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Caleb Kilian is once again leaving the Chicago Cubs' organization. The top pitching prospect acquired by the Cubs in the Kris Bryant trade at the 2021 MLB trade deadline was previously designated for assignment by the Cubs but stuck around in the organization after he was outrighted from the 40-man roster. Kilian was among a handful of Cubs' minor leaguers to declare for free agency this offseason.
26 Cubs minor leaguers became free agents today. Among the most recognizable names on the prospect front:
— Greg Huss (@OutOfTheVines) November 7, 2025
Pablo Aliendo
Ethan Hearn
Corey Joyce
Caleb Kilian
Rafael Morel
Miguel Pabon
Antonio Santos
Chase Strumpf
Mitchell Tyranski
When Kilian made his Major League debut for the Cubs in 2022, there was excitement as his arrival signaled hope for what could be next for the North Siders. A season removed from the World Series' core being torn down, Kilian's debut had the impression of the organization ready to turn the corner to their next contention window. While the Cubs have been a contender in each season since 2023, Kilian has had virtually nothing to do with their success.
In 8 career appearances with the Cubs at the Major League level, Kilian is holding onto an ERA of 9.22 with a career walk rate of 14.6%. Injuries thwarted any path back to the majors for Kilian after 2022, and he only made 11 appearances at the minor-league level this past season.
The book on the Kris Bryant trade is officially closed for the Chicago Cubs as Caleb Kilian leaves the organization.
It's the final indicator that the Bryant trade aged horribly for the Cubs. No, the Cubs wouldn't have been better off keeping the 2016 National League MVP, considering his back is begging him to retire, but Jed Hoyer's return in the deal speaks to why a revamp was needed of the team's farm system.
The other prospect in the Bryant deal, Alexander Canario, spent the 2025 season with the Pittsburgh Pirates. In 234 plate appearances this season, Canario was far from the power bat the Cubs projected him to be, hitting only 6 home runs with a wRC+ of 68.
The 2021 sell-off suddenly has a very different feel to it. While the Cubs, for the most part, made the right decisions in resetting their core, Pete Crow-Armstrong and Kevin Alcantara are suddenly the only pieces viable from the prospects they got back in the respective trades. Alcantara's prospect shine has worn off over the last year, but he could still be a key trade piece for the Cubs this offseason as they look toward potential trades this offseason.