Chicago Cubs wild trade proposal brings All-Star ace to Chicago

The story of this offseason for the Chicago Cubs will be pitching. And whether 2027 is a massive success or disappointing failure will likely hinge on how well their pitching pursuit goes this winter/spring.

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As things stand right now, the team’s rotation is fragile and full of question marks. Justin Steele heads the rotation after nearly two years lost due to elbow surgery. Behind Steele are Ben Brown—who was shut down in June due to recurring neck issues after what was shaping up to be a breakthrough season—and the injury-plagued, wildly inconsistent Edward Cabrera, with Javier Assad and Braxton Garrett also vying for a rotation spot.

That’s hardly a championship-level starting rotation.

The Cubs will definitely dip into the free agency market to fortify their starting pitching. They may look to Japan for signable arms. They will look to cash in with a reclamation project or two, as Cubs president Jed Hoyer likes to do each season.

They’re also likely to explore trades.

Chicago has already been tied to the Seattle Mariners when it comes to offseason swaps. However, another potential trade partner has been brought to the public—the Tampa Bay Rays.

Drew Rasmussen?

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Specifically, the Rays’ ace Drew Rasmussen has been mentioned as a potential target.

According to Jeff Passan of ESPN, Tampa Bay may be tempted to deal the two-time All-Star due to budgetary reasons.

The 31-year-old righty, who will become a free agent after next season, has seen his salary balloon from $8 million to $20 million after the Rays exercised their club option on him for 2027. But having exercised that option doesn’t necessarily mean that they intend to keep him.

Rasmussen is a true top-of-rotation ace who hasn’t posted an ERA above 3.00 since his 2020 rookie season. Last year, he went 16-5 and delivered a 2.67 ERA through 30 starts and 172 innings pitched.

Grabbing Rasmussen on a $20 million salary—even for a single-season—would be a superb pickup, especially if it came along with an elite-tier free agent pitching acquisition.

The Cost

But what would the Rays want in return for their ace? Do the Cubs even have the trade chips anymore to pull off a deal like this?

Rich Eberwein of Cubbies Crib recently proposed a trade that he feels might get the Rays thinking about pulling the trigger on a Rasmussen deal:

“The Cubs would need to serve up at least two MLB-ready arms in this hypothetical trade. Maybe a package including Javier Assad, Jaxon Wiggins, and a lower-tier pitching prospect would make sense. The Rays would be flipping Rasmussen for three controllable pitchers, and the Cubs would have their ace for the 2027 season without completely gutting their pitching depth.

The Cubs would be acquiring a guy who has a 2.71 ERA (322 innings pitched) since the beginning of the 2025 season.”

Eberwein’s trade proposal might be a bit light, to be honest. The Rays might want one of the Cubs’ stud prospects in the deal, like Josiah Hartshorn, along with Wiggins, Assad, and maybe someone else. That could be a deal-breaker for Chicago. But if they’re really keen on winning in 2027, maybe not.

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