Chicago Cubs: Sonny Gray AND Aroldis Chapman in one wildly bold trade?

The Chicago Cubs managed to hold on for dear life Sunday against the Milwaukee Brewers at American Family Field and cinch a series win.

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In a bullpen game that was started by Ryan Rolison and ended by a cross-your-fingers Jordan Wicks, who came in with the bases loaded and no outs in the tenth inning, holding on to a 4-3 win felt like a World Series Game 7 victory.

But, realistically, the law of averages says that the Cubs can’t keep the spinning plates on the sticks forever and that, sooner or later, there will be lots of loud crashes.

Hoyer’s daunting shopping list

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That’s why the August 3 trade deadline is of extreme importance when it comes to the team’s chances of even getting to the postseason.

The beleaguered starting rotation is, rightfully, getting most of the attention. They are, after all, currently minus three of their five projected starters at the start of the season (Taillon, Cabrera, Horton) and two of those counted as depth pieces (Brown, Steele).

But the bullpen also needs some serious attention.

Currently on the shelf are closer Daniel Palencia, as well as three of the four incoming free agents signed by the team to make up the bulk of the high-leverage relief appearances (Maton, Milner, Harvey). And per the most recent report, Palencia’s return is not even on the table until some point after the All-Star break.

Cubs president of baseball operations Jed Hoyer will have a pretty stressful shopping list come deadline.

Ryan O’Rourke of Cubbies Crib recently introduced the idea of a possible one-stop shopping spot for the Cubs—the Boston Red Sox.

Gray AND Chapman to the Cubs?

Specifically, the idea of possibly targeting starter Sonny Gray and former Cubs closer Aroldis Chapman in a package deal was mentioned:

“It would be costly, but one option to kill two birds with one stone might be to approach the Red Sox for a package deal with Aroldis Chapman and Sonny Gray, giving the Cubs a solid rental starter and an old friend who’s still pitching like one of the best relievers in the sport with a 1.90 ERA. Chapman’s also likely to hit his $13 million vesting option, meaning they’d have him for another year at a reasonable cost.”

Well, that’s certainly not a two-man haul Chicago should immediately rule out, especially considering their needs.

The Cubs could very well be dealing a good chunk of prospect capital for what could be a pair of three-month rentals (both Gray and Chapman—if Chapman qualifies for his vesting option—would be in a mutual option situation that would probably see both opt for free agency).

But what they could provide to the team in the final stretch of the 2026 season could be a serious difference-maker.

Gray is a legit front-of-rotation ace who is pitching like an ace this season with a 9-1 record and a 2.69 ERA for a very bad Red Sox team. Chapman, meanwhile, is still throwing fire at 38 years of age, currently posting a 2.19 ERA with 16 saves over 26 appearances. Aside from providing support to Palencia, it would just be kind of cool to have a key component of the Cubs’ 2016 World Series team back on the squad.

The cost of such a deal would be high. Matt Shaw could likely be part of the deal, as well as a top Triple-A prospect or two, and some lower-level young talent.

So, would trading away Shaw, Moises Ballesteros/Jefferson Rojas, and a pair of high-end A-ball assets be worth a rental of Gray and Chapman? It might be, if the Cubs feel they have a real chance of doing something big in the postseason.

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