ESPN insiders believe Cubs are ready for unprecedented Jed Hoyer deadline move

Back in early June, when the Chicago Cubs were swooning and rapidly falling out of the National League playoff picture, Jed Hoyer told us that his team needed to play better over the ensuing weeks in order for him to justify buying at the trade deadline. The locker room clearly got the message, as the North Siders currently hold the top NL Wild Card spot and are one of just five clubs with at least 57 wins on the season.

Now, it's on Hoyer to hold up his end of the bargain. We all know he has to acquire one, if not multiple, starting pitchers. It'd also be nice if he could insulate the bullpen from any further injury, and another slugging option off the bench wouldn't hurt either.

That's a pretty sizable shopping list for a 10-day stretch during the middle of the season. It's also not in Hoyer's wheelhouse to make multiple impact additions in the same window; for better or worse, he loves to play the market and let the value come to him.

And yet, two of ESPN's top MLB insiders (Jeff Passan and Buster Olney) believe that the Cubs will be among the most aggressive and active teams leading up to the deadline.

Jed Hoyer has spent years building a reputation Cubs fans hope he'll destroy at the trade deadline

While it's nice to hear industry veterans express mutual agreement on this topic, it's really hard not to look at Hoyer's track record and doubt their expertise. Most of his time running the front office has involved selling, incluiding the 2021 fire sale and a bizarre 2022 trade deadline where he refused to move Willson Contreras and Ian Happ after months of speculation.

Arguably his biggest buy-side move during the season remains the acquisition of Jeimer Candelario in 2023, which didn't really pan out since the ahead-of-schedule Cubs missed out on the playoffs. It should also go without saying that this year's team needs far more than a Candelario-esque move to compete with the heavyweights in the National League.

Our most recent data point, the 2025 trade deadline, really suggests that Hoyer isn't capable of the kind of aggression that ESPN is predicting. That team was closer to the top of the NL Central standings than the 2026 one, and yet the president of baseball operations could only bring himself to acquire two low-cost relievers (Andrew Kittredge and Taylor Rogers), a swingman (Michael Soroka), and a utility bench player (Willi Castro).

With a lockout looming and the unbeknownst economic ramifications that will follow, Hoyer will be walking a tightrope this year. On one hand, you'd think he'd be ready to go all-in on this core, doing whatever he can to extend the season as long as possible before everything is shut down. On the other, it wouldn't be a surprise for him to excercise extreme caution as he eyes nothing but uncertainty ahead.

Passan and Olney clearly believe he'll pick the former. As Cubs fans, it's nearly impossible to expect anything but the latter.

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