Cubs Take a Step Forward in 2025-But Will They Take the Leap in 2026?

As the dust settles on the 2025 season, the Chicago Cubs find themselves in a familiar spot-competitive, promising, but not quite over the hump. Their year ended with a thud in the NLDS, bowing out in Game 5, but let’s not overlook the progress.

For the first time since 2018, the Cubs cracked the 90-win mark, and they returned to the postseason for the first time since 2020. That’s not nothing.

They even gave fans a taste of October drama, knocking off the San Diego Padres in the Wild Card Series. Sure, the bats went cold against a relentless Padres bullpen, but the series win was a milestone for a club that’s been grinding through a rebuild and trying to find its footing in a competitive National League.

Now, with the offseason in full swing, the Cubs are in roster-building mode. So far, the moves have been more about depth than sizzle.

They’ve brought back left-hander Shota Imanaga on the qualifying offer and re-signed veteran reliever Caleb Thielbar to a one-year deal. In free agency, they’ve added Tyler Austin, Phil Maton, Hunter Harvey, Jacob Webb, and Hoby Milner.

Solid pieces? Absolutely.

Game-changers? Not quite.

That’s the tension hanging over this offseason. The Cubs are clearly in the mix and have the bones of a team that can contend, but they haven’t made the kind of splash that signals they’re going all-in. That’s why, in a year-end grading of NL Central teams, Chicago landed a “B” for 2025-a respectable mark, but one that reflects both progress and missed opportunity.

Among their division rivals, that grade put the Cubs in the middle of the pack. The Cardinals and Pirates struggled through tough seasons and earned grades to match (D+ and C-, respectively). The Brewers, meanwhile, came away with the top mark-an A–after winning the division and making a run to the NLCS.

The one ranking that might raise some eyebrows? The Cincinnati Reds getting a B+.

They finished behind the Cubs in the standings and got swept out of the Wild Card Series. And like the Cubs, they’ve been quiet this winter.

So why the edge? That’s up for debate.

But when your most notable offseason move is signing Phil Maton to a multi-year deal-the only one the Cubs have handed out so far-it’s hard to argue too loudly about report card semantics.

The good news? There’s still plenty of offseason left, and the Cubs aren’t done.

They’ve been linked to several top-tier free agents, including Alex Bregman. They missed out on Japanese right-hander Tatsuya Imai, which only adds pressure to land a big fish.

With Kyle Tucker’s likely departure looming, the front office has both the need and the opportunity to make a major move.

What’s clear is this: 2025 marked a real step forward. After years of retooling, the Cubs look like a team ready to contend again.

But turning that step into a leap-into a team that doesn’t just make the playoffs, but makes noise when they get there-will require more than incremental upgrades. The foundation is there.

Now it’s about building the rest of the house.

The North Side is hungry for October baseball that lasts. The Cubs have the chance to deliver it in 2026. The question is: will they go out and seize it?