2026 Cubs, White Sox join short list in Chicago baseball history — their postseason stays might be short, too

Think about all the pieces that had to fall into place for the Cubs and White Sox to clinch playoff berths within two minutes of each other Thursday. That includes the Cubs overcoming all sorts of pitching challenges and the Sox overcoming years of ineptitude.

Yet there they were, celebrating simultaneously, the Cubs at home and the Sox in Kansas City. It was a surreal visual, marking only the fourth time in history that the teams made the playoffs in the same season.

Think about that, too. In more than 125 years of coexistence, the Cubs and Sox have played in the same postseason only three times.

“When I first heard that, it was pretty amazing,” Sox general manager Chris Getz said Friday.

Getz and Cubs baseball president Jed Hoyer are good friends, and they exchanged text messages during the historic day.

“I guess maybe he was a better friend; he texted me first,” Getz said. “I didn’t even know what was going on in their situation.”

Of the four times, this was the unlikeliest, considering the Sox lost more than 100 games in 2023-25. The last time was in 2020, the pandemic-shortened season, when the teams clinched five days apart. In 2008, they clinched 10 days apart, with the Sox needing two extra days because of a rainout and a one-game playoff for the division title.

The first time was in 1906, when the teams won their respective pennants 14 days apart. No silly wild-card round back then. Do not pass “Go,” and head straight to the World Series. Though the Cubs (116-36-3) won 23 more games than the Sox (93-58), the Sox won the series 4-2. The thing is, none of us saw it, so it’s hard to appreciate it.

But just imagine it.

“If they were to play each other in the World Series,” Steve Stone said, “it would be one of the great things to ever happen to the city of Chicago.”

Stone knows a thing or two about Chicago baseball. Outside of three years pitching for the Orioles (1979-81), he has been a Cubs or Sox player or a Cubs or Sox broadcaster almost every year since 1973.

“I’ve very much fallen in love with this city,” Stone said. “I love to see both sides of town celebrating.”

But one has more reason to celebrate.

“The Cubs were supposed to be there; the White Sox were not,” Stone said.

Indeed, but the Sox appear to have the easier path to success in the postseason.

The Sox have a better bullpen and less-intimidating competition, whether they end up winning the division or landing in the wild-card round. A division title gives them the No. 2 seed and a spot in the American League Division Series, where they could face the Astros, Guardians or Rangers, teams on their level.

The Cubs might have the best offense and defense in baseball, but bad pitching can sabotage both. Like Harry Caray used to say, “What about the pitching?” Then there’s the Cubs’ competition in the National League with superpowers such as the Braves, Brewers and Dodgers. But before facing any of them, the Cubs must survive the wild-card round.

Still, crazy things happen in the postseason. Teams get on a roll, and there’s no stopping them. Sox fans remember the 2005 team, which went 11-1 in the postseason and won the World Series. Cubs fans recall the 2016 team, which rallied in every round of the playoffs and won the World Series.

Imagine them meeting in the Series 120 years later.

“We’ve had some clubhouse staff born and raised in Chicago,” said Sox pitcher Davis Martin, the team’s longest-tenured player. “I always asked, what would a White Sox-Cubs World Series do? [They’d say,] I don’t know if the city of Chicago could handle it.”

“I think traffic would be out of control,” Getz said.

Probably, but what’s really out of control is the city’s fondness for teams that won little or nothing. The 2016 Cubs and 2005 Sox could use some company.

Cubs fans of a certain age grew up hearing how incredible the summer of 1969 was, only to learn that the team fell apart in September and lost the division to those dastardly Mets. The 1983 Sox might be even more celebrated than the 2005 champs, and they lost to the Orioles in the AL Championship Series.

But it’s unlikely that either team will get to the World Series. Still, it should be fun finding out — perhaps more for one team than the other.

“If both teams get knocked out in the first round,” Stone said, “it will be a major disappointment for the Cubs, and it will be something that Sox fans will appreciate having gotten there.”

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