The Chicago Cubs haven’t reached the postseason in four years—but 2025 might be their best shot to break the drought. Sitting atop the NL Central standings just days before the trade deadline, Chicago is “desperately” working the phones to acquire a starting pitcher, according to USA Today’s Bob Nightengale.
“The Cubs desperately want another starter at the deadline, targeting Mitch Keller of the Pirates, and would include outfield prospect Owen Caissie to make it work.”
Bob Nightengale on the Chicago Cubs
With the Phillies breathing down their neck, just a half-game back, the margin for error is razor-thin. Every game feels like October, and Chicago’s front office knows this rotation needs help.
Nightengale reports the Cubs are actively seeking a reliable arm to stabilize their staff heading into the stretch run. That urgency reflects a front office determined to capitalize on its current standing.
One name that’s been floated is Mitch Keller, a 29-year-old All-Star-caliber righty currently with the Pirates. Keller is enjoying a career year, with a personal-best 3.53 ERA across 125 innings, showcasing improved control and durability. He’s under contract through 2028, making him an ideal long-term fit if acquired.
But prying him loose won’t be easy.
To get a deal done, Chicago might have to part with elite prospect Owen Caissie. Ranked No. 36 overall by MLB Pipeline and No. 1 in the Cubs system, Caissie is seen as a foundational piece of the future. Moving him would send a clear message: The Cubs are ready to win now.
That message would undoubtedly resonate with fans who’ve watched this team flirt with contention before only to fall short. With a roster that includes sluggers like Seiya Suzuki and Kyle Tucker, plus a top-ranked bottom of the order in terms of OPS and batting average, Chicago has the bats. It’s the arms that need reinforcement.
Adding a workhorse like Keller—or another comparable starter—would signal that the Cubs aren’t just trying to make the playoffs. They’re building to go deep.
With just days left until the deadline, the eyes of Wrigleyville turn to the front office. Will they make the bold move? Will the drought end?
Stay tuned.
