The Chicago Cubs are not sitting still—and neither is their front office. As the team battles for control of the NL Central, front office executives have been working the phones relentlessly, preparing a series of pitching trade proposals that could define the rest of the 2025 campaign. With the trade deadline creeping closer and playoff expectations surging, the Cubs are going full throttle in their efforts to upgrade the pitching staff from top to bottom.
Multiple sources around the league confirm that Chicago is engaged in trade talks with no fewer than five teams, aiming to acquire both frontline starters and high-leverage relievers. While Sandy Alcantara of the Marlins is clearly the headline target, the Cubs are not limiting themselves to just one major splash. Insiders say they’re attempting to pull off a series of moves—some big, some under-the-radar—to solidify a staff that has shown signs of vulnerability in recent weeks.
With Shōta Imanaga continuing to dominate and Justin Steele returning to form, the Cubs have a strong one-two punch at the top of the rotation. But the back end has been inconsistent, with Jameson Taillon and Jordan Wicks battling injuries and performance dips. The bullpen, while improved, still lacks the depth needed to withstand the rigors of a postseason run. The front office’s aggressive posture is driven by the belief that the Cubs are on the verge of something special—if the arms can hold up.
Among the names being discussed are Detroit’s Jack Flaherty, Oakland’s Paul Blackburn, and Seattle’s Logan Gilbert. All three could slot immediately into the rotation and give manager Craig Counsell the kind of flexibility and matchup control he thrives on. Meanwhile, bullpen help is also on the radar. The Cubs are believed to have inquired about Kansas City’s James McArthur and Miami’s Tanner Scott—two power arms that could transform the late-inning strategy.
What makes this surge of trade activity so notable is the Cubs’ willingness to deal from their depth of young talent. Chicago’s farm system is still among the best in baseball, and players like Kevin Alcántara, Owen Caissie, Moises Ballesteros, and Michael Arias have drawn interest across the league. It’s a delicate balance between building for the future and capitalizing on a golden opportunity in the present, but all indications point to the Cubs prioritizing the now.
General Manager Carter Hawkins and President Jed Hoyer have made it clear: this isn’t a year for half-measures. The energy inside Wrigley Field has shifted. The fans believe again. The players believe again. And perhaps most importantly, the front office believes this team can win it all—with the right reinforcements.
If the Cubs can land even two of their targeted pitchers, it could change the complexion of the NL entirely. A rotation of Imanaga, Steele, and another top-tier arm, backed by a fortified bullpen, would give Chicago the firepower to go toe-to-toe with any team in baseball. And with a balanced offense led by Dansby Swanson, Cody Bellinger, and Seiya Suzuki, the Cubs have few weaknesses when everything is clicking.
The next few weeks could define this season—and perhaps this era—of Cubs baseball. One thing is certain: the front office isn’t backing down. They’re all-in, on all fronts. And if these trades come to fruition, Wrigleyville might just be preparing for another deep October run.