The White Sox and Cubs are both over .500 entering the Crosstown Classic, giving Chicago baseball its most meaningful rivalry series in nearly two decades.
The 2026 Crosstown Classic between the Chicago White Sox and the Chicago Cubs is here, and it has been a long time since this series was this highly anticipated.
Now, of course, anytime these two teams step between the lines to play one another, there is a different sense of intensity and pride for both the players and the fans. Over the years, that has led to some pretty memorable moments.
There was Christopher Morel’s walk-off three-run homer at Wrigley Field back in 2023. There was a go-ahead blast by Eloy Jimenez in 2019, with Jason Benetti’s voice belting out, “Thanks, Cubs!” across the White Sox broadcast.
There was a walk-off home run by Aramis Ramirez during the 2008 series at Wrigley Field.
And of course, there was the 2006 brawl between A.J. Pierzynski and Michael Barrett after Barrett threw punches when Pierzynski crossed home plate. Just a month or so later, Pierzynski launched a game-winning, go-ahead three-run shot in the ninth inning at Wrigley Field, getting his revenge with one swing.
Perhaps the stage is set for more memorable moments to be made this weekend.
Even when you look back on those iconic moments from the last 20 years, the ones that hit the hardest are probably from 2006 and 2008. That stems from the fact that we had competitive baseball in Chicago pouring gasoline on this rivalry.
While the Cubs were not competitive in 2006, the White Sox absolutely were. They were also coming off their 2005 World Series title, which obviously was not a pleasant sight for Cubs fans, who at the time were still dealing with the longest championship drought in professional sports.
By 2008, the Cubs had put together another playoff team. The White Sox rolled into Wrigley Field with a 41-32 record, sitting 3.0 games up in the AL Central. The Cubs sat at 45-28 at the time with a 3.5-game lead in the NL Central.
Two teams over .500 and two first-place ballclubs. Both the Sox and Cubs went on to win their division that year.
Funny enough, that series in June 2008 was the last time the Cubs and White Sox faced each other when both teams were above .500 and fans were allowed in the stands. The only exceptions was the 2020 pandemic season. We have been in a drought when it comes to getting a truly competitive Crosstown Classic, largely because the White Sox have not been holding up their end of the bargain.
But after a sweep of the Kansas City Royals this week, the White Sox now sit with a 22-21 record. They are currently in a playoff spot in the American League and just 1.0 game back of the Cleveland Guardians for first place in the AL Central. The Cubs sit at 28-16 with a 2.5-game lead over the Milwaukee Brewers in the NL Central.
Two teams over .500, two teams holding a playoff spot, and a stage set for actual stakes and an actual rivalry.
As of now, many teams in baseball, the Cubs included, may not be taking the White Sox all that seriously. You see a 22-21 record and think, "that’s cute." And to be fair, it has been difficult for Cubs fans to have much resentment toward the White Sox with how the Southsiders have fared over the last three seasons.
But the White Sox have every intention of proving themselves this weekend. And as White Sox starting pitcher Sean Burke said, they have their eyes on being the best team in the city.
“I think we obviously have the rivalry going, and we want to be the best team in the city,” said Burke, who will take the ball for the White Sox on Friday night.
White Sox shortstop Colson Montgomery was not able to hold back his excitement either.
“We are all fricking looking forward to it. We are all hyped up. They are a really good team. We know we are a really good team. It’s going to be fun,” he said.
The White Sox definitely have more to gain from a confidence standpoint this weekend, but they also have more to lose. And while many Cubs fans may not view this as a heated rivalry right now, if the White Sox have success against the Cubs this weekend, pushing themselves even further up in the AL standings and giving Sox fans a leg to stand on, the intensity of the rivalry only ticks up.
But even the fact that we are having this conversation and getting ready to watch the first game between the White Sox and Cubs where both teams are above .500 since 2008 shows you what a great time it is to be a baseball fan in the city of Chicago.
And if the White Sox keep ascending in the direction we think they are, we have plenty more of these series in front of us. This might be as tame as things get in the years to come.