Chicago got a rare double dose of October baseball on Thursday afternoon, and the timing made it even wilder.
The White Sox were first to lock in their spot, rolling past the Kansas City Royals 9-1 to clinch a playoff berth. For a team that’s just two years removed from a 121-loss season and also came off a 100-loss year last season, that kind of turnaround stands out. It also marks the White Sox’s first trip to the postseason since 2021, which makes this stretch feel like quite the half-decade for the club.
Then the Cubs followed not long after, beating the Miami Marlins 2-1 to grab a wild card berth and secure a second straight postseason appearance. The bigger twist: the two Chicago teams clinched on the same day for the first time in city history, and they did it just two minutes apart.
That adds another layer to a season that already had a bit of Chicago baseball history attached to it. This is the fourth time both teams have reached the playoffs in the same year, with the previous instances coming in 1906, 2008 and 2020.
Now the city gets to wait and see whether this remarkable day can lead to something even bigger. If the White Sox and Cubs ever met in the World Series again, it would only be the second all-Chicago Fall Classic. The first came in 1906, when the White Sox beat the Cubs in six games.
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 🡒]