The Kris Bryant Trade Comes Full Circle – And It’s a Tough Pill for Cubs Fans

When the Chicago Cubs traded Kris Bryant to the San Francisco Giants back in 2021, it marked the end of an era – and the beginning of a rebuild that’s still trying to find its footing. Now, as we head into the 2026 season, the final threads of that deal have unraveled, and it’s clear: the Bryant trade didn’t pan out the way the Cubs had hoped.

The last remaining piece from that deal, right-hander Caleb Kilian, is heading back to where it all started. After missing most of 2025 with an injury, the 28-year-old pitcher signed a minor league deal with the Giants – the same team that drafted him in the eighth round back in 2019. It’s a full-circle moment, but not the kind Cubs fans were hoping for when they said goodbye to their 2016 MVP.

A Trade That Never Took Off

At the time of the trade, the Cubs received Kilian and outfielder Alexander Canario in exchange for Bryant, who was in the final year of his contract. The move was part of a broader teardown led by team president Jed Hoyer, who was reshaping the roster and stockpiling young talent. But in hindsight, the return didn’t deliver the kind of impact that justifies trading a franchise cornerstone.

Kilian’s time in Chicago was marked by flashes of potential, but ultimately defined by inconsistency and injury. Over three seasons, he made just eight appearances in the big leagues and posted a 9.22 ERA in 27.1 innings.

The Cubs tried to find a role for him – moving him to the bullpen in Triple-A, giving him spot starts, even bringing him back on a minor league deal in 2025 – but nothing stuck. A shoulder injury sidelined him for four months last year, and by season’s end, he wasn’t even in the conversation for a major league bullpen spot.

Now, he’s back with the Giants, hoping to rediscover the form that once made him a top-30 prospect in their system.

Canario’s Brief Window

Alexander Canario’s path wasn’t much smoother. After a short stint with the Cubs – just 21 games across the 2023 and 2024 seasons – he was traded to the Mets during spring training in 2025. The Mets quickly designated him for assignment, and he landed with the Pittsburgh Pirates.

In Pittsburgh, Canario got more playing time, but the results were underwhelming. In 87 games, he hit six home runs and slashed .218/.274/.338, with a 68 wRC+ over 234 plate appearances.

That’s well below league average, and it wasn’t enough to keep him in the big leagues. He’s now signed with the Seibu Lions in Japan’s NPB, looking for a fresh start overseas.

The Rise and Fall of Caleb Kilian

Kilian’s story is one of early promise that faded fast. When he arrived in the Cubs system, there was optimism that the organization could help him take the next step. And early on, it looked like they might be onto something.

In 2022, Kilian opened the season in Triple-A Iowa and impressed with a 2.06 ERA over nine starts. That earned him a call-up to the majors, where he debuted against the St.

Louis Cardinals on June 4. His first three innings were spotless – nine up, nine down – and it looked like the Cubs had found a gem.

But the fourth inning unraveled, and while he managed to finish five innings, the outing was a preview of the inconsistency that would follow.

Kilian was sent back to Triple-A, but returned for two more starts later that month. Control issues plagued him – 10 walks in 6.1 innings – and he gave up 10 earned runs in outings against the Padres and Pirates. His walk rate ballooned in the minors, jumping from 9.1% before his debut to 14.1% over his next 17 Triple-A starts.

In 2023, he got another shot with the big league club in April, stepping in as an emergency starter against the Marlins. This time, it wasn’t the walks – it was the contact.

Kilian gave up 10 hits and seven earned runs in just 3.1 innings. He spent most of the year in the minors, making only two more brief appearances in the majors as a reliever.

There was a glimmer of hope in spring training 2024. Kilian was throwing with more velocity and looked sharp in Arizona.

But a shoulder strain derailed his season before it started, landing him on the 60-day IL. He returned in July and pitched well in Triple-A, both as a starter and reliever, before getting two more starts with the Cubs in September.

His final outing – five shutout innings against the Reds on Sept. 29, 2024 – was easily the best of his career. But it wasn’t enough to secure his spot. He was removed from the 40-man roster and became a free agent at season’s end.

Closing the Book

With Kilian now back in San Francisco and Canario off to Japan, the Kris Bryant trade is officially in the books – and it’s hard to call it anything but a miss for the Cubs. Neither player made a significant impact at the major league level, and both have moved on without establishing themselves in Chicago.

It’s a reminder of how difficult it is to win trades involving star players, especially when those players are still producing. Bryant may not be the MVP-level force he once was, but the Cubs never got close to replacing his value with the return they received.

As the Cubs continue to build toward their next competitive window, the Bryant trade stands as a cautionary tale – not just about talent evaluation, but about the unpredictable nature of player development. Sometimes, even the most promising prospects don’t pan out. And sometimes, the cost of moving on from a franchise icon lingers longer than expected.