At this point in the season, there are no moral victories for the Chicago White Sox, especially with Crosstown bragging rights on the line in front of a raucous crowd of more than 40,000 at Wrigley Field.
Still, Monday’s 7-5 loss to the Chicago Cubs in extra innings offered another reminder that this 2026 White Sox team can go toe-to-toe with anyone, while simultaneously exposing some of the flaws that could ultimately stand between them and a deep postseason run.
The White Sox had no business being in position to win the game, let alone push it to extra innings. They fell behind 2-0 after just five pitches on back-to-back home runs from Pete Crow-Armstrong and Seiya Suzuki, were outhit 14-4, and committed two errors, one of which directly led to a run.
But the White Sox bats have proved all season that they are never more than one swing away from getting back into a game, and Monday was no different. Miguel Vargas snapped a hitless start with the White Sox’s first hit of the game, lining a single after a leadoff walk to Munetaka Murakami. Randal Grichuk then followed by launching a three-run homer 404 feet to center field off a Shota Imanaga splitter, flipping a 2-0 deficit into a 3-2 lead.
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The White Sox offense would not record another hit until the eighth inning, and by then, the Cubs had already retaken the lead thanks to a throwing error by Vargas in the fifth, which allowed two runs to score.
But once again, all it took was a leadoff walk from Murakami to spark the White Sox offense. Andrew Benintendi was called upon to pinch-hit for Grichuk one batter later and picked up right where Grichuk left off, sending the first pitch he saw from Cubs reliever Ryan Zeferjahn into the right-field basket for a go-ahead two-run homer.
The White Sox clearly embraced the playoff-like atmosphere, another trait they have shown time and time again this season. The bigger the stage and the tougher the opponent, the more this young team seems to rise to the occasion.
But unfortunately, the game also exposed some of this team’s warts, serving as a reminder that the White Sox still have work to do if they want to be viewed as a legitimate MLB contender rather than simply a fun underdog story.
Luis Castillo was chased from the game after 4.2 innings, after allowing four runs on eight hits, in a start where the White Sox desperately needed some length. With an already taxed bullpen and an opener scheduled for Tuesday, Chicago could ill afford another abbreviated outing, especially from a pitcher acquired at the trade deadline specifically to help solve that problem.
The White Sox rotation has now failed to have a starter reach the sixth inning in four consecutive games, a stretch that also included an opener against the Detroit Tigers on Friday, leaving several high leverage arms unavailable for Monday.
That put the bullpen in a difficult spot late in the game, with rookie Hagen Smith, who has fewer than five innings of major league experience, being thrust into the 10th inning and tasked with navigating the top of the Cubs’ lineup with the winning run in scoring position.
The already daunting challenge became even tougher when Will Venable elected to have Smith pitch to Pete Crow-Armstrong, who had already collected three hits on the night and continued to make his case as an MVP candidate.
Rather than bypassing PCA, Venable instead opted to roll the dice on a lefty-lefty matchup, avoiding the potential double-play opportunity with Seiya Suzuki waiting on deck. The gamble backfired almost immediately. Smith hung a slider, and Crow-Armstrong launched it 391 feet down the right-field line for a walk-off homer, the first run Smith has allowed in his young major league career.
Venable stood behind the decision after the game, saying he preferred the matchup with Crow-Armstrong and would have intentionally walked Suzuki had Smith recorded the out. While it’s easy to play armchair manager after the fact, the move is one of several questionable decisions Venable has made in tight games this season.
There is no denying Venable has done an excellent job at the helm this season. He has established a clear winning culture, navigated playing time in a deep lineup without allowing veteran egos to become an issue, and kept the team afloat despite persistent shortcomings in the starting rotation. But at the same time, some of his inexperience as a manager has shown.
He has consistently leaned on favorable matchups, which is fine to an extent, but at some point, especially in the postseason, the man-analytics have to take over. There is no excuse to pitch to PCA in that situation just because there is a lefty on the mound, especially a rookie. Crow-Armstrong’s OPS against left-handers is .906 on the year, and he lives for the big moments.
All of this could have been avoided if Jordan Hicks had done his job and locked down the save in the ninth inning. While Hicks shoulders the bulk of the blame after issuing a pair of costly walks, the White Sox ABS challenge issues this season loomed large on Tuesday.
The club’s 46.7% success rate on challenges is the third-worst mark in the MLB. It’s not just that the White Sox lose challenges; they often use them up early in games. That approach is partly rooted in the White Sox’s philosophy of being aggressive and using every tool at their disposal, with the thinking that another opportunity to challenge might not come later in the game. But that approach has burned them time and time again, and Monday was no different.
Hicks dotted the corner in a full count to Ian Happ in the ninth, in what should have been the second out of the inning. The only problem was, the pitch was called a ball, and the White Sox entered the ninth with just one challenge, a challenge that was burned on the previous at-bat.
As a result, the Cubs’ win probability saw a 13% swing and put the tying run in scoring position.
Ultimately, Monday’s loss felt less like a missed opportunity and more like a warning shot. The White Sox showed they have enough firepower, resilience, and toughness to hang with one of the better teams in baseball, but they also exposed the margins that can separate a contender from a team that simply makes the postseason.
The talent is there, but the White Sox are running out of time to clean up the mistakes that could ultimately cost them when the stakes get even higher.
