The Kris Bryant trade has come full circle and it’s a stark reminder of how badly it turned out for the Chicago Cubs.
Earlier in the offseason former top Cubs pitching prospect Caleb Kilian became a free agent after missing most of the 2025 season with an injury and now the 28-year-old pitcher is headed back to the San Francisco Giants.
Jed Hoyer was the architect of the Cubs’ rebuild beginning in 2021, which was much maligned by fans as the team traded away most of its World Series core at the trade deadline. That included the 2016 National League MVP, as Bryant was dealt to the Giants for Kilian and outfielder Alexander Canario.
Now, as we look forward to the 2026 season, we can finally close the book on the trade that turned out to be a dud for the Cubs.
Kilian pitched in eight total games across three seasons with the Cubs and ended his time with the club by posting a 9.22 ERA in 27.1 innings. The last few years Kilian barely hung onto a 40-man roster spot before he was ultimately designated for assignment and brought back on a minor league deal in 2025, only to see the right-hander sidelined for four months.
The Cubs moved Kilian to a full-time reliever role at Triple-A, but he was never seen as an option for the MLB bullpen in 2025. Now, he’ll try to recapture whatever he has left with the Giants, who drafted him back in 2019.
As for Canario, he spent the 2025 season with the Pittsburgh Pirates after he was traded by the Cubs to the New York Mets in spring training and was eventually DFA’d prior to Opening Day. The right-handed hitting outfielder had six home runs in 87 games with the Pirates and slashed .218/.274/.338, posting a 68 wRC+ in 234 plate appearances.
The Cubs didn’t have much space in the outfield for Canario and he was only given 21 games with the team in 2023-24.
Canario has now signed with the Seibu Lions of the NPB in Japan.
(Previous Update)
Well, it looks like Caleb Kilian’s time with the Chicago Cubs has now come to an end. The former top pitching prospect, who was part of the Kris Bryant trade in 2021, is now a free agent heading into the 2026 season. The 28-year-old missed most of the 2025 season with an injury and was limited to only 15.2 innings.
It’s certainly a disappointing end to his tenure that was already prompted with a DFA earlier in the year. Kilian made a total of eight appearances in the big leagues with the Cubs from 2022-24, and the right-hander unfortunately was never able to get any positive momentum. Kilian posted a 9.22 ERA in 27.1 innings with 21 strikeouts, 20 walks and a 0-4 record.
Other notable Cubs minor leaguers who became free agents this past week alongside Kilian include Pablo Aliendo and Chase Strumpf.
So, that puts a bow on the Bryant trade as Alexander Canario was let go back in spring training and eventually ended up with the Pittsburgh Pirates. Kilian pitched in eight games for the Cubs, while Canario played in 21 games with the Cubs.
Caleb Kilian’s Cubs Career
Kilian came over from the San Francisco Giants without much hype. He was their No. 30 ranked prospect according to MLB Pipeline, but there was hope the Cubs could make him better. And well at first things looked promising for the right-handed starting pitcher.
Kilian began the 2022 season with the Iowa Cubs at Triple-A. He recorded a 2.06 ERA in nine starts, leading up to his MLB debut against the St. Louis Cardinals on June 4, 2022. A few days before his first big-league game, Kilian was ranked in Baseball America’s top-100 prospects list.
His debut could not have gotten off to a better start. Nine up and nine down, as Kilian was perfect through three innings at Wrigley Field. He did get into trouble in the fourth inning, giving up three earned runs, but overall a decent MLB debut for the righty, who pitched five innings against the Cardinals.
Then, things went downhill fast. Kilian was optioned back to Triple-A and then brought back up to the majors for two more starts later in June. He walked 10 batters, allowed 8 hits and was charged with 10 earned runs in 6.1 combined innings against the San Diego Padres and Pittsburgh Pirates, respectively.
All of a sudden Kilian lost the ability to find the strike zone. In his first nine starts at Triple-A in 2022, he had a 9.1 BB%. After his MLB debut against the Cardinals Kilian made 17 more starts at Triple-A and his walk rate spiked to 14.1%.
In 2023, Kilian got another shot with the Cubs, who needed an emergency starter against the Miami Marlins in late April. He didn’t have major issues with walks this time around, but Kilian was knocked around hard to the tune of seven earned runs on 10 hits in 3.1 innings. He spent most of the year in the minors and only made two more appearances for the Cubs, a pair of one-inning relief outings in August.
There was a bit of hope that Kilian had turned the corner during spring training in 2024. He was lighting up the radar gun in Arizona, but then a shoulder strain landed Kilian on the 60-day injured list prior to Opening Day. Kilian came back in July, pitched well as a starter and reliever in Triple-A, and then made two starts with the Cubs in September.
On Sept. 29, 2024, Kilian pitched in his eighth career game with the Cubs. It was the best outing in his abbreviated MLB career, throwing five shutout innings against the Cincinnati Reds.
Now, Kilian will have to earn his way on the 40-man roster if he ever wants another opportunity in the majors with the Cubs.
