White Sox, Cubs Pitted Against Each Other in MLB Free Agency

The Chicago White Sox were the talk of baseball in 2026, putting together a surprising 84-78 campaign that resulted in a playoff berth.

With that breakout season came a much more competitive and compelling baseball environment in the city of Chicago. Both the White Sox and their crosstown rivals, the Chicago Cubs, were in a pennant race. It's one of the few instances in history where that's been the case.

In fact, 2026 marked just the fourth time in history that the Cubs and White Sox made the playoffs in the same season.

Now, ironically, the two franchises find themselves with similar needs to address this offseason.

The White Sox had the fewest innings pitched by starting pitchers in baseball last season, and by the time the postseason came around, right-hander Sean Burke was Chicago's only reliable starter.

While the Sox have plenty of young pitching depth, there's a need to add frontline arms who can complement Burke atop the rotation and take the ball in a playoff game.

The Cubs, on the other hand, need to replace their losses. Matthew Boyd, Shota Imanaga, Clay Holmes, and Kevin Gausman are all free agents. Ben Brown is undergoing cervical spine surgery and won't be available for the start of the regular season.

The Cubs need frontline arms much like the White Sox do. But volume will also be a point of emphasis for the North Siders as they look to fill out an otherwise depleted starting rotation.

Two teams playing in the same city, each with similar needs. And according to the latest reports, the White Sox and Cubs may find themselves fighting over the exact same players.

MLB insider Bruce Levine believes that Japanese right-handed pitcher Kaima Taira is the top priority for both clubs right now. Both Chicago teams met with Taira's agent, Scott Boras, during the GM meetings in Las Vegas, and a deal is expected for Taira at some point before the lockout on December 1.

Even broadening the scope a little bit, it's hard to imagine the Cubs won't show some level of interest in the very same arms the White Sox have already been linked to. Freddy Peralta, Sonny Gray, and Dustin May are all pitchers the White Sox are considering, and the Cubs are one of the teams that have specifically expressed interest in May already.

After a fairly even fight on the field during the Crosstown Classic in 2026, the rivalry between the White Sox and Cubs is expanding into the offseason.

Luring a free agent to Chicago is only one part of the challenge. The White Sox will also have to convince their pitching targets to sign with them over the Cubs.