Chicago Cubs: A trade deadline shocker could become reality, per analyst

The Chicago Cubs are heading into the 2026 season with great expectations and a feeling that this year could most definitely be their year. Part of the reason for such optimism is in the fact that their starting rotation is so deep and locked in.

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Barring some unforeseen surprise, the Cubs will start the season with a rotation of Matthew Boyd, Cade Horton, Edward Cabrera, Jameson Taillon, and Shota Imanaga. Then, possibly as early as May or June, Justin Steele should be coming back from last year’s elbow surgery.

That would give the team six viable starters, plus Colin Rea and Javier Assad as capable swingmen who could step in and take a rotation spot for a good period of time.

So, what would Chicago do with six starters (or possibly eight) and only five slots in which to put them?

An unprecedented trade

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Jake Misener of Cubbies Crib predicts that the Cubs could trade one of them away at the trade deadline for whatever they may need to take them comfortably into the postseason.

Per Misener:

“…Nobody is doubting the sheer volume of arms in the mix here. Cabrera and Horton are joined by Jameson Taillon, Matthew Boyd and Shota Imanaga – as well as Javier Assad, Colin Rea and Ben Brown, not to mention Justin Steele, who is expected to return in May or June.

That math doesn’t math – at least not when everyone is healthy. There could be a deal out there this summer to the Cubs’ liking, maybe to add a bona fide late-inning arm, and seeing Hoyer deal from a position of strength makes a decent amount of sense.”

Dealing from a position of strength

It’s unprecedented for a likely playoff-bound team to trade AWAY a starter at the deadline. However, if the Cubs’ rotation stays healthy and Steele can return to ace-level form, the front office, as Misener says, could cut a deal from a position of strength.

Maybe they’d get a bullpen stud, someone who could add some end-of-game stability and step into a closer or co-closer role. Maybe the acquisition could be a proven power hitter.

Of course, such a deal would probably mean that their trade partners would also see themselves as contenders for postseason play. So, a trade like that would require some boldness from both sides.

But, why not? Imanaga and Taillon are free agency-eligible at the end of the season. Boyd, meanwhile, is staring down a mutual option at the end of 2026 and is not an absolute guarantee to return next year.

In a Cubs-perfect world, the team would still be carrying five starters into August with some solid backup behind them.

First, though, the Cubs have to stay healthy and live up to expectations. If not, any deadline trades would be sell-offs and not roster reinforcement.

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