Chicago Cubs face brutal trade deadline dilemma

Any acquisitions made from this point forward have to serve two duties: Help the Cubs win now and help the Cubs win in the future.

That’s why Cubs president Jed Hoyer and the front office have an extra tough job between now and the August 3 trade deadline. The team simply doesn’t have the prospect capital to waste on three-month rentals. They need to put their tradeable prospects toward players who will be around beyond 2026.

Matt Shaw, who has probably shown that he deserves a shot at one of the corner outfield spots left behind by Happ or Suzuki, is the biggest asset the Cubs have when it comes to trade bait. And he offers their best bet at landing a good, young pitcher for a staff that will be emptied by free agency and also rattled by injury, even well into next season.

Per Bleacher Nation’s Michael Cerami:

“I actually believe in Matt Shaw more today than I did last season, both offensively and defensively (that wasn’t even his only good defensive play last night). HOWEVER, I think there probably is a scenario in which trading him makes sense, and that’s for the equivalent pitcher version of Shaw on some other team. I don’t know if that actually even exists (would the Red Sox even move Connelly Early or Payton Tolle anymore? I’m not so sure). But if it does, that’s where you have to think about it. The lack of pitching right now might be an injury problem. But next year, it’s an injury problem AND a … a bunch of guys left in free agency problem. Can’t get it all done in the offseason. Just not possible.”

No one should be off-limits

The Cubs shouldn’t be holding any prospect as off-limits. At this point, facing the situation they’re facing, everyone should be on the table if it means, specifically, acquiring pitchers who could actually be healthy and effective contributors for the rest of 2026 and into 2027 and beyond.

Of the pitchers fitting that bill—possibly available at the deadline—are: Logan Webb, Reid Detmers, and Jose Soriano, who are under contract through the 2028 season, and Joe Ryan, Sandy Alcantara, and MacKenzie Gore, who will become free agents at the end of 2027.

Facing the very real possibility that next year’s starting rotation could be manned entirely by health risks coming off injury-ravaged seasons (Cade Horton, Justin Steele, Edward Cabrera, Ben Brown), Chicago desperately needs some stability in that area. Maybe they might bite the bullet this offseason on one major free agent pitching acquisition, but they’re still going to need more.

If the Cubs are serious about contending beyond this season, they’ll have to make some uncomfortable trade decisions with their young talent. They’ll have to be ready to deal away some of their long-term future for the sake of their more immediate future.