\n\tFollowing 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.\n<\/p>\n
\n\tThe 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.\n<\/p>\n
\n\tAll prospect rankings courtesy of North Side Baseball<\/a>.\n<\/p>\n \tKane Kepley<\/a>, OF<\/p>\n \n\tKepley ranks as the Cubs\u2019 No. 5 prospect, and I think his higher floor would make him an attractive target for other teams looking to add young talent.\n<\/p>\n \n\tAcross 125 games between High-A and Double-A this season, Kepley posted a .422 on-base percentage and an .823 OPS.\u00a0He 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\u2019s going to run. He stole 70 bases this season, adding another valuable tool to his profile.\n<\/p>\n \n\tKepley also projects as a strong defender at the major-league level, giving him several ways to contribute even if he doesn\u2019t have 25-homer upside laden in his bat.\n<\/p>\n \n\tI\u2019m 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.\n<\/p>\n \tEthan Conrad<\/a>, OF<\/p>\n \n\tSticking with the young outfielders, Conrad ranks just behind Kepley as the organization\u2019s 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.\n<\/p>\n \n\tThe 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.\n<\/p>\n \n\tConrad 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\u2019t see much of that in 2026, likely due to his injuries.\n<\/p>\n \n\tThere really aren\u2019t many glaring weaknesses in Conrad\u2019s game aside from his ability to stay on the field. Assuming he\u2019s 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\u2019s 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.\n<\/p>\n