The Chicago Cubs are expected to be buyers at the 2026 trade deadline, and if you’ve been around this sport long enough you know what that means. Somebody’s walking out the door who the front office actually likes.
Two names keep coming up in conversations with scouts and rival execs: right-hander Jaxon Wiggins and outfielder Kane Kepley. Neither guy is being shopped because the Cubs have cooled on them. But both fit the kind of profile that makes a selling team say yes, and that’s usually how these things work.
Wiggins Is the Easy Fit in a Pitching Deal
The Cubs would love to keep Wiggins. He’s their No. 3 prospect even after Cade Townsend jumped him on the organizational depth chart, and anyone who watched his rehab start in High-A on June 28 saw why. 3.2 innings, two hits, no runs, no walks, four strikeouts. Fifty-seven pitches, 39 strikes. He looked sharp.
But here’s the thing about deadline deals for starting pitching. If you want a proven arm, the team on the other end almost always wants a pitcher back. Not necessarily one who can help tomorrow. Just one with the ceiling to matter eventually. Wiggins is that guy. He gives Chicago a way to land a rotation upgrade without touching the absolute top of the farm system.
Nobody’s saying the Cubs are eager to move him. But when you’re chasing a playoff spot and the phone rings, Wiggins might be the answer to the question the other side is asking.
Kepley Has a Numbers Problem
Kane Kepley’s situation is different. It starts with the draft. The Cubs used their second-round pick this year on outfielder Caden Sorrell, and while 2026 draftees can’t be traded until later, the pick tells you something about how the organization sees its outfield pipeline. They added another one on purpose.
Kepley himself has been great. The 2025 second-rounder is hitting .832 OPS at High-A with five homers through early July. He’s fast, he plays a legitimate center field, and he’s been on base in 13 of his last 14 games. The problem isn’t him. It’s Pete Crow-Armstrong, who has center field locked down in Chicago for the foreseeable future.
That leaves Kepley stuck behind a guy who isn’t going anywhere. Meanwhile another outfield prospect, Hartshorn, looks safer from trade talk because his power profile gives him a different path to the big leagues. Kepley doesn’t have that separation. He’s a center fielder on a team that already has its center fielder.
So the math gets simple. Kepley’s stock is high right now. His path is blocked. And the Cubs have to decide whether to cash in or let his value sit and wait.
Both Wiggins and Kepley are talented enough to be real trade chips, but the roster ahead of them makes them moveable in a way that the truly untouchable prospects aren’t. If Chicago is serious about adding pitching before the deadline, these are two names that are going to keep popping up. The Cubs might not want to trade them. But wanting to keep a player and being able to keep a player are two different things in July.
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