White Sox Head to Cleveland With Season on the Line

It's been an ugly stretch of baseball for the Chicago White Sox as the regular season winds down. Chicago is 4-10 over its last 14 games, falling from 72-63 to 76-73 with only a few weeks remaining.

At this point, the White Sox are desperately trying to remain above .500, a position they have maintained since May 26, when they were 27-27.

Yet as bad as things have been, there's still an opportunity for the White Sox to win the AL Central, secure the No. 2 seed in the American League and make some noise in the playoffs. Doing so will require the team to get hot, and that turnaround needs to begin immediately.

The White Sox have occupied first place in the AL Central since July 4. But with their lead down to just half a game, they will head to Cleveland this week with their entire season on the line.

It'a by no means a stretch to say that the White Sox are playing for their season this week. Shortstop Colson Montgomery acknowledged as much following Sunday’s game.

This team is well aware that everything could come down to what happens over the next three days.

“This is meaningful baseball. These are playoff games. This is determining-your-season type of stuff. If you come out flat, your season could be over. We’re going to be juiced up for it,” Montgomery said.

Hopefully, that juice will be enough to awaken an offense that has scored three runs or fewer in five of its last six games.

That is, perhaps, the most concerning aspect of the White Sox’s recent play. There has not been one singular problem to correct. There have been games in which the starting pitching imploded and Chicago never had a chance to win. There have been others in which the offense went completely quiet.

Then there are games like Sunday afternoon, when poor defense and a costly error by Montgomery came back to bite the White Sox. The team has not received enough length from the front end of its pitching staff, and the offense has consistently struggled to deliver with runners in scoring position. That makes it difficult to trust Chicago in these high-pressure situations.

But over the next three days against the Guardians, everything could flip on its head.

Chicago needs to win at least one game in the series to secure the season tiebreaker over Cleveland. That's a necessity for obvious reasons.

The tiebreaker could prove crucial during the final weeks of the season. Beyond that, a sweep would leave the White Sox 2.5 games behind Cleveland in the division, which might as well be the death knell at this stage.

If the White Sox win one game but lose the series, they would leave Cleveland in second place by half a game, although they would carry the tiebreaker into the home stretch. A series victory would allow Chicago to remain in first place and create some additional breathing room.

Given the negative spiral the White Sox have been caught in recently, I am comfortable taking the leap and calling a series win against the Guardians a necessity. Lose the series, and Chicago probably loses the division while blowing a golden opportunity presented by the dynamics of the 2026 American League.

It all starts Monday night, with Sean Newcomb taking the ball as the White Sox opener in Cleveland. The Guardians are putting their best foot forward, lining up Gavin Williams for Monday night before turning to Foster Griffin and Parker Messick in the final two games of the series.