Brian Cashman has never been shy about making bold moves for the Yankees, and his next power play may already be in motion. According to insiders, the Yankees’ longtime general manager is keeping a close eye on Pittsburgh Pirates ace Paul Skenes, preparing to swoop in the moment the small-market club hesitates on paying up.
Skenes, the No. 1 overall pick in the 2023 MLB Draft, has already flashed elite potential with a triple-digit fastball and dominant strikeout ability. He’s expected to be the cornerstone of Pittsburgh’s rotation for years to come—assuming the Pirates are willing to spend what it takes to keep him. But history suggests they won’t.
Pittsburgh has a long track record of failing to hold onto their homegrown stars. Gerrit Cole, Tyler Glasnow, and Josh Bell all left town, and Pirates ownership has consistently prioritized cost-cutting over title contention. That’s exactly why Cashman is positioning the Yankees as a prime destination for Skenes once Pittsburgh inevitably fumbles their opportunity.
The Yankees, who have long valued power arms, could view Skenes as their next ace in waiting. With Gerrit Cole anchoring the rotation, adding Skenes to the mix would give New York a lethal 1-2 punch for the future. And if Pittsburgh shows any hesitation in offering Skenes a massive extension when the time comes, Cashman will be ready to pounce—whether through a blockbuster trade or by luring him in free agency down the line.
This wouldn’t be the first time the Yankees capitalized on another team’s financial limitations. They famously poached Cole from Pittsburgh and later signed him to a record-breaking deal. With Skenes, the opportunity could play out the same way.
For now, the Pirates still control Skenes’ future—but everyone around the league knows how this story tends to end. Cashman is playing the long game, waiting for Pittsburgh to fold. And when they do, the Yankees will be ready to strike.
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