MLB.com predicts which Cubs top prospect is likeliest trade deadline chip

Considering they’re one of the best teams in Major League Baseball, it’s not hard to believe that the Chicago Cubs will be buyers at the trade deadline. They might be one of the more active buyers, considering a case can be made that they need both starting pitching and relief pitching.

They don’t seem to need offense, and at least in part because of this, it’s expected that outfield prospect Owen Caissie could be on the move.

Jordan Bastion of MLB.com definitely believes that Caissie could be the most intriguing trade chip for the Cubs at the deadline. And there’s a very good reason why the insider believes he will be at the top of the list of prospects on the move from Chicago’s fairly deep farm.

Owen Caissie emerges as Cubs’ prime deadline bait amid search for rotation and bullpen help

“The Cubs’ big league outfield and designated hitter jobs are taken,” Bastion wrote, “making Caissie a depth piece who can hope a route to Chicago opens in 2026. The outfielder boasts strong power potential with solid on-base ability. If the Cubs want to add an impact piece at the deadline, teams might be enticed by Caissie as a near-MLB-ready change-of-scenery candidate.

This isn’t the first time Caissie has been mentioned as a top trade chip. It was almost a month ago that Joel Reuter of Yahoo Sports made the same observation. 

Considering that it's the team's top priority to have Kyle Tucker locked in long-term, Ian Happ is in town through the end of next year, Pete Crow-Armstrong is emerging as a legitimate MVP candidate, and Seiya Suzuki is posting the best offensive season of his career, there isn’t a spot for Caissie until at least next year.

The Cubs also have other outfielders who could be ready for 2026, should Tucker or another big free agent signee not fill the right field or DH spot next season. Kevin Alcantara remains a high-upside option, and both James Triantos and Jonathon Long have gotten reps in the outfield corners this year. One of the points of having a deep farm is to ensure a club can fill openings quickly.

Another reason to have a deep farm system is for teams like the Chicago Cubs to be able to trade talented players for players of need for a playoff push. With Owen Caissie posting a solid but not spectacular stat line(.254/.357/.477, .834 OPS), Jed Hoyer could see the outfielder as expendable, esepcially if a long-term upgrade becomes available for the rotation.