Inside The Pinstripes

Paul Skenes Wants to Play for Yankees?

Imagine a world where the New York Yankees acquire Paul Skenes from the Pittsburgh Pirates?
Sep 16, 2025; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates starting pitcher Paul Skenes (30) pitches against the Chicago Cubs during the third inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Sep 16, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates starting pitcher Paul Skenes (30) pitches against the Chicago Cubs during the third inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

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If there is a baseball equivalent of Luka Dončić getting traded to the Los Angeles Lakers, it's Paul Skenes to the New York Yankees. It's an idea that, until now, has only existed in MLB The Show and on faceless social media accounts run by fans touting the Bronx Bombers as their favorite team.

The Rumor Mill

The noise around Skenes and the Yankees might get louder, though. Especially after Randy Miller of NJ.com dropped a nugget about Skenes privately hoping he finds himself playing alongside Gerrit Cole, another former member of the Pittsburgh Pirates, and the captain, Aaron Judge.

"Trust me, he wants to play for the Yankees," an anonymous teammate of Skenes told Miller. "I've heard him say it multiple times."

Pirates General Manager Ben Cherington was asked about the rumor. He shot it down.

"I do dismiss it, but I understand it," Cherington said, according to Miller. "What we're going to focus on is just how do we win games with him in a Pirates uniform. I have a ton of respect for the Yankees, but we'll just focus on what we need to do."

A History of Ben Cherington and Brian Cashman

Cherington and the Yankees already have a rapport. In 2021, we saw the infamous Clay Holmes trade, where the Yankees sent Pittsburgh obscure prospects in Diego Castillo, once touted as a stolen base machine, and Hoy Park, who had a hot first half to his minor league season that year. Neither Park nor Castillo panned out, and Holmes proved to be a stabilizing force in the Yankees' pen for a time.

The most recent dealings between Cashman and Cherington occurred when he sent David Bednar to the Yankees in exchange for Rafael Flores, Edgleen Perez, and Brian Sanchez. It wasn't chump change since Flores was one of the better catching prospects in the Yankee farm, but it was still surprising to see an all-star closer with team control be moved for that prospect haul, while Tyler Rogers, a rental, seemed to command more for the New York Mets. He was traded for José Buttó, Blade Tidwell, and Drew Gilbert. On paper so far, a rental for the Mets costs more than a flame-throwing closer who will be with the Yankees for another year.

New York Yankees general manager Brian Cashman
Aug 23, 2023; Bronx, New York, USA; New York Yankees general manager Brian Cashman talks with the media before the game between the Yankees and the Washington Nationals at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

In the rare chance that Skenes is traded to the Yankees, the exchange would be huge. It's a wonder if the Yankees can even get a deal done once the league finds out Skenes is available. Just like the Dončić trade, it would have to be a situation where Cherington essentially shuts out every team in the league and doesn't field calls from the Los Angeles Dodgers, Milwaukee Brewers, or Seattle Mariners.

All of those teams were ahead of the Yankees in MLB Pipeline's mid-season rankings last season. Cherington might have to pull a Cherington and give the Yankees a discount, the way he did with Bednar, for anything even to happen.

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Published
Joseph Randazzo
JOSEPH RANDAZZO

Joe Randazzo is a reference librarian who lives on Long Island. When he’s not behind a desk offering assistance to his patrons, he writes about the Yankees for Yankees On SI. Follow him as @YankeeLibrarian on X and Instagram.