Cubs Ready to Deal "Majority" of Top Prospects as Big Trade Deadline Looms

As if it wasn't clear already, the Chicago Cubs are ready to push their chips in.

The organization is built to win now and holds a 59-46 record on the season. While the beginning of the 2026 campaign had high highs and low lows, they have stabilized over the last month and a half. They have undoubtedly performed like one of the most consistently competitive teams in the league, appearing more than worthy of a playoff spot.

To be sure, they still do find themselves 6.0 games back of the Milwaukee Brewers for the NL Central lead. But it's still an impressive place to be, specifically when considering they have also been among the most banged-up groups in baseball. The organization has watched a shockingly long list of pitchers hit the IL, including multiple starters.

This is why it feels like the Cubs can still take a meaningful step forward before the postseason. The trade deadline will present an obvious opportunity to land some significant upgrades, especially in the pitching department. There is an impressive list of starters expected to be made available over the next week, and the Cubs sound willing to pay the price to bring one of them to the Friendly Confines.

Just ask ESPN's Jeff Passan!

Cubs Sound Ready to Make a Big Splash

If the Chicago Cubs made one thing clear on Monday, it's that they mean business in 2026. The team shockingly decided to DFA veteran starter Jameson Taillon. To be sure, he became a true liability on the mound, but it was still the kind of drastic decision we haven't necessarily seen Jed Hoyer make in the past.

Could more be on the way? It's been difficult to get a read on just how willing the Cubs would be to trade some of their top prospects. However, Jeff Passan shared on Threads this week that essentially all of the Cubs' top minor leaguers are up for grabs. And they are even open to discussing some of the names on their major league roster.

"They're willing to deal off their major league and minor league rosters," Passan wrote in a Threads Q&A. "While I think Josiah Hartshorn is off-limits, a majority of their prospects will be available, whether that's Wiggins, Ramirez, Rojas, Kepley, Ayers, etc. The Cubs are going to get at least one starting arm -- and, good for them, it's the most bountiful position on the market."

Now, does this mean the Cubs will give up Top 10 prospects like Jaxon Wiggins, Jefferson Rojas, and Owen Ayers in any deal that solves a major league problem? No. They're likely going to be picky. But the fact that they are sending the message that everyone is on the table should only help generate better conversations. If they were being more picky, certain teams might hang up the phone. This is especially true if we're talking about potential like Joe Ryan or Tarik Skubal.

Speaking of which, Passan did specifically touch on those two arms. While it didn't seem to be a hard no, he admitted that he doesn't expect this to be where the Cubs ultimately land.

"I think they know they'd have to gut their system for either Skubal or Ryan, and I don't think that's something they're willing to do," Passan wrote. "Maybe if Matt Shaw is part of such a package, they could swing it, but if they're holding Josiah Hartshorn, it's going to take more. The important question here that we don't know the answer to is whether the Tigers and Twins are seeking a smaller package with better-regarded prospects or whether they want to go pure volume."

Considering how many starting pitchers are expected to be available, it's not all that surprising to hear that the Cubs may play it a little safe. Every team would obviously prefer to fill in the gaps while holding onto some of their top prospects. A trade with the Angels, in particular, feels like a way the Cubs could accomplish this. Los Angeles may value catcher Owen Ayers more than others.

Nevertheless, the Cubs are in clear win-now mode. They have been a tad hesitant in the past to go all-in and look like one of the league's more aggressive squads. With that in mind, the simple fact that they appear as open as they are is encouraging. It gives us further confidence that a couple of significant moves could be made over the next week. Buckle up!

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