Deadlines don’t care about comfort zones, and neither do division rivals on an 11-game heater. The Chicago Cubs may be winning games, but the real scoreboard is inside the front office. While fans chant for October glory, ownership clutches its pen when it comes to extensions. Meanwhile, the Milwaukee Brewers aren’t waiting around—they’re stacking wins, arms, and pressure on Jed Hoyer’s already smoldering seat.

When you are a top team, the expectations and the hope resting on your shoulders are big. Even a small slip-up or a bad signing can derail an entire season, and the Cubs can’t afford that with them having a good season. But they can’t sit back and delay important decisions till the last minute, especially with the Brewers running through teams.

In a recent The Athletics’ article, MLB insider Jim Bowden talked about some of the front office executives who are under pressure. He mentioned the Cubs and Hoyer in the list. He said, “Hoyer and his GM, Carter Hawkins, are signed through the 2025 season… deserve contract extensions for the great job they’ve done in hiring manager Craig Counsell… However, if ownership hasn’t extended their contracts by now, there’s pressure on both to keep adding at the deadline.”

The Cubs are thriving on the surface, but pressure is boiling just beneath the wins. With a 59-41 record and an 88.5% playoff chance, the team is a contender. Yet as October looms, every decision carries weight, and hesitation now could haunt them later. In a red-hot NL Central race, inaction feels less like caution and more like a gamble.

Hoyer, signed through 2025, has rebuilt this roster impressively but faces his defining deadline. Despite back-to-back 83-79 seasons, ownership has withheld extensions for both Hoyer and GM Carter Hawkins. That quiet refusal sends a loud message: prove it now or risk replacement later. Without trust at the top, bold moves often die at the drawing board.

The Cubs’ hesitance isn’t just about front office contracts—it extends to trade philosophy and deadline aggression. In past seasons, despite clear needs, they avoided splashy moves that might have shifted momentum. Now with Justin Steele out and the bullpen thin, another passive summer could be fatal. Even Buster Olney noted: the question isn’t October entry—it’s October survival.

Meanwhile, the Brewers have won 11 straight, adding Jacob Misiorowski and Brandon Woodruff to their arsenal. As Milwaukee charges, the Cubs must decide whether to chase or collapse under conservative instinct. Holding trade chips like Owen Caissie and Kevin Alcantara means options exist—if only they choose courage. In baseball’s tightest windows, fear of the future is often the cost of greatness.

But baseball doesn’t crown the cautious—it punishes them with early exits and “what if” regrets. The Cubs have the roster, the momentum, and the fanbase begging for action, not apologies. If Hoyer and company want job security, they might need to trade like their jobs depend on it. Because while Chicago debates extensions, Milwaukee is extending leads, and October won’t wait for hesitant heroes.

It might not be enough, but the Cubs to start somewhere with trades

At some point, “being patient” starts to look a lot like standing still. The Chicago Cubs are staring down a playoff opportunity with a rotation patched together by hope and duct tape—and the front office brass still hasn’t been handed new contracts. Jed Hoyer’s signature move this year? Restraint. Now, with pressure mounting and the rumor mill heating up, restraint might finally meet its expiration date.

The Cubs’ rotation has cratered without Justin Steele and Shota Imanaga available this season. Their starters have limped through the first half, prompting a recall of Ben Brown from Triple-A for emergency coverage. With Steele out for season-ending elbow surgery, the front office looks desperate for veteran help. General manager Hoyer’s patience is wearing thin as contract extensions remain unsigned.

Enter Sandy Alcantara—a former unanimously voted Cy Young ace whose 2025 ERA sits around 7.14 over 20 starts. Despite struggles, advanced metrics like a 4.99 xERA hint at hidden upside awaiting refinements. A midseason acquisition could stabilize Chicago’s rotation and spark a playoff push this year. Plus, securing him under team control for the next two seasons offers long-term upside and cost certainty.

The Cubs can’t duct tape their way to October glory—not in this division, not now. Hoyer’s front office has flirted with urgency but is committed to little more than calculated stalling. If this is truly their window, then it’s time to stop window shopping. Alcantara may not be perfect, but perfection rarely hits the trade block. Sometimes, winning starts with admitting that patience isn’t a plan—it’s an excuse.