Cubs Offseason Shakeup Sparks Burning Questions Fans Can't Ignore

As spring training kicks off, the Cubs bold offseason moves raise key questions about roster strategy, contract negotiations, and their path to contention.

Cubs Report Early to Spring Training with Big Expectations and Bigger Questions

Most of the Chicago Cubs roster has already trickled into spring training - days ahead of the team’s first official workout. That kind of early arrival speaks volumes.

There’s a buzz around this group, and it’s not just about the sunshine in Arizona. After an offseason where the Cubs finally acted like the big-market team they are, expectations are back in Wrigleyville.

Signing Alex Bregman and trading for Edward Cabrera weren’t just headline moves - they were declarations. The Cubs are in win-now mode.

With the core of the Opening Day roster essentially locked in, manager Craig Counsell isn’t wasting time. He’s already named Daniel Palencia the closer, giving the bullpen some early clarity. But make no mistake - this team still has some key questions to answer before the games start to count.

1. How Quickly Will Alex Bregman's Presence Be Felt?

The Bregman signing wasn’t just about filling a hole at third base - though let’s be honest, the Cubs haven’t had a true anchor at the hot corner since Kris Bryant. Bregman brings stability, power, and postseason pedigree to a lineup that’s been searching for a true middle-of-the-order presence. But what’s already turning heads is the way he’s stepping into a leadership role behind the scenes.

According to reports, Bregman’s already been active in helping teammates sharpen their game. Whether it’s pointing out a mechanical tell in Hoby Milner’s delivery or working through adjustments with Pete Crow-Armstrong, Bregman isn’t waiting for Opening Day to make his presence known. He’s doing what great veterans do - making the team better from day one.

2. Can the Nico Hoerner Trade Rumors Be Put to Bed?

The trade chatter around Nico Hoerner didn’t start with the Bregman signing, but it certainly got louder after it. With the Red Sox reportedly backing away from talks, it seemed like the noise might finally die down. But unless Hoerner puts pen to paper on a contract extension before Opening Day, those rumors are going to keep simmering.

The Cubs aren’t in the business of making panic moves, but they’re also not shy about listening. If the team falters by midseason, or if Matt Shaw shows he’s ready for an everyday role, Hoerner could find himself back in the trade conversation. He’s a valuable piece - both on the field and in the clubhouse - but value cuts both ways when the trade deadline approaches.

3. Will the Cubs Lock in Any Contract Extensions?

Hoerner isn’t the only Cub with an uncertain future. Ian Happ, Seiya Suzuki, Carson Kelly, Matthew Boyd, Jameson Taillon, and Shota Imanaga are all set to hit free agency next offseason. And with a relatively thin free-agent class on the horizon, there’s a real chance several of those names could test the open market.

Still, the most intriguing extension candidate might not be a pending free agent at all. Pete Crow-Armstrong remains a long-term priority for this front office.

Talks reportedly didn’t go anywhere last year, but the relationship between player and team remains strong. There’s no immediate pressure - PCA still has time before free agency looms - but locking him in now could be a savvy move for a club trying to build something sustainable.

4. Are the Cubs Done Making Moves?

The Cubs came into spring training with most of the heavy lifting done. Bregman and Cabrera were the big swings, and they landed both.

That gives the front office some flexibility - they don’t need to chase every name still out there. But that doesn’t mean they’re done.

Zac Gallen remains unsigned, and while a deal might not be likely, the Cubs have a history of pouncing on late-offseason opportunities. A veteran fourth outfielder could also be on the radar if the right fit emerges. The bottom line: this roster is close to set, but don’t count out a final tweak or two before Opening Day.


The Cubs are entering 2026 with a clear message: the rebuild is over. This is a team built to compete now.

With a mix of veteran leadership, young talent, and a front office finally willing to spend like a contender, the pieces are in place. Now comes the hard part - putting it all together on the field.