Cubs Offseason Hype Means Nothing Without Multiple Big Moves

The latest discourse surrounding the Chicago Cubs and the upcoming offseason has the team making “a splash move” or two in free agency.

ESPN's Buster Olney labeled the Cubs as one team the industry believes is going to swing big, highlighting Chicago's veteran hitters that place them in win-now mode.

It's about time the starting pitching matched that prolific offense, which scored the most runs in baseball during the 2026 season.

The current Cubs starting rotation is nowhere near ready. Matthew Boyd and Clay Holmes both declined their options and chose to become free agents, leaving the current rotation consisting of Ben Brown, Justin Steele, Edward Cabrera, Javier Assad, and Braxton Garrett.

There is no doubt the Cubs will be active, but a splash? What exactly does that mean? I think that's an important distinction as we head into an offseason that could see the Cubs be one of the more active teams in baseball.

We've seen the Cubs address their starting pitching in the offseason before. Last winter, Chicago brought back Shota Imanaga on the qualifying offer, then swung a trade for right-handed pitcher Edward Cabrera by dealing top prospect Owen Caissie to the Miami Marlins.

At the trade deadline, the Cubs moved top prospects for right-handed pitcher Clay Holmes from the New York Mets and right-handed pitcher Kevin Gausman from the Toronto Blue Jays. None of it was good enough come playoff time. Cabrera didn't even make it to the end of the regular season in the starting rotation.

So I think it's important that we don't confuse action with meaningful action. We shouldn't consider sheer activity to be a splash. For the Cubs to make waves, like they need to this winter, they need to swing at the top of the market. And they probably need more than one big fish.

That means spending in free agency rather than resorting to the trade market. That means running up the payroll in a way that matches the revenue of the Chicago Cubs and puts them in the same tier as the top teams in the sport.

If recent reports are to be believed, they seem prepared to do that.

According to ESPN's Jeff Passan in a recent write-up, “the Chicago Cubs badly want Tarik Skubal.” And signing Skubal would certainly be a splash, but it may not be big enough.

When I look at the top five starting pitchers on the market, the Cubs need to land two of them to make a meaningful splash and have the hype surrounding their offseason be justified. Michael King by himself is a good signing, but it's no different than the singular additions Chicago has made to its rotation in the past. The same goes for Freddy Peralta. Add both of them, and the Cubs are the talk of the offseason.

Add Skubal, then swing a trade for another prized arm, like Reid Detmers from the Los Angeles Angels, and the Cubs will have completely restored their starting rotation.

But we've seen this song and dance from Jed Hoyer and the Cubs front office before. We've seen Chicago try to preserve spots in the rotation for pitchers who are unreliable. I believe in Justin Steele as much as the next person, but did the Cubs not learn a lesson in 2026 that Steele can no longer be penciled into the rotation?

Anything he gives Chicago moving forward should be treated as house money. The same thing goes for Ben Brown, who has yet to throw more than 106.1 innings in a single season in his career.

Perhaps Buster Olney is right. Perhaps the Cubs will make a splash this offseason. But that doesn't mean making one move and landing a top free agent. It means taking multiple swings, making multiple additions to the starting rotation, and leaving little room for doubt that the Chicago Cubs are one of the very best teams in Major League Baseball.