BALTIMORE, MARYLAND – SEPTEMBER 10, 2025: Paul Skenes #30 of the Pittsburgh Pirates looks on during the sixth inning against the Baltimore Orioles at Oriole Park at Camden Yards on September 10, 2025 in Baltimore, Maryland. (Photo by Chris Bernacchi/Diamond Images via Getty Images)
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The New York Yankees are seen as one of the premier destinations in Major League Baseball, even if they haven’t captured a World Series championship in 16 years.
With a perennial top-tier payroll, the world’s largest media market and a passionate fanbase behind them, the Yankees still attract virtually any top-tier talent who wants to chase a World Series ring. And that has apparently motivated arguably the best pitcher on the planet to lobby for a trade that would send him to the Bronx.
“All-Star right-hander Paul Skenes, the 2024 NL Rookie of the Year and 2025 NL Cy Young favorite, has been telling Pirates teammates that he wants to play for the Yankees,” Randy Miller reported for NJ.com. “According to a 2024-25 Pirates player who recently spoke with NJ Advance Media, Skenes has ‘no confidence the Pirates ever are going to win’ with him in Pittsburgh, and he’s ‘hoping for a trade’ well before he can become a free agent after the 2029 season.”
On the surface, Skenes’ frustration would make sense. In his first two years in the majors, he has maintained a 1.96 ERA with 386 strikeouts in 55 total starts. His 1.97 ERA mark from this past season led all of the majors. He has twice been an All-Star.
But despite his individual success, the Pirates have languished and don’t seem to be willing to invest in building a competitive team around him. The team came in last place in the National League Central this past season with a 71-91 record.
Skenes faces several more years of team control before he would earn the chance to become a free agent and choose his destination, so advocating for a trade could be the only way for him to contribute to a more competitive season.
When asked about Skenes’ alleged comments, Pirates general manager Ben Cherington offered a blunt three-word response:
“I understand it,” Cherington said, per Miller.
“I have a ton of respect for the Yankees, but we’ll just focus on what we need to do,” the general manager added.
If Skenes’ reported lobbying motivates a trade, the return the Pirates will demand would be substantial. But as the superstar pitcher approaches free agency, the chances of such a deal are increasing.
“Trading Skenes somewhere down the road feels almost inevitable,” Steve Adams wrote for MLB Trade Rumors. “If he continues this trajectory, he’ll have the opportunity to shatter contract precedents for starting pitchers.”
With an outspoken desire to don pinstripes in the near future, perhaps Skenes will find himself traded to the Yankees before that free agency decision ever occurs.
