Jed Hoyer Faces Defining Cubs Test As October Pressure Builds

The Cubs' 2026 season hinges on overcoming injuries, maintaining player momentum, and strategic trade decisions as they pursue a playoff berth.

The Cubs head into the second half with a solid base under them, but the next few months will decide whether this turns into a real run or just another season with promise. They’re 54-42 at the break, five games behind the Brewers in the NL Central and 3 1/2 games up in the NL Wild Card race.

The standings give them a path. The injuries give them a warning label.

That’s been the story of the first half: health issues everywhere, especially on the pitching side. And if the Cubs are going to finish strong, three things have to break right.

Pete Crow-Armstrong has been one of the biggest reasons the Cubs are still in this position. In 96 games, the center fielder has piled up 21 homers and 24 steals while flashing his usual elite defense, good for 6.0 fWAR and 5.8 bWAR. That’s the kind of first half that puts a player right in the NL MVP conversation.

But Cubs fans have seen a version of this movie before. Crow-Armstrong went into last year’s All-Star break with 25 homers, 27 steals and 4.6 fWAR, and he was being talked about like an MVP candidate then, too.

The second half told a different story. He hit just .216 with six homers and eight steals the rest of the way, which is exactly why there’s some natural concern about a repeat.

If that kind of drop-off happens again, it would be a serious problem for Chicago’s playoff hopes. This year’s team doesn’t have the same pitching depth as the 2025 club, so it can’t as easily survive a quiet offense.

Still, there’s reason to believe Crow-Armstrong’s numbers are sturdier this time around. As MLB.com's Jordan Bastian recently pointed out, his 2026 production has come with much stronger on-base numbers than he showed in 2025.

The Cubs also need Jed Hoyer to be aggressive at the deadline, because the pitching situation is staring them in the face. Last year’s deadline left fans wanting more after the team came away with Michael Soroka and Andrew Kittredge. Kittredge helped down the stretch, but Soroka barely pitched and wasn’t the front-line starter many expected.

This summer’s need is even more obvious. The Cubs are short on arms in both the rotation and the bullpen, with Cade Horton done for the year, Justin Steele out for the foreseeable future, Ben Brown still uncertain, and Daniel Palencia not yet throwing off a mound. That leaves them without, arguably, their four most impactful pitchers.

Jed Hoyer has long been known for keeping one eye on the future, so even with Tarik Skubal’s name floating around, a blockbuster would be a surprise. But there are other options who could matter.

Sonny Gray, Robbie Ray, Eduardo Rodriguez and Casey Mize would all help the rotation, even as rentals. If the Cubs want a bigger swing, controllable names like Reid Detmers and Logan Webb would be even more appealing if they can be pried loose.

If Hoyer stays quiet, it’s hard to see how this staff gets where it needs to go by October.

Then there’s Alex Bregman, the big-money addition who still has to look like one. The Cubs made their expectations clear when they gave him one of the largest contracts in franchise history, but so far he hasn’t matched it. He’s hitting just below league average, and his 2.3 bWAR and 1.7 fWAR are a long way from the All-Star level he delivered for Boston last season.

The good news for Chicago is that Bregman finished the first half with a strong burst. Over his final nine games before the break, he had four doubles, two home runs and a strikeout rate of just 12.5 percent. During that stretch, he was 21 percent better than league average at the plate by wRC+.

If that power uptick carries over, the Cubs have a much better chance of making a push. Bregman posted a 125 wRC+ last season, and if he gets closer to that version of himself in the second half, Chicago’s lineup gets a lot more dangerous.

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