As the Chicago Cubs continue searching for ways to strengthen an already competitive roster ahead of the trade deadline, they may suddenly find themselves facing unexpected competition from a familiar rival. For much of the season, the focus has been on what moves the Cubs could make to bolster their postseason aspirations, but a surprising report suggests the Chicago White Sox could also enter the market as buyers, potentially complicating the Cubs’ pursuit of top talent.
Few people would have predicted before the season that the White Sox would be in a position to add pieces at the deadline. While both Chicago franchises have experienced ups and downs in recent years, the Cubs have consistently remained the more stable and competitive organization. The White Sox, meanwhile, have endured several difficult seasons that left many questioning the direction of the franchise.
With the deadline approaching, however, circumstances could create an intriguing battle between the two clubs. According to ESPN insider Jeff Passan, both teams could emerge as potential suitors for Miami Marlins ace Sandy Alcantara.
“Teams are far more bullish on Alcantara this deadline than they were last time around, when the gap between the Marlins’ ask and others’ willingness to give up significant talent was too large to bridge. With just this year and a club option for less than the qualifying offer remaining, the 30-year-old Alcantara throws hard, eats innings and induces ground balls,” Passan wrote.

The possibility of the White Sox entering the bidding is certainly noteworthy, especially for the Cubs. Chicago’s North Side club has legitimate playoff ambitions and could view Alcantara as a major addition to its rotation. Any increase in competition for one of the market’s most coveted pitchers could make negotiations more challenging.
The White Sox possess a growing collection of young talent that could make a deal easier to construct, though whether they are prepared to make a major splash remains uncertain. A blockbuster acquisition may not perfectly align with their current timeline, but their reported interest adds an unexpected wrinkle to the deadline landscape.
For the Cubs, the development is one worth monitoring closely. As they look to strengthen their roster for a postseason push, they may have to fend off not only contenders around the league but also their crosstown rivals in the race for one of baseball’s most intriguing trade targets.