Last Updated on May 16, 2025 by Matt Musico
The New York Yankees enter play on May 16 comfortably atop the American League East with a 25-18 record and a four-game lead. But as the trade deadline creeps closer, general manager Brian Cashman will be looking for ways to bolster the roster so they can make another run to the World Series.
Could Pittsburgh Pirates ace Paul Skenes be a legitimate target? After all, the 2023 top overall pick has only just reached one full calendar year in the big leagues, accumulating 187.2 dominant innings in the process.
He plays for the Pirates, though, so anything is possible at this point, right?
It doesn’t seem like Pittsburgh is going to be competitive at any point soon. While they have some intriguing young talent, ownership and the front office haven’t invested enough in the roster via external acquisitions to make a serious run in the National League Central.
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ESPN’s Jeff Passan recently said that contending teams will ask about Skenes ahead of the trade deadline. He also noted that it might be the Pirates’ “best course of action” because any deal involving the righty would include an absolute haul in return for the organization.
Jeff Passan says the Pirates' best course of action might be to trade Paul Skenes and that teams will ask about him at the trade deadline this year.
We haven't even had him for a full season yet. pic.twitter.com/EIsIJqyLkO
— Dom DiTommaso (@DomDiTommaso) May 14, 2025
Any trade including Skenes right now seems far-fetched, but how ridiculous is it to think the Yankees could be a legitimate landing spot? Pinstripe Nation’s Esteban Quiñones feels like it could happen.
“The New York Yankees’ perpetual hunt for elite pitching has found a new fixation: Paul Skenes,” Quiñones wrote. “As Pittsburgh’s organization spirals into another rebuilding cycle, whispers about the future of their generational talent grow louder, with Yankees supporters leading the speculation chorus.”
Outside of the obvious deep price the Yankees would have to pay in prospects to land Skenes, it would eventually cost them a lot of actual money to retain him. The righty has posted a 14-7 record with a 2.16 ERA, 0.96 WHIP, and 223 strikeouts since debuting last season. However, the immediate financial cost wouldn’t be terrible – he’s making just $875K in 2025 and isn’t eligible for arbitration until 2027, per Spotrac.
But when it comes time to pay the man, Passan thinks what Skenes brings to the table could make him “baseball’s first half billion-dollar pitcher.”
And just for some perspective, the current richest contract for a pitcher in baseball history is Yoshinobu Yamamoto’s 12-year, $325 million deal with the Los Angeles Dodgers.
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