The right-hander, who was the centerpiece of the 2021 Kris Bryant trade, is now a free agent, marking a disappointing end to a once-promising return.
CHICAGO — The Chicago Cubs are officially parting ways with Caleb Kilian, marking the end of a chapter that once carried significant expectations. Kilian, the right-handed pitcher acquired in the 2021 trade that sent icon Kris Bryant to the San Francisco Giants, is now a free agent after being among 26 Cubs minor leaguers to hit the open market this offseason.
For Cubs fans, Kilian’s name once symbolized hope. When he made his big-league debut in 2022, just a year after the Cubs dismantled their 2016 World Series core, there was genuine optimism that Kilian could be a key piece in the next wave of talent.
His arrival felt like a signal that the rebuild wasn’t just about tearing down. But Kilian never found his footing at the major league level.
In eight career appearances with the Cubs, Kilian posted a 9.22 ERA and struggled mightily with command, walking nearly 15% of the batters he faced. Injuries only made things more difficult, limiting him to just 11 appearances in the minors this past season.
A Failed Return: The Kris Bryant Trade in Hindsight
With Kilian’s departure, the book on the Kris Bryant trade is officially closed—and it’s hard to ignore how little the Cubs ultimately received.
The other player in that trade, outfielder Alexander Canario, spent the 2025 season with the Pittsburgh Pirates after being traded away. In 234 plate appearances, he managed just six home runs and posted a below-average wRC+ of 68, falling short of the power potential the Cubs once envisioned.
In hindsight, the Bryant deal—once viewed as a key piece of the retooling—now looks like a missed opportunity. While Bryant’s own injury history has led to a decline in production, the return package of “upside prospects” failed to materialize on the field for Chicago.
More broadly, the 2021 trade deadline, when the Cubs hit the reset button, has taken on a new tone. Of all the prospects acquired during that sell-off (which also included trades of Anthony Rizzo and Javier Báez), only Pete Crow-Armstrong and Kevin Alcántara remain as meaningful pieces in the organization.
Crow-Armstrong has established himself as a dynamic, Gold Glove-winning center fielder. Alcántara’s prospect stock has dipped but he could still be a valuable trade chip this offseason.
As for Kilian, his time in the Cubs organization ends not with a bang, but with a quiet exit, a reminder of how unpredictable prospect development can be.
