Three Cubs Prospects Who Will Be Prime Trade Chips This Offseason

Following their embarassing sweep at the hands of the San Diego Padres in the Wild Card Round, the Chicago Cubs are in full offseason mode. They have several impending free agents, meaning this is a roster that could (and should) look fairly different in 2027. But in addition to free agency, the Cubs could look to their farm system to help bring in some proven big league talent.

The prospect pipeline isn't in a great spot, but it's also far from dry. With the hope of competing again in 2027, here are three prospects who could wind up on the move this winter.

All prospect rankings courtesy of North Side Baseball.

Kane Kepley, OF

Kepley ranks as the Cubs’ No. 5 prospect, and I think his higher floor would make him an attractive target for other teams looking to add young talent.

Across 125 games between High-A and Double-A this season, Kepley posted a .422 on-base percentage and an .823 OPS. He drew 120 walks, good for a 20.2% walk rate, showing an impressive ability to work counts and get on base. And when he gets on, he’s going to run. He stole 70 bases this season, adding another valuable tool to his profile.

Kepley also projects as a strong defender at the major-league level, giving him several ways to contribute even if he doesn’t have 25-homer upside laden in his bat.

I’m certainly not suggesting the Cubs should move him for just anyone. His combination of on-base skills, speed, and defense gives him a legitimate chance to become a productive big-league player. But if Chicago can use him to land a quality starting pitcher or more immediate outfield help, it may be a move worth making.

Ethan Conrad, OF

Sticking with the young outfielders, Conrad ranks just behind Kepley as the organization’s No. 6 prospect. Like his fellow outfielder, he has a relatively high floor, with a combination of impressive bat-to-ball skills, quality defense, and athleticism that could appeal to other organizations.

The biggest concern is his health. Conrad was limited to just 36 games this season due to injuries, which have been a bit of a recurring theme throughout his development. Still, the tools are there to make him an interesting trade asset.

Conrad posted an impressive 86.2% overall contact rate with Low-A Myrtle Beach, where he spent most of the season. He also has the ability to drive the ball with authority, thanks in part to a smooth, repeatable swing from the left side. Defensively, he can handle all three outfield positions at a high level. He has the speed to be an asset on the bases, although we didn’t see much of that in 2026, likely due to his injuries.

There really aren’t many glaring weaknesses in Conrad’s game aside from his ability to stay on the field. Assuming he’s healthy this offseason, his tools could make him an appealing buy-low candidate for a team willing to take a chance on his potential. For the Cubs, he could be a valuable piece in a package for a proven big league player. There’s certainly risk in moving a first-round prospect who has yet to get an extended opportunity, but the front office may be able to capitalize on his potential to address a more immediate need.

Jaxon Wiggins, RHP

While Kepley and Conrad could potentially get a deal done themselves (though perhaps more likely alongside another piece), Wiggins would undoubtedly have to be part of a package to bring back a proven major-league asset. He ranks as North Side Baseball’s No. 3 organizational prospect (for now—that ranking will drop in our offseason update) and entered the 2026 season as a top-100 prospect across baseball. The upside is absolutely there for him to become a quality big-league pitcher, but his performance this year raised some questions.

Part of that could be attributed to the elbow inflammation that caused him to miss approximately three months. Still, Wiggins walked 31 batters over 33 1/3 innings with Triple-A Iowa, resulting in a 19.3% walk rate. He was also moved from the rotation to the bullpen. It was a massive step back after his huge breakout in 2025.

Even so, Wiggins has some impressive stuff. His upper-90s fastball can reach triple digits and features truly elite run up in the zone. He also has an upper-80s to low-90s slider that generates plenty of swing-and-miss. The foundation for an impact arm in the majors is easy to see. But that won’t happen if he can’t find the strike zone.

I could see another team taking a chance on Wiggins’ upside, particularly if the Cubs include him alongside another prospect in a deal for established talent. His combination of velocity and swing-and-miss stuff could be enticing for an organization that believes it can help him put everything together.

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