On Wednesday, a report from NJ Advanced Media's Randy Miller quoted one of Paul Skenes former teammates, arguing that the current Pirates ace and 2025 NL Cy Young winner wants to play for the Yankees. Skenes denied that report when interviewed following his decisive Cy Young victory, but don't expect the chatter to end anytime soon.
Skenes is just 23 years old and under contract with the Pirates through the 2029 season. Ben Cherington already said the team won't consider trading him this winter, while Skenes made it clear on Wednesday night that he wants to win in Pittsburgh. But this is New York we're talking about. The Yankees run the town, and Mets owner Steve Cohen is the richest owner in baseball. Thus, Skenes will be connected to the Big Apple until he signs a long-term contract in Pittsburgh or elsewhere.
Enter the New York media landscape, which is fueled by tabloids and rumors.
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Paul Skenes girlfriend, Olivia Dunne, bought an apartment in New York
Olivia Dunne is a social media influencer and former LSU gymnast. She's been dating Skenes for a few years, and but no means tied to his hip. These two live very independent lives, supporting each other every step of the way.
However, when Skenes' partner signed a lease in Manhattan's lower west side, the Post took note. New York Magazine even wrote a feature on Dunne's new apartment and life in lower Manhattan.
Now, what does Dunne's affinity for New York have to do with Skenes? Naturally, nothing. Both Dunne and Skenes made more than enough money to live in multiple locations, with Skenes spending time each offseason in Pittsburgh, Louisiana and, now, New York. That's just fine! Manhattan is a great vacation spot. It also doesn't mean Skenes is going to be a Yankee.

What Paul Skenes said about his future in Pittsburgh speaks volumes
In this day and age, we have to take athletes at their word, especially when one is as young as Skenes. He has little control as to where he plays baseball for the foreseeable future. His best chance at increasing his free-agent value (or extension value, if Pittsburgh is lucky) is to maintain his star status and lead the Pirates to the postseason. That's unlikely to happen in 2026, but if the Pirates front office is to be believed, they are committed to spending more on player payroll this winter.
"I don't know where that (report) came from," Skenes told reporters Wednesday night. "The goal is to win, and the goal is to win in Pittsburgh."
"The way that fans see us outside of Pittsburgh, Pittsburgh is not supposed to win," Skenes continued. "There are 29 fan bases that expect us to lose. I want to be a part of the 26 guys that change that."
Any trade for Skenes would require a king's ransom in return, and the Pirates would just be trying to acquire another player of his caliber, but younger and with far less certainty. The best path forward for Pittsburgh is to build a contender from within, led by Skenes and No. 1 prospect Konnor Griffin, who could reach the majors as soon as next season.
Of course, actually taking advantage of that contention will depend on Bob Nutting and Pirates ownership. Pittsburgh is never going to spend as much money as the Yankees or Mets, but if they hope to keep Skenes from ACTUALLY seeking a path to New York, their best chance is to prove him what a well-run small market team has to offer.
