Cubs Could Wind Up Regretting Blockbuster Trade as Former Top Prospect Rakes

Will the Chicago Cubs wind up regretting their choice?

Jed Hoyer | Kamil Krzaczynski-Imagn Images

The Chicago Cubs went into the offseason with the goal of rebuilding their pitching staff, and they did just that when they made arguably the most significant trade of the winter.

Jed Hoyer acquired a potential ace who is young and controllable in Edward Cabrera from the Miami Marlins, but it did not come at a small cost. The Cubs traded away a package headlined by their top prospect in Owen Caissie, who was expected to have an everyday role this season.

Just as was the case last spring with Cam Smith mashing for the Houston Astros in spring following the Kyle Tucker trade, Caissie has been on an absolute tear for Team Canada at the World Baseball Classic.

Caissie giving Cubs second thoughts with WBC performance

Miami Marlins right fielder Owen Caissie | Jim Rassol-Imagn Images

While Caissie was struggling a bit in spring training with the Marlins in a very small sample size, something clicked once he reported to Team Canada as one of their bright young stars who has helped lead them into the quarterfinals.

In four WBC games, Caissie is slashing an absurd .500/.529/.929 with a home run and five RBI, racking up seven total hits in just 14 at-bats.

Owen Caissie in the World Baseball Classic:

14 AB
.500 / 1 HR / 5 RBI
5 K : 2 BB

He is going to get a long leash to prove he can play this season. pic.twitter.com/fJNxX8D2vX

— Andrew DeCeglie (@Andrew_FBB) March 12, 2026

Practically putting the team on his back, Caissie will try to keep it going on Friday night when Canada faces Team USA for the right to advance to the semifinals of the tournament. While it would be a massive upset, Canada, led by Caissie, seems to be on a mission, and the US team must not overlook their neighbors to the north.

Beyond Friday night, though, Caissie looks like someone who could make Chicago think twice about their decision to trade him if Cabrera is not everything they had hoped for.

Will Caissie have a huge season for Miami?

Chicago Cubs right fielder Owen Caissie | Patrick Gorski-Imagn Images

In 2025, the young slugger played in 99 games at Triple-A Iowa and slashed .286/.386/.551 with 22 home runs and 55 RBI while pushing towards the big leagues. Though he survived being dealt by the Cubs at the deadline, ultimately, the prospect of adding Cabrera was too much for Hoyer to pass up.

If Cabrera struggles or gets injured, though, Chicago fans will be watching Caissie's performance very closely to see whether the Cubs made the right call by moving off him before he even got a real chance.

Regardless, what's done is done, and Caissie will have eyes on him from up north for the remainder of his Major League career.