The Cubs are headed toward the 2026 trade deadline with a clear message: this is a club built to push chips in, not sit on them.
Chicago’s place in the National League Central remains open enough, with the Milwaukee Brewers not having slammed the door shut, and the Cubs are in control of the National League Wild Card race. Add in the aggressive winter Jed Hoyer and Co. had, signing Alex Bregman and trading for Edward Cabrera, and the direction is obvious. The front office is focused on winning now.
That makes the farm system more of a tool than a shield. There are prospects the Cubs should still treat carefully, but this is not the kind of deadline where holding everyone close to the vest makes much sense. After the 2026 MLB Draft, a few names look especially movable.
Josiah Hartshorn, Jefferson Rojas and Owen Ayers are the closest thing to untouchable in the system. Even there, the right deal could change the conversation. But beyond that trio, the Cubs have several prospects who suddenly feel more expendable.
Jaxon Wiggins is one of them. In a perfect world, Chicago would probably prefer to keep him.
Even with Cade Townsend having moved ahead of him as the system’s top pitching prospect, high-end arms are always valuable. Still, if the Cubs go after a starting pitcher before the deadline, the other club will almost certainly want pitching back in return.
Wiggins is the cleanest way for Chicago to meet that ask.
Kane Kepley also fits the profile of a player who could be available. The Cubs used their 2026 draft on pitching, then took outfielder Caden Sorrell in the second round.
Since 2026 draft picks can’t be traded this summer, though they can possibly be included later as a player to be named, Sorrell’s arrival could make Kepley easier to move. The 2025 draftee has put together a .832 OPS in High-A this season, and his speed and defense point to center field.
The issue for Chicago is that Pete Crow-Armstrong appears set there for a long time. With Hartshorn still carrying more keep-worthy power upside, Kepley looks like a player the Cubs could cash in while his start is hot.
Mason McGwire belongs in the same conversation. The Cubs added even more pitching after the 2026 MLB Draft, and that depth gives them room to deal from that area.
McGwire’s profile is trending up after being named to the MLB All-Star Futures Game, and he has struck out 31% of the hitters he’s faced this season across 56 innings between Low-A and High-A. For a seller looking to refill pitching depth anywhere in the organization, McGwire is another name Chicago should not be afraid to move.
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What makes the decision stand out is that Hendriks had been throwing the ball well in the minors, giving Chicago a healthy-looking option to monitor as it sorted through bullpen depth. Instead, the Cubs let him go on July 16, leaving another question hanging over a pitcher whose path has already included rehab assignments, a major league return and another surgery on his right elbow. [Read more 🡒]