When Can White Sox Fans Expect Action in Free Agency?

Chicago White Sox fans are expecting a busy offseason after returning to the playoffs in 2026 with an 84-78 record. Now's the time for Chicago to begin pushing its chips in and making moves in free agency.

It's time to build a World Series contender, which will be no easy task given some of the obstacles the White Sox are facing this winter.

On December 1, the collective bargaining agreement will expire, and a lockout is expected to begin. In anticipation of that lockout, we should see a very active free agent market rather than a drawn-out process. Teams and players alike are motivated to get deals done while the current league structure and roster rules are in place.

Fast and furious. That's how I've already described the free agency period to come. But it's already been a handful of days since players became eligible to sign, and there's been no significant action to speak of on the transaction wire.

White Sox fans may be wondering when they can expect things to pick up and the hot stove to get cooking. Sure, Chicago already made a few moves by claiming Graham Pauley off waivers and signing Alec Marsh to minor league contract. But what about the real, big splash, MLB deals? For that answer, we need to look back at the last lockout Major League Baseball faced.

There was a similar situation following the 2021 season. While anticipating a lockout, there was an unusual surge of players signing before the start of December to secure their deals in time.

Javier Báez, Corey Seager, Robbie Ray, Max Scherzer, Marcus Semien, and Kevin Gausman all signed contracts worth north of $100 million before the lockout. However, it wasn't until the last possible moment that the market really got going.

That winter, free agency opened on November 8. There was one early signing, with Andrew Heaney agreeing to a one-year, $8.5 million contract with the Los Angeles Dodgers on November 9.

The real action didn't start until the Detroit Tigers brought in left-handed pitcher Eduardo Rodríguez on November 15 with a $77 million contract, a full week after free agency had officially opened.

From there, you started to see some dominoes fall. Manny Piña to the Braves, Noah Syndergaard to the Angels, and Justin Verlander returning to Houston. Relief pitchers like Aaron Loup and Kendall Graveman also found homes, while Anthony DeSclafani re-signed with the Giants.

The real wave of chaos started on November 26, when the New York Mets made three signings in one day. New York brought in Starling Marte, Mark Canha, and Eduardo Escobar, which lit the fuse across the league. Gausman went to Toronto, the Texas Rangers signed both Marcus Semien and Corey Seager to mega contracts while also landing right-handed pitcher Jon Gray, the Mets answered with a big deal for Max Scherzer, and Robbie Ray got paid by the Seattle Mariners.

All of it went down within a handful of days of the lockout. It was a late frenzy, with teams working through the week of Thanksgiving to get as many deals done as possible.

What does all this mean for the White Sox this year? Come Monday, it will officially be one week since free agency opened. That's around the time in 2021 when we started to see the first few pieces come off the board.

For each of the next two weeks or so, I'd expect a handful of newsworthy transactions to go down. A few players will jump the market and sign early. There will be a few trades. But when you look at the top players on the free agent market, pitchers like Tarik Skubal, Freddy Peralta, and Michael King, and outfielders like Seiya Suzuki and Randy Arozarena, they're all likely to land contracts worth more than $100 million.

Just like we saw in 2021, I expect those deals to be negotiated in the final days leading up to the lockout. That final week of November around Thanksgiving is when it will all take place. 

So while White Sox fans may be getting anxious for some moves, especially with the forecasted early action, history tells us that the true bedlam is still a few weeks away. That being said, free agent signings of substance should start happening in just a few days.