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Report: Chicago Cubs willing to trade top prospect in deal for division rival starter

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Chicago Cubs

Once again, the word “desperate” has popped up to describe the Chicago Cubs’ trade deadline pursuit of starting pitching.

In a recent summary of deadline chatter and updates, Bob Nightengale of USA Today mentioned the Cubs’ continued interest in the Pittsburgh Pirates’ Mitch Keller and how much they may be willing to give up for the right-hander.

Per Nightengale:

“The Cubs desperately want another starter at the deadline, targeting Mitch Keller of the Pirates, and would include outfield prospect Owen Caissie to make it work.”

Owen Caissie, trade bait

Syndication: The Des Moines Register,Owen Caissie, Chicago Cubs
Syndication: The Des Moines Register Iowa Cubs’ Owen Caissie (17) makes his way to the dugout on Friday, March 28, 2025, at Principal Park in Des Moines. © Cody Scanlan/The Register / USA TODAY NETWORK via Imagn Images

The 23-year-old Caissie, Chicago’s no. 1 prospect, is widely regarded as the team’s top piece of trade capital and has been rumored in deals since the offseason when the team pursued the Miami Marlins’ Jesus Luzardo before abandoning the deal due to a dubious Luzardo physical.

It’s been widely reported, though, that Cubs president of baseball operations Jed Hoyer is unwilling to move the power-hitting corner outfielder for a rental player. Caissie factors into the team’s plans when/if they can’t re-sign Kyle Tucker after this season and the Cubs would have to get a player with years of team control to give up that right field insurance policy.

Chicago Cubs pursuing team-controlled pitchers

Chicago Cubs trade target Mitch Keller throws a pitch.
May 2, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates starting pitcher Mitch Keller (23) throws a pitch during the first inning against the San Diego Padres at PNC Park. Mandatory Credit: David Dermer-Imagn Images

The 29-year-old Keller is signed through 2028 on a contract worth about $55.5 million. He’s currently having a career year with a 3.53 ERA in 21 starts, but his career ERA is right around the 4.40 mark. His ground ball-inducing pitch arsenal is projected to go over well at Wrigley Field, with the elite-level Cubs defense working behind him. His durability is also a plus as he’s passed 30 appearances his last three seasons and is on pace to do so again this year.

Keller would look good slotted between lefties Shota Imanaga and Matthew Boyd and he’d definitely be an improvement over Colin Rea or Ben Brown in the rotation.

But the Pirates are surely fielding other offers for Keller and the asking price will go up as high-end starters begin to disappear off the trade market.

Feeling the heat

Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel.
Jan 12, 2024; Chicago, IL, USA; Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel. Mandatory Credit: Kamil Krzaczynski-Imagn Images

No doubt, the Cubs are feeling the heat, though.

One source of heat is coming from the Milwaukee Brewers, who caught the Cubs atop the NL Central Division, passed them, and now are tied with them in first place.

The other heat is coming from the ticking clock as the July 31 trade deadline nears and they’ve yet to fill any of the roster holes targeted.

The goal for much of the season, once it was established that this Cubs team had some magic motoring them, was a deep playoff run and maybe even a World Series appearance. The goal right now is to stave off the red-hot Brewers and actually GET to the postseason.

Either way, the team needs some key pickups to ensure they get where they want to go.

Chief among their needs is starting pitching, as the battered and strained rotation has started to come apart at the seams.

There’s little hope for big postseason success when everything past your top two starters is a question mark and/or a cross-your-fingers proposition. The Cubs are in an especially precarious situation when one of those two top starters, Boyd, has a history of injury and hadn’t thrown more than 100 innings since 2019 and the other, Imanaga, showed a 2 mph dip in velocity during his most recent (awful) outing.

The feeling is that something will give when it comes to the Cubs’ pursuit of starting pitching. They should get somebody to plug up a hole there and they’ll most likely give up Owen Caissie in order to do that.


Source: https://www.chicitysports.com/chicago-cubs-trade-pirates-keller-caissie?utm_source=rss&utm_medium=rss&utm_campaign=chicago-cubs-trade-pirates-keller-caissie


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