Paul Skenes won't be a free agent until 2029, but because he plays for the Pittsburgh Pirates – a small-market team which is seemingly always shopping its stars – he's already been floated in trade talks by pundits and rival executives alike. The Yankees, unsurprisingly, have been a popular destination.
For what it's worth, Pirates president of baseball operations Ben Cherington has maintained the team is not shopping Skenes, but rather intends to build around him. That makes sense: Skenes was drafted No. 1 overall just over two years ago; he's only 23 years old, won the NL Rookie of the Year award in 2024 and could take home the NL Cy Young later this week.
If the Pirates were to trade Skenes, they'd receive a litany of top prospects they'd hope to develop into ... the next Skenes. Since he's under team control for the next half-decade, any deal – whether it be to the Yankees or elsewhere – is highly unlikely. Thus, floating Skenes to the Yankees, Dodgers Angels or any other team is little more than a thought exercise right now. But that won't stop the New York media from manifesting trade rumors whenever they have the chance.
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Does Paul Skenes already have an eye on the Yankees?
One of Skenes' teammates from the past two seasons (2024-25) reportedly told NJ Advanced Media that the righty has little confidence in the direction of the Pirates organization and is hoping to be traded well before he reaches free agency in the 2029-30 offseason.
“Trust me, he wants to play for the Yankees,” the Skenes teammate said. “I’ve heard him say it multiple times.”
NJ.com's Randy Miller did his due diligence on this report, asking Ben Cherington about the possibility of a Skenes trade to the Yankees.
“I do dismiss it, but I understand it,” the Pirates executive said. “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.”
Again, Cherington has little reason to be worried of losing Skenes right now. He's under contract through the 2029 season and hasn't yet voiced his desire to be traded.
“In a nice way, it’s really simple because what matters most to (Skenes) is what matters to us,” Cherington said. “Win more games. That’s the focus because that’s what is going to be most important to him. What probably gives us the best chance to keep him in Pittsburgh for longer is winning games, and that’s what we need to do anyway."
The good news for the Pirates is that Skenes isn't going anywhere for now. The bad news is that these conversations will continue for as long as Pittsburgh falls short of expectations, and this is a team that finished in last place in the NL Central last season. Until the Pirates make the postseason on a regular basis, and Bob Nutting proves willing to spend the money necessary to reach that goal, Skenes' name will be floated in trade rumors. That's how this business works.
So, which Pirates teammate linked Paul Skenes and the Yankees?
When narrowing down which former or current Pirates teammate snitched to Miller, one first has to look at which players spent time in both organizations, or are outspoken enough to reveal Skenes' long-term plans to the media. Given how the Pirates' season ended – and the outspoken nature of several Pirates stars in the aftermath – it could feasibly be anyone.
Andrew McCutchen
However, per my best guess, I've narrowed it down to three players. The first, who has the highest profile of any current Pirates players, is Andrew McCutchen, who voiced his displeasure with the Pittsburgh front office at the end of the season.
“I feel like we're beating the same drum,” McCutchen told the Post-Gazette. “Third year back, kind of feels the same just from an instance of where we are. It does kind of feel the same. And from that, in that instance, just looking at where have we improved, or where do we need to get better? And kind of feels the same, same answers that you have internally. Yeah, it just leads me to think, like, what's the plan moving forward, and what is it gonna look like next season?”
However, despite what McCutchen said a little over a month ago, he's shown a surprising amount of loyalty to the organization that drafted him. It's tough to believe he'd blow it up, even anonymously.
What about Isiah Kiner-Falefa or Tommy Pham?
Another popular candidate is Isiah Kiner-Falefa, who spent the 2024 and part of the 2025 season with the Pirates and is himself a former Yankee. It wouldn't be a surprise if he still had some ties to New York or a relationship with Miller. And as a former Pirate, he'd have a far easier time speaking out against the team and thus putting Skenes in the spotlight.
Among players on the current team, I'd pinpoint Tommy Pham as someone who, despite performing well in Pittsburgh, is outspoken enough to talk to the media on Skenes' behalf. Pham is a popular target to return to the Pirates in 2026 should they meet his free-agent asking price, as he had a .700 OPS and 95 OPS+ this yera. Those aren't tremendous numbers, but Pham was a much-respected clubhouse veteran.
Pham is also the same player who's been involved in on-field skirmishes and once even slapped Joc Pederson over a fantasy football dispute. Were he to speak against the Pirates in this case, the betrayal would be metaphorical but enormous.