Chicago is headed into October with a rare kind of baseball buzz: both the Cubs and White Sox are in the postseason in the same year, something that has happened only four times ever.
The Major League Baseball Postseason starts Tuesday, and both teams punched their tickets Friday, within two minutes of each other. As things stand, each club is lined up for the Wild Card round. The White Sox, though, still have a shot at the American League Central title and a first-round bye.
For Chicago, this kind of overlap has been almost unheard of. The last time both teams reached the playoffs was in the pandemic-shortened 2020 season.
Before that, it was 2008. The first time came all the way back in the 1906 World Series, when the White Sox beat the Cubs 4 games to 2.
This year’s White Sox run already stands alone in another way. They became the first team in MLB history to make the postseason after back-to-back 100-loss seasons.
Around the city, the story of the two teams has felt very different, even as the destination ended up the same.
Al Yellon, managing editor of the sports blog Bleed Cubbie Blue, called it, "This has been maybe weirdest Cubs season I've ever experienced."
"You know, two 10-game winning streaks, a 10-game losing streak, basically everybody on the pitching staff getting injured," he said.
On the South Side, Richard Lindberg, an author and historian who has written four books on the White Sox, said Sox fans have learned to brace for the worst.
battle-hardened Sox fans "always expect the worst to come before the best."
"So, I guess you can say this has been a renaissance year for the White Sox," he said.
There’s still more baseball to play before the bracket is set, and the possibility of a Cubs-White Sox World Series would send the city into another level of frenzy.
"I mean, this city would go crazy, absolutely crazy," Yellon said.
Lindberg wasn’t buying the odds of that rematch happening anytime soon.
"I mean, that hasn't happened since 1906, and I don't think it's going to happen anytime soon," he said.
The Cubs close the regular season with three games against the Red Sox and dropped the first game of a Friday doubleheader. The White Sox finish with three games at home against the Rockies this weekend. They are one game behind the Guardians in the AL Central, but they own the tiebreaker over Cleveland if the teams end tied.
In Other News...
White Sox Prospects Suddenly Face Bigger Questions After A Brutal 2026
The White Soxs prospect watch has taken a rough turn now that the 2026 minor league season is over, and a few of the organizations more notable names left the year with more questions than answers. Right-hander Tanner McDougal spent the season dealing with an injury and a role change, while infielder Jeral Perez had a harder time than expected adjusting to Double-A pitching, two developments that complicate the path the club had hoped to see from both players.
Christian Oppors season added another layer to the concern. The left-hander battled control problems and was eventually demoted, a setback that only deepens the uncertainty around his future role. For a farm system that needs progress, the issue now is not just who struggled in 2026, but which of these prospects can still put themselves back on track inside the White Sox organization. [Read more 🡒]
Colson Montgomery Just Reached A White Sox Milestone Nobody Wanted
Colson Montgomerys rookie season has delivered plenty of loud contact and enough production to keep the White Sox intrigued, even as one particularly unforgiving number now sits at the center of his year. The shortstop set a new club mark for strikeouts in a season, edging past a record long associated with Adam Dunn, while still giving Chicago real value with his power at the plate and steady work in the field.
Montgomery has hit 31 home runs and driven in 87 runs, good enough to rank among the American Leagues better power bats, and his defense has been a plus as well. His plus-10 fielding run value and top-tier outs above average show why the strikeout total does not tell the whole story, even if the milestone itself is the kind nobody in a rebuild wants to celebrate for long. [Read more 🡒]
White Sox Mourn A Pitching Voice Fans Will Never Forget
The White Sox lost one of the most recognizable voices in their modern baseball history with the death of Don Cooper at 70. A fixture in the organization for 33 seasons, Cooper spent 18 years as the clubs major league pitching coach and became one of the defining figures behind a generation of White Sox arms, building his reputation through relentless teaching and a presence that players and fans alike came to know well.
Coopers path to that role started with a brief big league playing career before he moved into coaching, where his influence only grew. For White Sox fans, he was more than a coach on the bench or in the dugout; he was part of the teams identity for years, and his long run in Chicago left a lasting imprint on the pitchers he helped shape and the organization he served. [Read more 🡒]