For the players inside the Chicago White Sox clubhouse, losing Game 5 of the ALDS was a tough pill to swallow for multiple reasons.

There’s the obvious disappointment of failing to capitalize on three consecutive opportunities to close out the series and advance to the ALCS. Opportunities like that don’t come around very often, especially in White Sox history.

But there’s also a rather somber feeling among White Sox players as they come to terms with the reality of professional sports and the inevitable roster turnover that comes with every offseason.

Chicago may have its young core of players returning in 2027, but there will still be changes to a team that bonded in a special way over the last seven months.

Never again will it be this exact group of 26 guys. Newcomers will join the team, old friends will find homes elsewhere, and a different group with its own chemistry will attempt to build on this season’s success.

That realization seemed to weigh heavily on White Sox players over the weekend. And now, with a potential MLB lockout looming, the organization enters an offseason filled with uncertainty and months of waiting to see what the 2027 roster will look like.

Consider this your guide to the White Sox roster and which players may not be returning to the South Side in 2027.

Given the youth on this roster, the White Sox don’t have many players bound for free agency. But of the 26 players on Chicago’s postseason roster, five will become unrestricted free agents this winter.

35-year-old outfielder Randal Grichuk is back on the open market after one of the most memorable single-season performances by a White Sox veteran in recent memory.

Grichuk started the 2026 season with the New York Yankees before being released and subsequently picked up by the White Sox. He proceeded to hit 15 home runs with a .926 OPS over 101 games in a White Sox uniform, becoming an important piece of Chicago’s surprising postseason run.

There’s an outside chance Chicago brings him back, but I think Grichuk ultimately lands elsewhere in free agency.

Outfielder Tommy Pham made a handful of appearances for the White Sox toward the end of the regular season, then managed to work his way onto the postseason roster. He’s now a free agent, however, and I don’t expect him to return in 2027.

Catcher Jake Rogers was acquired by the White Sox out of necessity after the backup catching situation became a disaster and Joey Bart suffered an injury shortly after the trade deadline.

Bart should be healthy heading into 2027, and I expect the White Sox to make a conscious effort to add more catching depth throughout the organization. That likely leaves Rogers exploring other opportunities in free agency.

Left-handed pitcher Sean Newcomb might have been the unsung MVP of the White Sox pitching staff this season.

Newcomb logged 90.1 innings during the regular season with a 3.09 ERA, bouncing between roles as an opener, long reliever and high-leverage bullpen option. His versatility made Will Venable’s life considerably easier and helped Chicago navigate a pitching staff that rarely operated with a traditional starting rotation.

As much as the White Sox would probably like to have Newcomb back, there should be lucrative offers available to him in free agency. He could also have opportunities elsewhere to compete for a starting rotation spot, something he’s expressed plenty of interest in pursuing.

I’d be surprised if Newcomb returned to the South Side next year.

The same goes for Erick Fedde, although that’s not because he can’t still be productive or because the White Sox don’t appreciate what he brought to the team in 2026.

Fedde finished the season with a 3.83 ERA over 141 innings pitched, and it’s hard to imagine the White Sox making the postseason without him helping steady the pitching staff throughout the year.

Chicago simply has too many mouths to feed between its surplus of young pitching talent throughout the organization and the clear upgrades the front office should look to make to the starting rotation this offseason.

With those factors in mind, it would be surprising if the White Sox felt compelled to bring Fedde back for his age-34 season.

Don’t be surprised if Andrew Benintendi is playing elsewhere in 2027.

While he served his role well in a platoon, drove in 78 runs for the White Sox and came through in plenty of clutch situations, Benintendi didn’t bring much to the table during the postseason. His lack of defensive value also makes it increasingly difficult for the White Sox to justify his place on the roster moving forward.

There’s only one year remaining on the five-year, $75 million contract he signed with Chicago before the 2023 season, which will pay him $15.1 million in 2027.

I expect the White Sox to make an effort to get younger and more athletic this offseason, potentially adding an established everyday bat to the outfield mix. Such an addition could leave Benintendi without a clear role on the roster and make him an obvious trade candidate, especially if Chicago is willing to eat a portion of his remaining salary to facilitate a deal.

The other area to watch for a potential offseason trade is the surplus of young starting pitching throughout the organization.

I won’t single out any specific names as likely trade candidates, mostly because I could see this going a number of different ways. But Chicago has more starting pitching candidates than it knows what to do with, which is somewhat ironic considering the team’s starting rotation wasn’t particularly strong in 2026.

Hagen Smith, Noah Schultz, David Sandlin, Drew Thorpe, Tanner McDougal, Shane Smith and Grant Taylor are all pitchers who could be in the mix for a starting rotation spot in 2027.

And that doesn’t even include right-handers Sean Burke and Davis Martin, who will likely enter next season with spots already secured in the rotation. Nor does it account for any external additions the White Sox make, which should be a priority for the front office this winter.

Rather than stash some of that young talent in the minor leagues, why not use the surplus to address other areas of need?

It’s always valuable to have organizational depth when it comes to young, talented starting pitching. And I certainly don’t think the White Sox should completely deplete that depth in pursuit of immediate upgrades.

But as valuable as young pitching can be for the future, relying too heavily on inexperienced arms can become problematic in the middle of a pennant race.

The expectations have changed on the South Side. In 2027, the White Sox should be looking to win the AL Central, take another step forward and establish themselves as legitimate contenders in the American League once again.

That means the front office can no longer operate exclusively with an eye toward the future. There’s an opportunity to win right now, and Chicago should be willing to capitalize on it.

Rather than relying entirely on its young pitching prospects to take the next step, don’t be surprised if the White Sox use some of that talent as trade capital to acquire an established veteran or two before spring training.

If there’s one thing I’d emphasize to the White Sox front office moving forward, it’s the importance of not becoming complacent with a young team that’s starting to grow together.

As we all know, development isn’t linear. You can never count on a young, unestablished player to improve year after year, and the White Sox shouldn’t simply assume that the same group will be better in 2027 because it has another year of experience under its belt.

The time is now for the White Sox to pour gas on the fire, acquire proven veteran talent and take this team to another level.

Naturally, that will mean a roster that looks different in 2027 than the one we saw in 2026, even if the bones and foundation of the franchise remain the same.