Skip to main content

Jeff Passan's Cubs trade deadline fits mirror Jed Hoyer's biggest debate

Is it worth going big at the deadline this year?
May 26, 2026; Pittsburgh, Pennsylvania, USA;  Chicago Cubs president of baseball operations Jed Hoyer observes batting practice before the Pittsburgh Pirates host the Cubs  at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
May 26, 2026; Pittsburgh, Pennsylvania, USA; Chicago Cubs president of baseball operations Jed Hoyer observes batting practice before the Pittsburgh Pirates host the Cubs at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

Despite their rollercoaster season to this point, the Chicago Cubs are 12 games above .500 at the All-Star break, and in firm control at the top of the Wild Card race. A decent position in the standings shouldn't translate to complacency, however, as Chicago remains well behind Milwaukee in the NL Central. That's going to put plenty of pressure on Jed Hoyer and his front office to supplement the club ahead of the trade deadline.

With the deadline just a few weeks away, it's clear what the Cubs need at this point. Chicago's position player group is hard to argue with at this point. They're the best defensive squad in MLB and trail only the Dodgers in terms of wRC+, putting them in a position so strong they could actually considering dealing from the MLB roster this summer. That leaves all eyes on the pitching staff, and ESPN's Jeff Passan was quick to make clear in a recent article that the Cubs need a starter.

Both of Passan's fits for Chicago, unsurprisingly, are starting pitchers. The injuries that have wiped out most of the Cubs' pitching staff throughout this year are well-documented at this point, from Cade Horton and Justin Steele to Ben Brown and Edward Cabrera. Red Sox veteran Sonny Gray is described by Passan as the Cubs' "dream fit," and he's already been discussed heavily as a potential target. Tigers right-hander Casey Mize would be just as intriguing as an alternative, however.

Jeff Passan clocks potential issues with Cubs' Sonny Gray pursuit

It's a good thing that Mize, who sports a 2.79 ERA and 2.69 FIP through 14 starts this year for Detroit, is such an attractive secondary option for the Cubs. That's because Passan dumped cold water on Cubs' fans hopes of landing Gray in his article. While he acknowledges that Gray would be a perfect fit for the Cubs' needs, he also notes that there's other factors at play that could give the team pause about pursuing the veteran righty.

For one thing, Gray has a no-trade clause. That means he would have to green-light any trade to the Cubs, and while the two-time NL Central veteran shouldn't have any qualms about playing in the Midwest, it's at least possible he'll try and use that leverage to pitch elsewhere. Even if Gray were to approve a trade, a bigger issue is the financials attached to the veteran's deal. Gray is owed $10M in salary with an additional $10M owed as a buyout on a mutual option for the 2027 season.

Mutual options are almost never exercised, meaning it's effectively a $10M anchor attached to Gray. That's good for the prospect cost, but it raises questions about if Hoyer will even be allowed to pursue him. While Tom Ricketts has previously stepped in to greenlight pricey deadline moves like the Nick Castellanos trade, that was now almost a decade ago. The purse strings have been much tighter in recent years, and after this offseason's spending spree ownership's generosity may dry up.

Add us as a preferred source on Google

Loading recommendations... Please wait while we load personalized content recommendations