Whenever a new star emerges in Major League Baseball, it’s almost a tradition to spread a rumor they would one day don dark blue pinstripes. As one of America’s premier sports teams and heavy spenders, the New York Yankees have accumulated a treasure trove of talent. Thus, any rumor of the Yankees expanding that pool of talent isn’t such a shot in the dark.

Do most of these unsubstantiated rumors come true? No, not really. Bryce Harper is with Philadelphia and Manny Machado is with San Diego, but we can’t always tell what general manager Brian Cashman has in mind. The Yankees have an ace in Gerrit Cole and had Juan Soto hitting ahead of Aaron Judge, albeit briefly.

Now, we are on to our latest edition of Yankee fantasies. This one involves the Pittsburgh Pirates’ uber-talented Rookie of the Year hurler Paul Skenes who has left a significant impression on the baseball world in just 23 games. Already, there have been some trade ideas and speculation that favors the Yankees, but that isn’t surprising.

But now, we have a new source fueling this Yankees-Skenes speculation; but with one big difference. This new source happens to be Brian Cashman himself.

Brian Cashman addresses a question on Paul Skenes with high praise and a back-story

It shouldn’t be surprising that Paul Skenes was on the Yankees’ radar before the 2023 draft. He was likely on every team’s radar. When asked by a reporter about his impression of Skenes, Cashman had this to say:

Brian Cashman was asked about his impression of Paul Skenes

"Jim Hendry (Yankees special assistant) saw him in the draft and told him he's the best starter he's seen amateur-wise in 10-20 years. Unfortunately we didn't lose enough games to be in a position to pull that one" 😂 pic.twitter.com/kk1q78tkYM

— Yankees Videos (@snyyankees) February 14, 2025

As Cashman pleasantly put it, “Unfortunately we didn’t lose enough games to be in a position to pull that one.” The Yankees were allotted the 26th pick of the first round during the June 2023 draft where they landed George Lombard Jr.

But given Cashman’s high praise, we can expect his radar has never deviated from Skenes. And given Pirates’ owner Bob Nutting’s low propensity to spend money, we can assume Skenes will be gone sooner or later.

The most lucrative deal in Pirates history is Bryan Reynolds’ extension priced at $106.75 million for eight years. Skenes will undoubtedly blow this figure away in free agency. Nutting knows this and may end up trading him further down the road.

While Cashman didn’t offer anything substantive on actually acquiring Skenes (it’s way too early for that), we can’t discount his typical stealthy motives. We’ve seen him zag when we expected him to zig. He wined and dined Machado before picking up DJ LeMahieu. Will the Yankees see a rotation featuring Gerrit Cole, Paul Skenes and Max Fried in the coming years? No one knows for sure, but Cashman may have given Yankees’ fans something to dream about. Because it’s just that, a dream.