Before Sunday’s first pitch, Pete Crow-Armstrong wasn’t just another rising star loosening up on the field — he was busy behind the scenes, helping with Sarah Langs’ game notes. It was a small moment, easy to miss, but it said everything about the culture the Cubs are building: young players buying in, leadership sprouting everywhere, belief bubbling just beneath the surface. From the outside, everything looks golden. The Cubs sit atop the NL Central, the offense hums, and the rotation has been better than advertised. But don’t be fooled — beneath that shiny exterior, major cracks threaten to break open when the pressure rises.
For a franchise hungry to shake off a few years of mediocrity, 2025 already feels different. But an ESPN insider, Buster Olney, refuses to ignore those cracks. During the latest edition of his Baseball Tonight with Buster Olney podcast, he bluntly put it: “There are a lot of great parts with this team. You can see this team playing in a deep October, but there are several things that they have to fix. Third base, rotation, and bullpen,” they all need work.
And the problems aren’t minor.
At third base, the Cubs are dangerously thin on experience. Sunday’s extra-innings stumble only reinforced what scouts and analysts have whispered all spring: you can’t fake playoff poise. Cubs fans might want to believe it’ll just work itself out, but history says otherwise. The hot corner could easily become a fatal weakness when the games start, meaning even more pressure.
Then there’s the bullpen — or more specifically, the alarming number of walks it keeps handing out. Even Julian Merryweather, one of the steadier arms this season, wobbled badly in key moments over the weekend. The Cubs’ internal explanation? “A lot of teams are having bullpen issues — it’s not just us.”
Maybe that’s true. Maybe. But it feels like a dangerous game to play when October demands bullpens that shut the door, not open it wider. Even Dansby Swanson, usually a rock, is batting under .180. While most believe he’ll eventually heat up, the bigger, quieter question is starting to creep in: How long will Craig Counsell wait before making a tough call?
This isn’t a panic button situation — yet. The Cubs have the talent, the swagger, and the chemistry. But the postseason doesn’t hand out trophies for potential. It rewards teams that spot their flaws early and fix them before it’s too late. Right now, the Cubs are being given a warning shot. The real test? What they do next.
Why the Cubs are playing it safe with spending
It’s easy to look at the Cubs, a franchise valued at $4.5 billion and owner of one of MLB’s most recognizable brands, and wonder why they’re not flexing their financial muscle like the Dodgers or Yankees. But peel back the layers, and you’ll find a front office walking a delicate tightrope. After peaking with a top-5 payroll in their 2016 championship window, ownership has since shifted strategy.
Instead of chasing every free agent splash, Tom Ricketts and Crane Kenney have leaned into a long-game approach: aiming for sustained playoff contention rather than one-and-done title shots. According to multiple reports, a key driver is their internal budget mandates — ownership sets parameters that prioritize profitability and maintaining financial flexibility for future core-building years.
Another factor? The rising costs of the National League’s arms race. With the Dodgers handing out nearly $1.2 billion this offseason and the Mets still paying the price for Steve Cohen’s previous spending sprees, the Cubs view measured investments as a safer path. Instead of locking up aging stars to long-term, risky contracts, they’ve chosen targeted moves like trading for Kyle Tucker while trusting younger, cheaper players like Crow-Armstrong and Michael Busch to develop.
The philosophy may frustrate fans craving a splashier roster, but executives believe it gives Chicago a bigger window of opportunity, even if the margins for error, especially in October, are painfully thin.
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