The Chicago White Sox have been the best story of baseball this season and are seemingly in the first year of an extended stretch of contention. The Chicago Cubs, meanwhile, entered the season with high expectations after adding Alex Bregman and, at 72-53, are one of the true threats to win the NL and make it back to the World Series.Â
Now, the two are set to square off at Wrigley Field on Monday to kick off what should be a thrilling rivalry series. Which begs the question: With both teams likely headed to the postseason, what weakness must each fix before the playoffs begin? Let’s dive into it.
Chicago Cubs: Replacing Dansby Swanson

At the trade deadline, the Cubs’ priority was pitching, pitching and more pitching. They added Clay Holmes, Kevin Gausman, Braxton Garrett and Ryan Zeferjahn. They just got Edward Cabrera, their prized offseason acquisition, back from the Injured List — but after another rough outing and a blister issue, the team is considering moving him to the bullpen.
So yes, there are still questions in the rotation and bullpen. But the biggest question the Cubs face now is the health of Dansby Swanson and how the team will replace its stalwart shortstop
Swanson is expected to be sidelined 4-6 weeks with an oblique injury, a devastating blow to the Cubs’ world-class infield defense. The initial thinking is that Nico Hoerner will see more opportunities at shortstop while infielders Pedro Ramirez and Matt Shaw, who is currently on the Injured List, will see more action as well.
The good news for the Cubs is that Swanson is expected to return before October. But his defense, and his bat (18 home runs and 66 RBI), are crucial elements to the franchise and its World Series aspirations. So as long as he’s sidelined, that’s the biggest question surrounding the Cubs. He’s that important to the organization.
Chicago White Sox: Finding stability at catcher

What the White Sox have done this season is remarkable. Chris Getz has pushed all the right buttons to get the organization to this point, and the coaching staff, headlined by manager Will Venable, has done a masterful job.
But the biggest question surrounding the White Sox is … who’s going to be the catcher?
This was a priority for the White Sox at the deadline, and they had plenty of conversations with other teams. Tyler Stephenson was a player of interest, but the price tag was far too high for the organization (and for other contenders, too). They ultimately acquired Joey Bart, a former top prospect, in a trade with the Atlanta Braves, only for him to suffer a fractured hand almost immediately.
Chicago then added veteran catcher Jake Rogers, who is now on his fourth team in 21 days. It’s been a whirlwind for Rogers, who was Tarik Skubal’s personal catcher in Detroit. He’s hit only .176/.281/.315 with a .596 OPS, three home runs and 11 RBI in 41 games this season.
Rogers, 31, will now step into a prominent role with the White Sox. His defense and ability to call games behind the plate will help a young pitching staff. But they’ll need production at the plate, too, for Rogers to keep the job the remainder of the regular season and into the postseason.
