End of an Era: Caleb Kilian’s Emotional Cubs Exit Closes the Book on the Kris Bryant Trade.vc
End of an Era: Caleb Kilian’s Emotional Cubs Exit Closes the Book on the Kris Bryant Trade
The once-promising chapter of the Chicago Cubs’ rebuild, inaugurated by the trade of franchise icon Kris Bryant in 2021, has officially closed. Pitcher Caleb Kilian, who was a centerpiece of that return package, has elected free agency, marking an emotional final departure from the organization.
The sentiment “I’ll miss everyone so much…” captures the painful end to a tenure that began with high expectations but was ultimately derailed by struggles and injuries.
The Origin: The Kris Bryant Trade
Kilian, a right-handed pitcher, was acquired by the Cubs from the San Francisco Giants on July 30, 2021, along with outfielder Alexander Canario, in exchange for the former MVP Kris Bryant.
- Initial Promise: At the time of the trade, Kilian was lauded as one of the top pitching prospects in the Giants’ system and was seen as a future anchor for the Cubs’ rotation. He capped his first minor league season in the Cubs system by winning the Arizona Fall League Championship Game MVP Award after throwing six perfect innings.
- The Struggle: Kilian made his MLB debut in June 2022 but struggled mightily with control and consistency. Across parts of three seasons (2022–2024), he posted a combined 9.22 ERA and a 2.01 WHIP in 27.1 major league innings.
- Final Chapter: His struggle was complicated by a teres major shoulder strain that sidelined him for most of 2024. After a disastrous first start in Triple-A in 2025, the Cubs designated him for assignment in April. Though he was briefly re-signed to a minor league deal, he elected free agency on November 6, 2025.
The Trade’s Final Score
With Kilian’s departure, the Cubs have officially closed the book on the return package for Kris Bryant:
- Caleb Kilian: Now a free agent.
- Alexander Canario: Was designated for assignment in Spring Training 2025 and subsequently traded out of the organization (now with the Pittsburgh Pirates).
As one report noted, the trade for Bryant, who left the Giants in free agency that winter, “aged horribly for the Cubs,” as they received virtually no meaningful MLB production from the prospects acquired.
Kilian’s Future
Kilian, 28, now enters the open market. His minor league numbers—a 4.37 ERA over parts of four Triple-A seasons—and his past prospect pedigree suggest he is likely to sign a minor league contract with a non-roster invitation to Major League Spring Training with another organization, hoping a fresh start can unlock his once-elite control.
The Cubs are now looking to strengthen their minor league pitching depth after losing several experienced arms, including Kilian. Would you like to know the most appealing minor league free agent pitchers who could fit the Cubs’ pitching development needs this offseason?
The once-promising chapter of the Chicago Cubs’ rebuild, inaugurated by the trade of franchise icon Kris Bryant in 2021, has officially closed. Pitcher Caleb Kilian, who was a centerpiece of that return package, has elected free agency, marking an emotional final departure from the organization.
The sentiment “I’ll miss everyone so much…” captures the painful end to a tenure that began with high expectations but was ultimately derailed by struggles and injuries.
The Origin: The Kris Bryant Trade
Kilian, a right-handed pitcher, was acquired by the Cubs from the San Francisco Giants on July 30, 2021, along with outfielder Alexander Canario, in exchange for the former MVP Kris Bryant.
- Initial Promise: At the time of the trade, Kilian was lauded as one of the top pitching prospects in the Giants’ system and was seen as a future anchor for the Cubs’ rotation. He capped his first minor league season in the Cubs system by winning the Arizona Fall League Championship Game MVP Award after throwing six perfect innings.
- The Struggle: Kilian made his MLB debut in June 2022 but struggled mightily with control and consistency. Across parts of three seasons (2022–2024), he posted a combined 9.22 ERA and a 2.01 WHIP in 27.1 major league innings.
- Final Chapter: His struggle was complicated by a teres major shoulder strain that sidelined him for most of 2024. After a disastrous first start in Triple-A in 2025, the Cubs designated him for assignment in April. Though he was briefly re-signed to a minor league deal, he elected free agency on November 6, 2025.
The Trade’s Final Score
With Kilian’s departure, the Cubs have officially closed the book on the return package for Kris Bryant:
- Caleb Kilian: Now a free agent.
- Alexander Canario: Was designated for assignment in Spring Training 2025 and subsequently traded out of the organization (now with the Pittsburgh Pirates).
As one report noted, the trade for Bryant, who left the Giants in free agency that winter, “aged horribly for the Cubs,” as they received virtually no meaningful MLB production from the prospects acquired.
Kilian’s Future
Kilian, 28, now enters the open market. His minor league numbers—a 4.37 ERA over parts of four Triple-A seasons—and his past prospect pedigree suggest he is likely to sign a minor league contract with a non-roster invitation to Major League Spring Training with another organization, hoping a fresh start can unlock his once-elite control.
The Cubs are now looking to strengthen their minor league pitching depth after losing several experienced arms, including Kilian. Would you like to know the most appealing minor league free agent pitchers who could fit the Cubs’ pitching development needs this offseason?
