Cubs October Outlook Looks A Lot Worse Than The Standings Suggest

Can the Chicago Cubs overcome a season marred by pitching injuries and underperformance to make a deep postseason run?

The Chicago Cubs have a problem that can’t be hidden by a strong lineup or an MVP-level star. Their pitching has cratered.

Entering Tuesday, Craig Counsell’s club sat fifth in team WAR, powered by an MLB-best 34.5 batting WAR. But the other side of the ledger tells the real story: a league-worst 3.6 pitching WAR. That gap is massive, and it has put the Cubs in real danger of squandering a big season from 24-year-old outfielder Pete Crow-Armstrong, who has piled up 9.9 fWAR, along with a resurgent second half from Alex Bregman.

The pitching issues are coming from every direction. Cade Horton, Justin Steele, Edward Cabrera and Ben Brown have all missed major chunks of the year.

Steele still has not made his 2026 debut, Horton made only two starts before season-ending surgery, and Brown’s breakout was derailed by a recurring neck injury. Cabrera may still be part of the bullpen down the stretch, but even when he has been available, he has not given Chicago nearly enough.

The bullpen hasn’t escaped the carnage either. And while injuries have played a huge role, they don’t explain everything. A lot of Jed Hoyer’s offseason work aimed at stabilizing the staff has simply not held up.

Jacob Webb has been the bright spot, and he’s been excellent. But his success hasn’t been enough to cover for the struggles and injuries that have hit Hunter Harvey and Phil Maton, Chicago’s two highest-paid relievers. Cabrera, acquired in the January deal that sent top-100 prospect Owen Caissie to the Marlins, also has fallen short of expectations since arriving.

The result is ugly. The Rockies’ pitching staff, despite playing half its games at Coors Field, has been nearly twice as valuable as the Cubs’ group. And yet Chicago is still on the verge of securing a second straight postseason berth.

That should tell you how much the offense has carried this team. It also makes the October outlook pretty clear: unless the Cubs get late-season reinforcements that can change the story in a hurry, that pitching staff is the kind of weakness that can send them home fast.

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