Chicago Cubs: Insider targets “perfect fit” for Cubs trade deadline shopping

The Chicago Cubs have now officially begun their second-half push to the postseason and are inching closer to what many feel is a make-or-break August 3 MLB trade deadline.

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With a full staff of pitchers on the shelf due to injury and uncertainty swirling all about, the team needs to make some impact acquisitions at the deadline if the goal is to do anything of note in the playoffs. There’s no guarantee that they will even make the playoffs if their patchwork pitching staff can’t be significantly reinforced.

Cubs president of baseball operations Jed Hoyer has already gone on record as saying that pitching will pretty much be their sole focus heading into the deadline. The question is who Chicago will target and whether they’ll truly go “all in” when it comes to landing an impactful arm or two.

Lots of names have been tossed about by media and fans, mentioned as fits for a needy Cubs team. Ideally, the Cubs would like a younger pitcher with years of team control remaining after this season. But, given their need and the reality that the trade market may be much tighter than anticipated, they may have no choice but to go for a rental or two.

Robbie Ray, perfect fit?

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Bob Nightengale of USA Today feels that Robbie Ray of the San Francisco Giants is a perfect fit for the team and its particular needs.

Per Nightengale:

“But if they’re going to be a serious challenger to the big boys in the National League, they’re going to need some more pitching. To be specific, a big-time starter, with San Francisco Giants No. 2 starter Robbie Ray being a perfect fit. They are expected to have Jameson Taillon return this week, and Edward Cabrera in three weeks, but they can’t afford to wait. They could use bullpen help, too, with closer Daniel Palencia sidelined until at least mid-August.”

The 34-year-old left-hander is in the last year of his contract and will be headed to free agency at the end of this season. On the year, he’s 8-6 with a 3.38 ERA in 106.2 innings over 19 games.

Right off the bat, bringing in Ray would give the Cubs a durable starter who can give the team innings. On the current roster, only Shota Imanaga has amassed more innings pitched this season (108) than Ray (106.2).

When working at full capacity, the 13-year veteran can provide some ace-level work. Over the course of his career, he has a 3.90 ERA. Tommy John surgery in 2023 may have made his workhorse reputation a thing of the past, but he bounced back with 182.1 innings in 2025 and is on his way to a respectable workload this season as well.

But…

A point of concern, though, is that Ray can give up the long ball and is currently working below league average in home runs per nine innings with a 1.27 rate. He’s not exactly Imanaga in that regard, but he can be touched.

With starting pitching at a premium this deadline, the Giants may also be asking a lot for the veteran. At some point, it just wouldn’t make sense to give up premium prospects for a 3-month rental on a team that would still need some true good fortune to get though its pitching issues.

Time will tell what the Cubs do at this trade deadline.

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