Alexander Wilson
Brian Cashman tried. He always tries. That is what you do when you run a franchise built to win now and the best 23-year-old pitcher on the planet is sitting in Pittsburgh posting a 1.97 ERA.
Jon Heyman of the New York Post reported late on Thursday night that the New York Yankees made a run at Paul Skenes last July and got exactly the response anyone with a pulse could have predicted. “The Yankees, perhaps encouraged by their belief Pirates superstar Paul Skenes might have interest in them (true or not), tried for Skenes at the deadline but were shut down so quickly the Pirates didn’t even listen to the offer, sources say,” Heyman wrote.
Not countered. Not declined after consideration. Did not even listen.
What New York Was Willing to Give Up
The audacity of the offer was real. According to Heyman, the Yankees were prepared to put together a package of four top prospects, a haul that reportedly could have included Cam Schlittler. Let that sit for a moment. Schlittler is now a legitimate piece of their Opening Day rotation, a 26-year-old arm who just put together one of the more encouraging springs in the organization and positioned himself as a potential mid-rotation anchor for years to come. The fact that Cashman was willing to include him in a Skenes conversation tells you everything about how the front office values the Pirates ace.
The Yankees also reportedly had Spencer Jones and George Lombard Jr. in conversations at various points. Jones is their top outfield prospect. Lombard is the organization’s top overall prospect and would be a Gold Glove defender on Day 1. The willingness to put those names on the table is not a casual gesture. That is an organization saying out loud that they would rather have four years of Paul Skenes than the next decade of their best young players combined.
Pittsburgh never flinched. Their general manager Ben Cherington had been saying the same thing for months. “The question gets asked, and it’s always respectful,” Cherington said at the GM meetings last fall. “Teams have to ask the question. I suspect that won’t end. But the answer’s been consistent.”
Why Pittsburgh Is Not Moving
It would be easy to frame the Pirates’ refusal as organizational stubbornness, but the math genuinely does not work in the Yankees’ favor right now. Skenes does not reach free agency until after the 2029 season. He is 23 years old and coming off a season in which he took home all 30 first-place NL Cy Young votes, posting a 1.97 ERA across 187.2 innings with a 0.95 WHIP. His career ERA across 55 starts is 1.97. That is not a good pitcher. That is a generational one, arguably the best arm in baseball right now, and the Pirates have him under team control for four more seasons at a fraction of what he will eventually command on the open market.
When the day comes that Skenes hits free agency, the projection floated in Heyman’s piece is roughly $50 million per year under the current rules. For context, Max Fried signed with the Yankees for just under $27 million annually. Skenes is about to become the most expensive pitcher in the history of the sport, and Pittsburgh holds all the leverage until 2030.
Skenes himself shot down the anonymous teammate report that suggested he wanted out of Pittsburgh. “It’s not true,” he told reporters in December, addressing the suggestion that he had privately expressed a desire to play for the Yankees.
What the Yankees Do Now
Heyman’s piece makes clear that Cashman has not stopped dreaming. “Expect the Yankees to circle back if they ever detect even a glimmer of an opening,” he wrote. Part of that hope, rightly or wrongly, stems from Skenes’ girlfriend Livvy Dunne living in New York. It is a thin reed to hang a trade pursuit on, but it is also the kind of soft intelligence that keeps front office phones active in October.
The more realistic path is time. If the Pirates cycle through another losing season and Skenes remains under contract without any extension progress, the organizational calculus could eventually shift. Cherington will not trade him on a team-friendly deal, but a Skenes who has made clear he will not sign long-term in Pittsburgh becomes a very different asset than a Skenes who might stay forever.
I think the Yankees get another run at this before he reaches free agency. Whether Pittsburgh listens that time is a different question entirely.
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