The Chicago White Sox enter Saturday’s Crosstown Classic matchup at Guaranteed Rate Field looking to flip the narrative in what has otherwise been a lopsided 2025 season, as they sit at 36–65 and well out of contention in the American League. Still, there’s a renewed sense of competitiveness post–All-Star break, with manager Will Venable’s squad showing more life and covering the spread in seven of their last ten games as sizable underdogs—a trend that gives oddsmakers and bettors alike reason to take notice. The White Sox will send Aaron Civale to the mound, a veteran right-hander with a 2–6 record and 4.76 ERA who has struggled with control and inefficiency in recent outings. While Civale’s command hasn’t been sharp, he’s capable of navigating lineups through soft contact when he’s locating his cutter and curveball, and the Sox will need him to avoid the early-game blowups that have doomed many of his recent starts. Offensively, the White Sox are led by Luis Robert Jr., whose speed and bat-to-ball skills remain elite, and Miguel Vargas, who’s turned in a solid second half with timely extra-base hits. Rookie Colson Montgomery has also emerged as a bright spot, showing maturity in his plate approach and flashing gap power that gives Chicago some optimism for the future. Complemented by the versatile Chase Meidroth and improving defense up the middle, the White Sox are slowly becoming more cohesive, even if the results haven’t consistently translated into wins.

Their bullpen, shaky for much of the year, has actually improved in the second half, with late-inning arms like Jared Shuster and Steven Wilson providing some stability, which has helped them remain competitive in closer games. The Cubs will present a stiff challenge, especially with Cade Horton on the mound and an offense headlined by Kyle Tucker and Pete Crow-Armstrong, but the White Sox do tend to perform better when expectations are lower and the energy at home is high. Defensively, they’ve reduced their error count and played more fundamentally sound baseball, which has helped keep totals close despite facing superior opponents. From a strategic standpoint, Venable will likely lean into small ball and aggressiveness on the bases to pressure Chicago’s defense, particularly if Civale can give five innings with minimal damage. Offensively, the Sox will need to string together hits against Horton early before the Cubs’ bullpen shortens the game, as late comebacks have been rare and tough to mount against Chicago’s setup men and closer. While the odds are clearly stacked against them, the Sox have shown a feisty underdog spirit lately, and a close, low-scoring affair could allow them to hang around longer than expected, especially if Civale can induce ground balls and stay ahead in counts. Their recent ability to cover as +160 or worse underdogs suggests this may not be a blowout, and if the offense can seize momentum with a few early extra-base hits, Saturday could offer a rare bright spot in a rebuilding season that has mostly been defined by growing pains and learning experiences.