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ESPN insiders pull back the curtain on Cubs’ true deadline strategy

Cubs’ trade deadline secrets finally come out thanks to ESPN insiders
ByJordan Campbell|
Jul 18, 2025; Chicago, Illinois, USA; Chicago Cubs President of Baseball Operations Jed Hoyer walks on the sidelines before a baseball game between the Chicago Cubs and Boston Red Sox at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
Jul 18, 2025; Chicago, Illinois, USA; Chicago Cubs President of Baseball Operations Jed Hoyer walks on the sidelines before a baseball game between the Chicago Cubs and Boston Red Sox at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

If the Chicago Cubs had their wish, they likely would have added a top-of-the-rotation starting pitcher to their rotation before their series against the Milwaukee Brewers. The worst-kept secret is that the Cubs will be adding a starting pitcher before Thursday's trade deadline, but it remains to be seen if they will be able to land a controllable ace to boost their rotation during the closing months of the season.

As the baseball world prepares for the deadline, ESPN's collection of baseball insiders pulled the curtain back on why the Cubs haven't made a move yet. Buster Olney mentioned that the Cubs are effectively looking to replace Justin Steele ahead of the postseason, but the price remains the biggest roadblock.

"The Cubs would love to add a front-line starting pitcher, someone who could effectively replace Justin Steele in their rotation. But maybe more than any team, they could be hamstrung by how thin the market is unless they value the cost of acquiring Joe Ryan or Cease or if they work something out for Merrill Kelly."

Jesse Rogers had a more Cubs-centered look at the deadline, suggesting that the expectation remains that the front office will be relatively aggressive ahead of Thursday. The biggest question is how willing Jed Hoyer will be to add a frontline starting pitcher. In other words, will Hoyer be willing to move any and all top prospects to accomplish that goal?

ESPN insiders reveal what’s really happening inside the Cubs’ front office

It seems that the Cubs are in a staring contest with teams like the Miami Marlins when it comes to adding a starting pitcher who is under control beyond this season. The Marlins have Edward Cabrera, who could easily slot near the top of the Cubs' rotation. The issue is that the Marlins are holding out for Owen Caissie and Jaxon Wiggins, and it doesn't seem that Hoyer is willing to deplete the farm system to that extent.

Thursday is going to be a decisive moment for Hoyer. Freshly extended, it will be the first look at whether Hoyer will still approach the deadline with the type of urgency he had when he traded for one season of Kyle Tucker last winter.

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