Less than a week before the 2026 trade deadline, the Cubs are staring at the same question every contender eventually faces: how hard should they push?
Chicago looks like a playoff team. But it does not look like a club built to breeze past the Dodgers or Brewers, and that changes the kind of deadline swing Jed Hoyer and Carter Hawkins should be willing to take.
A 2016-style blockbuster feels unlikely here. Moving one of the organization’s best prospects for a rental is even harder to picture.
Still, this is a team in the middle of a contention window, and that matters. If the Cubs are going to make a real push, they need to weigh not just this season, but what comes after it too.
That’s where a few names start to feel movable.
Jaxon Wiggins is no longer the obvious untouchable he might have been a year ago. The Cubs’ 2026 MLB draft changed the picture, with 16 of their 21 selections going to pitchers.
On top of that, most prospect evaluators already view Cade Townsend as a better pitching prospect than Wiggins. Chicago probably isn’t eager to include Wiggins in a deal, but for the right controllable arm, he likely wouldn’t be a deal-breaker.
Kane Kepley fits a similar lane. The 2025 second-round pick put up a 180 wRC+ at Low-A last year in 131 plate appearances, and he has kept it going at High-A this season.
He projects as a major-league center fielder, which is exactly why the Cubs can afford to consider him in the right trade. He probably won’t be in play for a rental, but in a bigger deal, he could be.
Pedro Ramirez is another prospect who could be on the move if the right opportunity comes along. There’s a case for keeping him - he’s a switch hitter, he can move around the field, and he could fit into one of the open outfield spots next season. But Matt Shaw brings the same switch-hitting and versatility angle, which makes Ramirez the more likely of the two to surface in trade discussions.
Owen Ayers is the toughest of this group to pry loose, and for good reason. He’s probably close to off limits.
Even so, if the Angels came calling with Jose Soriano or Reid Detmers as the centerpiece, the Cubs would have a hard time turning that down. Outside of a package like that, Ayers should stay put.
On the other side of the board, there are two prospects Chicago should treat as nearly untouchable.
Josiah Hartshorn sits at the top. Of everyone in the Cubs’ system, the 2025 draft pick looks closest to blue-chip status.
He entered the weekend with 16 home runs between Low-A and High-A, plus an OPS of .901. At 19 years old and from both sides of the plate, Hartshorn is exactly the kind of talent the Cubs should be careful not to move.
Jefferson Rojas is right there too. While Hartshorn has grabbed attention, Rojas has quietly been taking on Double-A.
He entered the weekend with an .806 OPS and 14 home runs, and at 21, the shortstop has a very high ceiling. Given the structure of the Cubs’ starting infield, there may come a day when Rojas becomes a tempting trade chip.
This just shouldn’t be that day.
In Other News...
Cubs Bullpen Suddenly Has A Reason For Late-Season Hope
The Cubs bullpen, which has spent much of the summer piecing itself together, suddenly has a few more encouraging health updates to track. Hunter Harvey has resumed bullpen sessions and is expected to begin a minor-league rehab assignment soon, while Daniel Palencia is also moving forward after a strong bullpen session and could be headed for rehab work within the next couple of weeks.
Shelby Miller adds another layer to that late-season picture. The veteran right-hander, coming back from Tommy John surgery, has also resumed bullpen sessions and is on track to pitch for the Cubs before October, with a rehab assignment coming soon. For a relief corps that has needed help all year, the possibility of getting multiple arms back in the mix gives Chicago at least a little reason to look past the current grind and toward what the final stretch might hold. [Read more 🡒]
Cubs Suddenly Face A Deadline Question Fans Wont Like
Cody Bellingers hamstring injury has quickly turned the Yankees outfield depth into a problem, and Aaron Boone has already acknowledged the club may need to look outside the organization for help. With Bellinger expected to miss four to six weeks and other key outfielders also banged up, New York is suddenly in the market for a right-handed bat, the kind of move that can ripple through the trade market well before the deadline.
For the Cubs, that is where the conversation gets uncomfortable. Any team looking for immediate outfield help is going to ask about Chicagos more established hitters, and the Yankees have the kind of need that can push a serious discussion into motion fast. If the Cubs decide to listen, the return would likely have to make sense for a club trying to balance present value with future depth, which is exactly the sort of deadline calculus that can get complicated in a hurry. [Read more 🡒]
Jed Hoyer May Finally Be Ready For A Cubs Deadline Gamble
Jed Hoyer appears to be approaching this deadline with a different level of urgency, and the reason is easy enough to see. Chicagos pitching depth has been tested by injuries, and according to MLB insider Jeff Passan, the Cubs are prepared to move both prospects and major league talent if that is what it takes to bring in starting help before the Aug. 3 deadline. For a front office that has often preferred to protect its future, that kind of flexibility would mark a notable shift in how aggressively it is willing to chase a fix.
The prospect side of the conversation is already getting attention, with names such as Kane Kepley, Jaxon Wiggins, Pedro Ramirez, Jefferson Rojas and Owen Ayers floating as possible trade chips. Chicago has also been linked to some of the bigger arms that could shape the market, including Tarik Skubal, Freddy Peralta and Reid Detmers, which only adds to the sense that this could become a meaningful pivot point for the roster. Josiah Hartshorn is expected to stay put, but the larger question is how far Hoyer is willing to go to strengthen the rotation. [Read more 🡒]