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Blockbuster Cubs-Pirates Trade Idea Lands Cy Young Contender

Originally posted on Athlon Sports | By Conor Liguori | Last updated May 22, 2025 12:55 PM ET

After the Pittsburgh Pirates’ poor start to 2025, the fanbase wonders what the front office will do with its best player.

Of course, that player is starting pitcher Paul Skenes, 17th in Major League Baseball with 62 strikeouts and a top contender for this year’s National League Cy Young Award.

Many clubs could be interested if the Pirates make Skenes available in trade discussions at the deadline.

The Chicago Cubs are one of MLB’s potent offenses, but the starting rotation has left much to be desired after injuries to Justin Steele and Shota Imanaga.

On Thursday, Bleacher Report’s Zachary Rymer proposed a trade idea that would send Skenes to the Cubs to revamp their rotation.

Rymer listed the Pirates’ return as third baseman Matt Shaw, right-handed pitcher Cade Horton, and outfielder Owen Caissie. All three are top-five prospects in the Cubs’ organization.

“Sustaining the Cubs has been an offense that leads MLB in scoring even without much help from Shaw, who has a .610 OPS to show for 77 plate appearances, “ Rymer wrote.

“He is, therefore, an acceptable sacrifice, and ditto for Horton if it means putting Skenes in his place.”

Although a trade for Skenes would be ideal for the Cubs, Rymer acknowledges that a deal of that magnitude is easier said than done.

“It's an iffy proposition, particularly given that the Pirates could potentially balk at the return,” wrote Rymer.

“Shaw has shown a ton of swing-and-miss at the major league level, while Horton is coming off an injury-marred year in the minors.”

For the Cubs, acquiring Skenes with several years of control may apply even more pressure on the front office to extend outfielder Kyle Tucker, or reach a deal with him when he reaches free agency at the end of the season.

This article first appeared on Athlon Sports and was syndicated with permission.

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