Was the 2026 Chicago Cubs Season a Success or a Failure?

[Brian Kelder]

Image courtesy of Matt Marton-Imagn Images

For decades, Cubs fans have been conditioned to believe that any appearance in the playoffs constitutes a successful season. I can remember all the playoff teams from my childhood—though, granted, only 1984 and 1989 apply, so it isn't hard. Even the collapse years of 1969, 1973 and 2004 hold fond places in some fans' memories. Any year in which they avoided that kind of embarrassment was automatically a winner.

At long last, this seems to have shifted. The team has made the playoffs seven times since 2015, which is one more trip they booked from 1984 to 2014. Obviously, it's gotten much easier to make the playoffs over that time, but still, the fans now consider reaching the postseason to be a bare minimum—the first criterion of a successful year, but not a final or sufficient one. 

So, was the entire 2026 season a failure? If so, for whom? Was it Craig Counsell's folly? Can Jed Hoyer build a true contender? Is it that cheap billionaire, Tom Ricketts? 

All I know is that it's no longer a success to just get in the playoffs. That should have been clearly true beginning in the late 1990s, but it finally seems to have become true since 2016. Fans expect not only to reach October, but to succeed there. Of course, as the team was forcefully reminded in each of the last two years, there's no simple formula for winning in the playoffs. The only reliable way to do so is to get there a lot, in as strong a seeded position as possible. That they've only gone to the tournament at all in two of the last seven seasons is the biggest problem; that they haven't made it with an intact starting rotation or as a division winner with home-field advantage on their side in the Division Series is the second-biggest.

Jed Hoyer did his best work this year, despite his admission of failure in constructing the bullpen. This was his masterclass, and it wasn't enough. The spending was there, led by a hefty investment in Alex Bregman. He tried to be more proactive about the pen, and he traded for Edwin Cabrera. Three top-100 prospects were moved in attempts to bolster the team for this season. His best effort? Eighty-nine wins, and another distant second-place finish in the NL Central.

The season was both a success and a failure. For the players on the field, there really can be no quibbles. They were a perfectly fine, entertaining team to watch. It didn't take much watching of other games to recognize just how good the Cubs' defense was, and many drops of water have cooled internet servers writing about the incredible season that Pete Crow-Armstrong submitted. They were successful in the roles they were placed in.

The failure is on the front office. They quite simply have not achieved their goals. They spent a lot of money to build this team initially and supplemented it with trade deadline acquisitions. Their spot in the playoffs was never in jeopardy. But even before they arrived in San Diego, it seemed clear they would run out of steam before reaching the World Series. 

Once they were in, they didn't have the ammunition to do anything. Their pitching had no chance of holding up through the Wild Card and two other NL Series, let alone the Fall Classic. With the lowest pitching WAR in baseball, they ran out of quality arms in August.

It's time to ask if Jed Hoyer is the man to run the Cubs. As he admitted Friday in his end-of-year press conference, the organization needs to completely overhaul the way it scouts, acquires and develops pitchers, as well as how it tries to keep them healthy. Meanwhile, they also have to replace three key departing position players and virtually their whole pitching staff—not philosophically, but actually, and quickly, in an offseason that will be complicated by a work stoppage.

It's going to be a huge job for Hoyer to replace everything, and it's fair to question if he should be able to do it. The Cubs are in a tougher situation going forward than most people have realized. Theo Epstein took four years and had a contender; Hoyer has had six and seems to be running out of runway, while still trying to get his team off the ground.

Celebrate the players, but hold the front office's feet to the fire. It's not been what was promised: sustained contention. In fact, that feels a long way off—especially given the way Cubs fans now demand to define that phrase.

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[Arlen]

Rather than hold the front office's feet to the fire, I think I'll step back and see what they do. MLB is a big reality show.

[Rex Buckingham]

They got a singularly brilliant season out of PCA and still barely made the playoffs and feebly exited a round earlier than last year. I would call the season a failure overall, even with lots of incredible moments of brilliance.

[tornmeniscus]

Its a failure.

[GuyA]

They had the third best run differential, had a predicted W/L of 95 wins vs 89W reality. So on some level the total is less than the sum of the parts. That's not success. That's hard to explain especially since it is a virtual repeat of 2025 with 96W predicted 92W reality. Bad manager? Bad GM? Bad luck?  I'm inclined to think it is because they insist on going into the season with an incomplete team and revamping it at the trading deadline for better or worst just because they can. Also very weird choices for playoffs.

[SB in SC]

Organizational failure.  The players played to their abilities.  The on field coaching staff did what they could with what they had.  The philosophy of not valuing velocity or strike outs has failed (Cabrera was an effort to go in the right direction).  The reluctance to pay for a bullpen arm that is elite, due to their "volatility year over year" has been a failure.  More draft picks from later rounds and IFA signings have to contribute to the MLB roster in a meaningful way.  I can't think of the last Cubs draft pick not picked in the 1st round has contributed to the Cubs MLB team for multiple years. 

Jed finally traded some redundant pieces in an effort to compete which is an improvement.  I also like having multi inning relievers like Civale, Rea and Assad to protect the bullpen.  If the Cubs are going to get guys with a thin margin for error they need to be ground ball guys (Peterson) and not fly ball guys.

Maybe the Cubs would be better off if Carter Hawkins gets a promotion away from the Cubs to bring in someone with a different way of looking at things.  They have at least 100 million to spend and 3 starters to replace and a pitching staff to rebuild.  Let's see what happens.

[Soul]

Clearly a failure. Limping in as WC2 and being swept aside with a flick of a finger is objectively below expectations. Sure, injuries played a role. That’s not the question though. The question is about the outcome. 

[Paul7]

On 10/3/2026 at 11:23 AM, GuyA said:

They had the third best run differential, had a predicted W/L of 95 wins vs 89W reality. So on some level the total is less than the sum of the parts. That's not success. That's hard to explain especially since it is a virtual repeat of 2025 with 96W predicted 92W reality. Bad manager? Bad GM? Bad luck?  I'm inclined to think it is because they insist on going into the season with an incomplete team and revamping it at the trading deadline for better or worst just because they can. Also very weird choices for playoffs.

Without a half dozen gruesome ninth inning bullpen crashes they would have been at 95.

[Paul7]

On 10/3/2026 at 12:13 AM, Rex Buckingham said:

They got a singularly brilliant season out of PCA and still barely made the playoffs and feebly exited a round earlier than last year. I would call the season a failure overall, even with lots of incredible moments of brilliance.

Take away PCA and the Cubs are a .500 team.  Our starter in the playoffs would be a #4 starter with a serious WS contender.  The bullpen was a complete joke.  Terrible small ball game, not good at moving runners along or bunting.  Jed has to go.  The question is, do the Cubs see it as a failure?  Attendance was almost 3M, are they just going to live off the 2016 glory like the Bears have with 1985?

Edited Monday at 02:47 PM by Paul7