As much as the Chicago White Sox figure to be active in free agency this winter, I also expect GM Chris Getz to aggressively pursue opportunities on the trade market.

Chicago needs to add talent to its roster. But if history is any indication, the White Sox won’t be spending at the top of the free-agent market. That’s especially true when it comes to starting pitching.

White Sox owner Jerry Reinsdorf is notoriously risk-averse when it comes to paying pitchers. Chicago has consistently avoided long-term contracts and significant financial commitments to starting pitching, with the largest contract in franchise history for a pitcher still belonging to left-hander John Danks, who signed a five-year, $65 million extension following the 2011 season.

Danks followed that payday by posting a 25-48 record with a 4.92 ERA over 97 starts from 2012-2016.

The only significant free agent pitching addition the White Sox made during their last contention window was Dallas Keuchel, who signed a three-year, $55.5 million contract. That deal also went south, with Keuchel posting a 4.79 ERA in a White Sox uniform.

Chicago did, however, find success on the trade market, most notably when the organization acquired Lance Lynn ahead of the 2021 season.

So while there may be some intriguing free-agent starting pitchers available who fit the White Sox needs and competitive window, trading for a controllable arm might ultimately be how Chicago addresses its starting rotation.

And if that’s the case, so be it. But there are a few ground rules I think the White Sox should stick to.

Trade Prospects Over MLB Talent

Any trade, whether it’s for a starting pitcher, reliever, or outfielder, three of the needs we know GM Chris Getz wants to address, should involve the White Sox dealing from their prospect pool rather than sacrificing proven MLB talent.

That doesn’t mean Chicago should look to trade Caleb Bonemer. I think Bonemer is playing his way into the untouchable tier, and when you combine his upside with his proximity to the major leagues, he should be viewed as a player who can help the White Sox improve in 2027 rather than a trade chip.

The same goes for Roch Cholowsky. But if you look a little deeper into Chicago’s farm system, there’s plenty of talent the organization could afford to part with in exchange for controllable players who better fit its immediate needs.

Most importantly, that approach allows the White Sox to improve their roster without sacrificing their existing MLB depth.

Do the White Sox have too many infielders? Maybe. Do they know exactly what they’re going to do with a player like Sam Antonacci? Maybe not. Can Braden Montgomery reliably be penciled in as the starting right fielder on Opening Day based on what we saw in 2026? Not in my eyes.

But that doesn’t mean the White Sox should explore trading any of these players. Chicago is at a stage where the organization is building toward perennial contention, and after getting breakout seasons from so many young players in 2026, there’s still plenty to figure out.

Some of those breakout performances may prove to be more sustainable than others. The 2027 season should be about building toward contention while allowing the team’s core to rise to the top naturally, rather than anointing that core prematurely.

Is Colson Montgomery the future at shortstop for the White Sox? He very well could be, but there’s no doubt he needs to improve upon what we saw in the second half of 2026. If he’s going to continue hitting below the Mendoza line (.200) while striking out more than any other player in baseball, the White Sox may eventually need to reconsider what’s best for the organization at the position.

Can Tristan Peters repeat the success he had in 2026 that earned him a spot on the American League All-Star team? That remains to be seen. But the White Sox should have options in center field regardless.

That doesn’t just mean adding talent through free agency. It also means holding on to as much organizational depth as possible.

So should the White Sox explore trading for starting pitching? Absolutely. But I’d much rather see Chicago move a prospect like Billy Carlson or Jaden Fauske before sacrificing an MLB talent like Sam Antonacci or Braden Montgomery simply because the organization believes it has nowhere to play him.

There’s plenty of young pitching depth within the organization to deal from. 

That’s how you end up making a trade you live to regret. And with so much still undecided about the future of the White Sox, holding on to young players who have already proven they can produce at the MLB level should be a priority.