The White Sox walk into Wrigley Field with momentum, a division lead, and a chance to keep turning a surprising season into something even bigger. At 65-58, Chicago sits 5.5 games ahead of the second-place Detroit Tigers in the AL Central after coming off a 121-loss season just two years ago. Now comes a Crosstown test against a Cubs team that is 72-53 but still trails the Milwaukee Brewers by 5.0 games in the NL Central.
This is a very different version of the matchup than the one the White Sox won at Rate Field back in May. Both clubs have changed since then, and both were active at the trade deadline. The White Sox have been surging since May, while the Cubs have spent much of the year swinging between hot streaks and cold ones.
For Chicago, the biggest issue is the pitching plan behind the opener. The White Sox are without a true fifth starter, and Davis Martin’s injury has left two rotation spots open. Luis Castillo is set to start Monday, but Tuesday and Wednesday are listed as TBA.
If nothing changes, Erick Fedde and José Urquidy are the most likely candidates to take those starts. That would put extra strain on the bullpen, and it is not the cleanest setup for a series this important. Fedde and Urquidy have both struggled, so the White Sox would be asking for trouble if they have to lean on both of them here.
There are alternatives if the club decides to make a move. Drew Thorpe could be added to the major league roster during the series to make his first start since 2024.
Johnathan Cannon or Shane Smith could also be elevated. However it shakes out, the White Sox need an answer quickly.
The Cubs’ rotation does offer some openings of its own. Shota Imanaga, who is scheduled to start Monday, has been rough in two starts against the White Sox. In July of 2025, he allowed seven runs in just three innings against them, and Chase Meidroth and Colson Montgomery each homered off him.
Tuesday brings Kevin Gausman, and his last outing after being acquired at the deadline was a mess. He gave up six runs in 4.2 innings against the Washington Nationals.
Wednesday’s starter will be Clay Holmes, who has been solid since returning from injury. In two starts with the Cubs, Holmes has a 3.38 ERA.
Even so, he is the type of pitcher the White Sox can put balls in play against, and they’ll need to take advantage.
That brings the spotlight to Colson Montgomery, who is starting to show signs of escaping a prolonged slump. He remains one of the biggest keys in the White Sox lineup.
When he’s going, the offense can look unstoppable, but over his last seven games he is hitting just .179/.233/.321. That won’t get the job done in a series like this.
The good news for Chicago is that Braden Montgomery, Miguel Vargas, and Tristan Peters have recently broken out of slumps. If Colson Montgomery can join them, the White Sox give themselves a much better shot at stealing another Crosstown Classic from the Cubs.
It’s a series that could shape both seasons, and there’s no shortage of pressure on either side.
In Other News...
White Sox Made A Catching Choice Fans Wont Ignore
The White Sox wrapped up a productive week at 4-2, with enough pitching and timely power to keep the momentum moving in the right direction. Luis Castillo delivered a quality start, Jos Urquidy helped steady the staff in relief, and the lineup got home runs from Tristan Peters, Munetaka Murakami and Miguel Vargas during the series against the Detroit Tigers.
Amid all that, the club also made a catching move that will draw immediate attention. Chicago added Jake Rogers to the roster and sent Edgar Quero to Charlotte, a decision that reshapes the depth chart at a position that always tends to get watched closely, especially when a young player is involved and the team is trying to sort out its next look behind the plate. [Read more 🡒]
Caleb Bonemer Is Giving White Sox Fans Another Reason To Believe
Caleb Bonemer keeps stacking up reasons for White Sox fans to keep an eye on the farm system, and the latest recognition came from Baseball America, which slotted him 15th on its Hot Sheet after a strong week at Double-A. Since the promotion, Bonemer has looked more than comfortable, posting a .381/.519/.810 line and showing better contact skills along the way, a promising sign for a club still trying to build its next wave from within.
For Chicago, the encouraging part is not just the production, but the way it fits the bigger picture of the organizations minor league pipeline. The recent round of affiliate action also brought a full slate of game recaps and individual stat lines from Rochester, Columbus, Winston-Salem, Greensboro, Kannapolis and Hickory, offering another snapshot of how broad the rebuild effort has become, with Bonemer now standing out as one of the names worth tracking most closely. [Read more 🡒]