The Cubs’ season ended the way too many of their important seasons have lately: quietly, abruptly, and with more questions than answers.
After another unceremonious Wild Card exit, the real issue isn’t just that Chicago is out. It’s that the organization has spent heavily, talked big, and still doesn’t have a clean explanation for why this keeps happening. Jed Hoyer, Carter Hawkins and Craig Counsell are the people most directly in the spotlight, and Tom Ricketts belongs in the conversation too, even if he already approved nearly $250 million in spending this past season.
That kind of investment is supposed to buy clarity. Instead, the Cubs are more than halfway through Counsell’s five-year contract and still searching for a payoff.
Yes, he’s guided them to the postseason in each of the last two years. But both trips have ended with the same feeling: a team that got to October looking worn down.
2026 was supposed to be the season when everything clicked. The Cubs were supposed to be the club asking, “if not now, when?” Instead, they finished 14 games behind the Milwaukee Brewers in the National League Central, scraped into the playoffs with an 11-13 record in September, and left little reason to believe the script changes in 2027.
That leaves the front office with some uncomfortable places to start.
One of the biggest is whether this core still has enough runway left. It’s a strange question for a team that has reached the playoffs in back-to-back seasons, especially with Pete Crow-Armstrong and Nico Hoerner locked up on extensions at the start of the year. But the results are the results, and after two straight seasons ending the same way, it’s fair to wonder whether the window is already starting to narrow.
That question gets sharper when you look at the money tied up in Hoerner, Alex Bregman and Dansby Swanson. At the same time, there may be room for change this winter.
The Cubs could lose Carson Kelly, Seiya Suzuki and Ian Happ, which could create a chance to bring in fresh pieces and reshape the group. Even if the window isn’t closed, the current core no longer looks like the team’s defining strength.
The pitching injuries are another mess the Cubs have to sort through.
Injuries are part of the sport, and pitching injuries have become a league-wide reality. But for Chicago, this season felt like a case where too many things kept breaking in the wrong direction.
That’s why the Cubs need to ask whether something in their training program contributed to the problem, or whether this was just a brutal stretch of bad luck. They can’t afford to shrug and move on without checking the mirror first.
Then there’s the way the Cubs evaluate pitching additions, which has to be under the microscope after this year.
There’s a pattern here that doesn’t look great. The Cubs have been willing to pay a steep price for unfinished arms, like the trade for Edward Cabrera.
At the same time, they’ve also made bets on expected value in the form of money, only for the process to look shaky once the season starts. Phil Maton was open all offseason about a knee issue, and it never got right during the regular season, yet the Cubs still felt good enough to hand him a two-year deal.
That raises the bigger question: are the Cubs betting on the wrong kinds of pitchers? Maybe the answer is fewer gambles and more commitment to proven results at the top of the market. There’s risk there too, but the upside is a lot more appealing than what Chicago has gotten lately.
And finally, the Cubs have to decide how much they want their identity to depend on run prevention.
For years, that’s been the plan. Build the best defense possible, keep runs off the board, and trust the formula.
The Cubs have indeed had the best defense in baseball. But the last two seasons have shown that defense alone can’t be the main engine for playoff success.
This isn’t because the offense has been bad across the board. It hasn’t.
The problem is more specific: outside of run prevention, the Cubs live and die with the long ball. When the home runs stop coming at a steady pace, the offense can disappear in a hurry.
Defense still matters. It always will. But if the Cubs want a different outcome, it can’t be the centerpiece of everything they do.
In Other News...
Cubs May Regret How Much Jed Hoyer Paid For A Short-Term Push
The Cubs pushed hard at the deadline, and the cost of that urgency is already easy to see in the shape of the deal Jed Hoyer made. Chicago brought in Kevin Gausman and Ryan Zeferjahn to bolster the pitching staff, parting with a batch of prospects that included Brett Bateman, Ty Southisene, Moises Ballesteros and Mason McGwire in the process. It was the kind of move that can look bold in July and much tougher to judge once the season has had time to breathe.
Gausman gave the Cubs nine starts and finished with a 4.83 ERA before getting hurt late in the year, while Zeferjahn showed enough to keep some intrigue with a 4.50 ERA over 18 innings. The harder part for Chicago is looking back at what went out the door: Bateman has performed well with the Blue Jays, while Ballesteros has struggled since landing with the Angels. Those mixed returns only sharpen the question of whether the Cubs paid too much for a short-term push. [Read more 🡒]
Craig Counsell Is Safe But Cubs Changes May Be Coming Behind Him
Craig Counsells first three seasons in Chicago have been productive enough to keep the Cubs in the postseason mix, but not quite enough to quiet the larger questions around a club that expected more. The manager is still viewed as secure in his seat, even as the organization looks ahead to what comes next under a new front office regime.
Ryan Flahertys name is one to watch in that process, with the bench coach potentially in line for managerial chances elsewhere. Tommy Hottovys status is another point of interest, since the Cubs are also weighing ways to sharpen pitching development, and any staff turnover behind Counsell could become one of the first signs of how aggressively the club plans to adjust around him. [Read more 🡒]
Cubs Have A Bigger Offseason Problem Than Losing Two Fan Favorites
The offseason conversation around the Cubs is already drifting toward the usual end-of-year exits, with Seiya Suzuki and Ian Happ expected to hit free agency. Those departures would sting, especially for a club that has leaned on both in recent seasons, but Chicago has at least built enough depth in the outfield to absorb that kind of hit better than it could in other areas.
The bigger issue is on the mound, where ESPNs Jesse Rogers reports the Cubs are expected to make rebuilding the pitching staff their top priority. With several pitchers also set to reach free agency, the club faces work in both the starting rotation and the bullpen, and that is the part of the roster that could shape how quickly Chicago gets back into contention. [Read more 🡒]