The New York Yankees remain firmly connected to Paul Skenes, the 2025 National League Cy Young Award winner, as his future free agency approaches. Discussions have intensified due to both Skenes’ growing prominence as a premier pitcher and his girlfriend Olivia Dunne’s ties to New York City. Although Skenes is under contract with the Pittsburgh Pirates through 2029, when he hits free agency, major teams like the Yankees are expected to show strong interest.
MLB insider Julian Guilarte explained why the Yankees could be prime candidates for signing Skenes. He noted that by the time Skenes reaches free agency, the Yankees’ payroll will be largely cleared of commitments except for Max Fried, leaving financial room to pursue elite talent. Guilarte also emphasized Skenes’ desire to join the Yankees, stating,
“He definitely wants to be a Yankee, I don’t even need to know that.”
Co-host Keith McPherson highlighted Olivia Dunne’s preference to remain in New York, pointing out her recent purchase of a Manhattan home after unsuccessfully attempting to buy Babe Ruth’s former apartment. This personal connection may further influence Skenes’ potential move.
Guilarte dismissed the New York Mets as a likely destination, citing concerns about salary cap limitations and the team’s current payroll, while also ruling out the Los Angeles Dodgers, suggesting Skenes would prefer not to move westward. He remarked,
“If there’s no salary cap, I don’t think there’s a number, whether we’re looking at four or five, it’s going to be something ridiculous.”
Pittsburgh Pirates Firm on Keeping Skenes for Now
The Pittsburgh Pirates, typically not consistent postseason contenders, often face trading key players to rebuild. However, Paul Skenes appears to be an exception amid trade rumors. Pirates General Manager Ben Cherington has made it clear that Skenes will remain with Pittsburgh for the 2026 season, showing the organization’s intent to hold onto their star pitcher through most of his current contract.
This firm stance reduces the likelihood of a trade in the immediate future, as the Pirates recognize Skenes’ rising status and value. Cherington’s comments underline Pittsburgh’s plan to develop around Skenes at least until his contract nears its end.
Financial Considerations and Market Dynamics Surrounding Skenes
The evolving landscape of Major League Baseball’s salary structures plays a significant role in the anticipated free agency of Paul Skenes. The Yankees’ impending payroll flexibility means they will be among the few teams capable of committing large sums required to sign star pitchers like Skenes once his contract expires.
Julian Guilarte explained how the departure of high-profile contracts will free up space, allowing the Yankees to offer competitive deals without conflicting with upcoming salary cap measures. This financial openness stands in contrast to teams like the Mets, who face budget constraints.
At the same time, the direction of Skenes’ decision seems influenced by off-the-field factors, particularly his personal ties to New York through Olivia Dunne, whose social media presence and affinity for the city add another layer to the Yankees’ appeal.
Broader Implications for the League and Future Prospects
Securing Paul Skenes would significantly bolster the Yankees’ pitching roster, potentially shifting the balance of power in the American League. As Skenes is a dominant flamethrower with Cy Young credentials, his arrival could elevate the Yankees’ postseason competitiveness in the coming years.
The Pirates’ current plan to retain him through 2026 suggests a window for Pittsburgh to build more supporting talent before facing the possibility of losing him to free agency. Should the Yankees succeed in landing Skenes, it would mark a strategic acquisition aligning with both their financial readiness and the player’s preferences.
This anticipated move also signals the increasingly interconnected nature of personal, financial, and competitive factors influencing player decisions, where star athletes weigh organizational fit alongside family and lifestyle considerations.
Talked about the Yankees getting Paul Skenes around the time his free agency comes with @Keith_McPherson and why we think it’s realistic possibly.
Shoutout to @_BigSteve89 for starting the conversation.
Click the link for the full video: https://t.co/Vy2JQW2IUp pic.twitter.com/ACWlD9DBGM
— Julian Guilarte (@JulianGuilarte1) February 6, 2026
