Chicago Cubs Offseason Moves That Already Look Smart, and Dumb

The Chicago Cubs had a big offseason.

Chicago Cubs president of baseball operations Jed Hoyer | Kamil Krzaczynski-Imagn Images

The Chicago Cubs are just a few games into the 2026 season and there is a year's worth of action to evaluate before any sort of dramatic claims can be made.

Without a doubt, though, this was the most headline-filled Cubs offseason in some time with big time moves both in free agency and the trade market. It will be years before we can say for sure which were right and which were wrong, but let's overreact to some of them already.

Here are two moves that already look to have been smart for Chicago and two that look to have been foolish on the part of Jed Hoyer.

Smart: Signing 3B Alex Bregman

Chicago Cubs third baseman Alex Bregman | Matt Marton-Imagn Images

Bregman has not lit the world on fire just yet through four games besides his two home run performance -- a mark that was not hit by the Cubs third base position until the All-Star break last year -- but it looks clear he is exactly what they paid for.

Making an impact both on the field offensively and defensively as well as in the clubhouse, Chicago has taken to Bregman, and Bregman has taken to Chicago. He is going to be a fan favorite for a very long time, and he seems to genuinely be thrilled to be here.

This was a fantastic signing and Bregman should have some very big moments at Wrigley Field.

Dumb: Bringing Back LHP Shota Imanaga

Chicago Cubs pitcher Shota Imanaga | Matt Marton-Imagn Images

Imanaga may take some time to get going, but given the fact he was struggling in the spring, his four runs and six hits allowed over five innings in his season debut is cause for concern. Ultimately, it's just a one-year deal on the qualifying offer, but the Cubs could have gone in a different direction.

Imanaga still is struggling with the long ball and did not look anywhere close to sharp in his debut this past weekend, something which has fans concerned that this year could provide more of the same as the end of last year.

Should the left-hander not be able to get on track, fans are going to question the decision to bring him back all season long.

Smart: Trading for RHP Edward Cabrera

Chicago Cubs pitcher Edward Cabrera | Patrick Gorski-Imagn Images

Following an up-and-down weekend for Chicago pitching, Cabrera came in on Monday night and did exactly what he was brought in to do: generate a ton of swing and miss. The right-hander carved up the Los Angeles Angels lineup with six scoreless innings, striking out five and walking one while allowing just one hit.

Cabrera may just wind up as the ace of this staff, and if he keeps looking how he did on Monday night, he very well could be an All-Star as well.

He still has a ton to prove, but it was as strong a beginning to his time with the team as one could possibly hope for.

Dumb: Trading Away OF Owen Caissie

Miami Marlins right fielder Owen Caissie | Sam Navarro-Imagn Images

Acknowledging the obvious, if Cabrera keeps pitching the way he did in his debut, it won't matter who the Cubs traded to get him. With that being said, the way Chicago's former top prospect has started with the Miami Marlins, it makes fans wish Hoyer had found a way to get Cabrera without sacrificing Caissie.

The 23-year-old has slashed .385/.429/.769 so far this year coming off a huge showing in the World Baseball Classic and even hit a walk-off home run for Miami the other night. The Cubs needed pitching, but seeing Caissie have a huge rookie season would be a tough pill to swallow.

He will be compared against Cabrera in Chicago for the rest of each's respective careers.