shane Smith’s rookie year, losing the wrong player can be costly.

The same date also marks the start of the Owners Meetings (Nov. 18–20 in New York).

Tender / Non-Tender Deadline — November 21, 2025

All arbitration-eligible players must be offered (“tendered”) a 2026 contract by this date — otherwise, they become free agents.

Winter Meetings — December 7–10, 2025 (Orlando)

The Winter Meetings are the most electric week of the offseason. Agents, executives, and reporters all gather under one roof, and this is where the hot stove truly starts to boil.

MLB Draft Lottery — December 9, 2025

Live from the Winter Meetings, MLB will conduct its annual draft lottery.

The White Sox own the best odds to land the No. 1 overall pick — a drawing that could define the next decade of baseball on the South Side. If there’s a generational talent at the top of the 2026 class, this lottery could decide whether he ends up in Chicago.

Rule 5 Draft — December 10, 2025

The Rule 5 Draft takes place the very next day. The White Sox will hold the second overall pick and could once again find value — just as they did last year when they selected Shane Smith first overall.

For context, Marlins catcher Liam Hicks went second in that same draft.

International Signing Period — December 15, 2025

The international amateur signing period for the 2025 class officially closes.

Arbitration Filing Deadline — January 8, 2026

If arbitration-eligible players and teams haven’t agreed to contracts by now, both sides submit proposed salary figures. Arbitration hearings are then scheduled — something most clubs prefer to avoid altogether.

Expect Mike Tauchman, Steven Wilson, and Derek Hill to be part of these discussions if they’re tendered contracts.

International Amateur Signing Period Opens — January 15, 2026

A new international signing period begins, running from Jan. 15 to Dec. 15, 2026.

Pitchers and Catchers Report — February 12, 2026

Circle the date: February 12th marks the voluntary report date for pitchers and catchers. From there, spring training officially kicks off, and by late February, exhibition games will be underway.

Baseball will be back — and by then, we’ll know exactly how the White Sox chose to shape their next chapter.