The Chicago Cubs have yet to make any truly significant moves this offseason, which has drawn the ire of Cubs fans who are growing tired of the front office becoming so stagnant.
While Chicago is a huge city, the Cubs have certainly not operated like a large-market franchise in recent years, so when they don’t make any major additions, the fan base is more frustrated than surprised.
And perhaps Chicago fans should be prepared to get frustrated again.
It’s no secret that the Cubs could use another starting pitcher, especially with such little pitching depth in their farm system and with a chunk of their rotation slated to hit free agency after 2026. But Chicago missed on Tatsuya Imai, and its trade market is slowed to a crawl.
Why? Because the Cubs seem to be unwilling to budge on their top prospects.
Chicago Cubs are hitting a roadblock in trade discussions
Sep 13, 2025; Chicago, Illinois, USA; Chicago Cubs right fielder Owen Caissie (19) looks on from the dugout prior to a game against the Tampa Bay Rays at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images
Chicago has been floated as a potential trade destination for Miami Marlins pitcher Edward Cabrera as well as Washington Nationals hurler MacKenzie Gore. Other names have been mentioned, as well, both those seem to be the top two most likely targets.
But do the Cubs even have a chance to land either arm?
Not if they aren’t willing to pay the price, and Jordan Bastian of MLB.com questions whether or not Chicago would actually be amendable to parting with top young players like Matt Shaw, Owen Caissie or Moises Ballesteros in a trade.
“Chicago could perhaps thread the needle and solve both goals by exploring the trade market (Marlins righty Edward Cabrera comes with three years of control via arbitration, for example),” Bastian wrote. “That would hypothetically require being more open-minded to trading away a young player such as Shaw, Caissie or catcher Moises Ballesteros. The Cubs were unwilling to do that at the Trade Deadline last summer, when they looked into impact arms on the market.”
The problem is that in order for Chicago to land any talented young pitcher with multiple years of club control remaining, it will have to get aggressive and be willing to dig into its farm system.
The Cubs won 92 games in 2025 and absolutely had a World Series-caliber roster. They are in win-now mode, and most of their top prospects are position players. Cashing in some of those for a pitcher would not be the worst idea in the world, and given Chicago’s current pitching situation, it might actually be advisable.
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