How the White Sox Can Steal Another Crosstown Classic From the Cubs
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The Chicago White Sox have been shocking the world in 2026 after a 121-loss season just two years prior. At 65-58, the White Sox are firmly in the lead for the AL Central, 5.5 games ahead of the second-place Detroit Tigers.
Now, the White Sox have a tough series ahead of them, traveling across town to Wrigley Field to face the Cubs. The Cubs, despite being 72-53, are 5.0 games back in the NL Central behind the Milwaukee Brewers. This will be a tough test for the White Sox. While they beat the Cubs in their series at Rate Field back in May, both teams are vastly different.
The White Sox have been surging since May, and the Cubs have been one of the streakier teams in baseball, having a few long winning and losing stretches. Both teams bought at the trade deadline, and some of those acquisitions will pitch in this upcoming series.
Here's how the White Sox can steal another series from the Cubs!
Figure Out the Pitching Situation
The lack of a true fifth starter and Davis Martin's injury have left the White Sox with two open rotation spots. As of now, the White Sox have Luis Castillo starting on Monday, but have Tuesday and Wednesday listed as TBA.
If no moves are made, Erick Fedde and José Urquidy will likely make those two starts, which puts added stress on the bullpen. Fedde and Urquidy have struggled, and it would be less than ideal to have them both make starts during a crucial series.
Drew Thorpe could be added to the major league roster during this series to make his first start since 2024. Johnathan Cannon or Shane Smith could also be elevated during this series. Either way, the White Sox need to figure it out fast, or they could be in for a long series.
Hit The Starters Hard
This one is self-explanatory, but still important. Shota Imanaga, who will be starting on Monday, has been terrible in two starts against the White Sox. In July of 2025, he gave up seven runs in just three innings against the White Sox. Chase Meidroth and Colson Montgomery both had home runs off Imanaga.
Kevin Gausman will start on Tuesday, but he had a horrible last start with the Cubs after being acquired at the deadline. Gausman gave up six runs in 4.2 innings against the Washington Nationals.
Finally, Clay Holmes will start on Wednesday and has been good since returning from injury. In two starts with the Cubs, Holmes has a 3.38 ERA. Still, Holmes is the kind of pitcher who will give the White Sox plenty of balls to hit, and it will be their job to capitalize.
Colson Montgomery Needs to Get Out of Slump
While Colson Montgomery is showing signs of breaking out of a prolonged slump, he'll be one of the offensive keys to this series. When he's hitting well, this offense is unstoppable. Montgomery, in his last seven games, is slashing .179/.233/.321. And that's just not going to cut it.
In recent days, we've seen Braden Montgomery, Miguel Vargas, and Tristan Peters break out of slumps. Could the talented shortstop join them? The White Sox really need it!
It's not hyperbole to say that this series could make or break both teams' seasons. Buckle up because this will be a series to remember!
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Matthew Singer is a contributor for White Sox on SI. Before joining SI in 2026, he worked for Heavy as an MLB contributor and Cubs on SI. Singer has a master's degree in sports journalism from the Walter Cronkite School of Journalism and Mass Communication at Arizona State University. He loves sports more than anything in the world.