- August 18, 2026
- Updated 2:45 am
Anticipation Builds for Possible Cubs-Sox World Series
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- August 18, 2026
- Professional Sports Sports
Back in the summer of 2008, Chicago baseball fans held onto dreams of a crosstown World Series. That year marked the last time the Cubs and White Sox squared off with serious playoff hopes in the regular season. While the dream didn’t materialize then, it might now. ESPN puts the odds of a Cubs-Sox World Series at 63-1.
“Sign me up,” said Cubs manager Craig Counsell. He seems excited about the possibility. Will Venable, Sox manager, presumably shares that enthusiasm.
As a journalist who has covered the City Series since 1997, I’ve witnessed countless matchups between these teams. My first was at Comiskey Park in August 1981, where exhibition games welcomed the teams back after a strike.
From 2006 to 2010, the Cubs-Sox rivalry was intense. There were dramatic moments like Michael Barrett’s punch on A.J. Pierzynski and memorable quips from managers like Lou Piniella and Ozzie Guillen. Although neither team reached the World Series in those years, the atmosphere was electric.
This year might ignite a new era of the City Series. The Cubs currently aim for the top wild-card spot, likely facing the Philadelphia Phillies. Meanwhile, the Sox are aiming for a victory in the American League Central and hold hopes for a first-round playoff bye.
White Sox manager Venable focuses on the immediate challenge. “We are trying to win today,” he emphasizes. His priority is tonight’s game against Shota Imanaga and the Cubs.
The significance of clinching the No. 2 seed for the Sox means possibly avoiding AL East teams until the AL Championship Series. They could gain momentum while Tampa Bay, New York, and Boston contend amongst themselves.
The Cubs face questions about their pitching lineup with fluctuations involving Edward Cabrera, Javier Assad, and others. For the Sox, uncertainty looms over pitching starters, as noted by Venable’s cautious approach.
The historical rivalry between the Cubs and Sox offers the potential for a competitive series. The Cubs hold a narrow lead in all-time regular-season games, but the White Sox’s win in the 1906 World Series remains a high point.
Manager Counsell acknowledges the historical significance. “Someone pointed out this is the biggest series since 1906,” he says, giving a nod to Chicago’s baseball history.
The anticipation for a thrilling series is palpable. Both teams have significant work ahead, but fans and players alike can feel the excitement building.