As we reflect on the 2026 season for the Chicago White Sox, celebrate the team’s accomplishments and mourn their recent playoff defeat, it’s also time to start looking ahead to the future.

What will 2027 look like for Major League Baseball? And more importantly, what will it look like for the White Sox?

Of course, in the wake of a postseason defeat, there are plenty of pressing questions that need to be answered. Perhaps none is more significant for the White Sox than finding a solution for their starting rotation.

Plenty went wrong for Chicago to blow a 2-0 lead in the ALDS against the Cleveland Guardians. But of all the issues this team faced, the starting rotation was a clear weakness throughout the regular season. Those concerns ultimately carried over into October, when the White Sox were forced to rely on bullpen games for the majority of their postseason run.

Sean Burke was the only traditional starting pitcher the White Sox had on their postseason staff. That’s not a recipe for a World Series run.

And as the page turns to 2027, competing is the new standard for the White Sox. The expectation should be that Chicago fields a team capable of winning the division and making an even deeper postseason run.

That starts with answering one of the biggest questions facing this franchise: How are the White Sox going to fix their starting rotation?

Here’s the issue the White Sox run into. They have depth. All kinds of young, talented pitching depth throughout the organization. But it’s not necessarily the kind of depth you can rely on when you’re a team with aspirations of contending.

Sean Burke and Davis Martin are likely locked into rotation spots for 2027. Anthony Kay was serviceable in 2026 and remains under contract for $5 million next season. Whether he’s in the rotation or used as a long relief arm is a different conversation, but Kay will be on the team and in the mix during spring training.

Beyond that, the White Sox have young pitchers like Noah Schultz, David Sandlin and Hagen Smith, all of whom made their MLB debuts in 2026, showed flashes of their potential and project as starting pitchers in the long term.

Then there’s Grant Taylor, Chicago’s multi-inning closer, who has publicly expressed his desire to become a starting pitcher in the past. It’s possible the White Sox explore that option once again now that Taylor has a full season in the big leagues under his belt. Do they try stretching him out during spring training to maximize his value?

Drew Thorpe is another one of the organization’s most promising young arms. After pitching well during the second half of the season in the minor leagues, Thorpe can now be considered fully recovered from Tommy John surgery. He’ll be in the mix for a rotation spot, as will pitching prospect Tanner McDougal.

Let’s not forget that the White Sox also have Shane Smith, an All-Star in 2025 who was the team’s Opening Day starter in 2026. They also have Luis Castillo under contract and will need to figure out what his role looks like moving forward.

All of these arms. All of these options. And yet, I don’t think you can put together a starting rotation for 2027 that you can confidently trust using only the names I just listed.

That’s not the upgrade the White Sox need. That’s banking on young talent, crossing your fingers and hoping for the best. It’s a perfectly reasonable approach for a rebuilding team, but not for one with legitimate aspirations of contending.

The White Sox need to add proven starting pitching talent to this roster. They can’t simply count on internal development to solve their biggest weakness.

The question is, how?

The free agent class features pitchers such as Tarik Skubal, Sonny Gray, Michael King, Foster Griffin and Freddy Peralta, among others. There’s plenty of talent to choose from if Chicago is willing to spend at the top of the market.

I think it’s realistic for the White Sox to sign one free agent starting pitcher who can make a significant impact. But if the team is looking to make multiple additions, I’d strongly consider exploring the trade market.

So many of the young pitchers I mentioned within the White Sox organization have legitimate value. They may not be the perfect fit for this starting rotation right now, given the trajectory of the club and their lack of MLB experience, but that doesn’t mean they can’t be valuable pieces elsewhere.

And I certainly don’t think the White Sox should completely deplete their organizational pitching depth. That would defeat the purpose of building such a strong collection of young arms in the first place.

But if moving one, two or even three talented young pitchers allows Chicago to acquire a premier starting pitcher with multiple years of club control, it might be in the team’s best interest.

Let’s say the White Sox sign Michael King in free agency. Then, they turn around and trade for a pitcher like Reid Detmers from the Los Angeles Angels.

Suddenly, Chicago could enter the 2027 regular season with a rotation featuring King, Burke, Detmers and Martin, with an abundance of talented young arms competing for the fifth spot and providing depth behind them.

That’s a recipe for success. It’s a rotation with proven MLB talent, legitimate upside and enough organizational depth to withstand injuries or underperformance over the course of a 162-game season.

And most importantly, it wouldn’t require the White Sox to mortgage their entire future. They could maintain a strong foundation of young pitching talent while adding the established arms necessary to take another step forward.

The White Sox spent the last several years stockpiling young talent and building toward a competitive window. After everything they accomplished in 2026, that window is officially open.

Now it’s time to start acting like it.

The White Sox don’t need to abandon their commitment to developing young pitchers. But they can’t afford to enter another season hoping that enough of those pitchers take the next step at the same time.

They need proven talent. They need reliability. And they need a starting rotation capable of carrying them through October.

All it would take is for the White Sox to be a little aggressive.