Pirates ace Paul Skenes is a virtual lock to win the National League Cy Young Award on Wednesday, with betting markets pointing to a more than 99% implied probability of his prevailing. The chances of Skenes remaining in Pittsburgh for the duration of the career are less certain.
Ben Cherington, the team’s GM, reiterated at Major League Baseball GM meetings in Las Vegas that he has no intention of trading his standout talent.
“The question gets asked, and it’s always respectful,” Cherington said. “Teams have to ask the question, right? I suspect that won’t end. But the answer’s been consistent.”
To his point, the latest comments mirror those from last spring, when Cherington said of dealing Skenes in the midst of another lackluster Pirates season, “It’s not at all part of the conversation.”
Losing, Not Spending
The calls for the Pirates to do much more around Skenes, however, are certain to continue. Pittsburgh has posted seven straight losing seasons, has finished in the NL Central division cellar the last two years, and in 2025 had MLB’s No. 27 luxury-tax payroll of $105.4 million—barely a fourth of what the Dodgers spent this year.
Additionally, it’s teams like Pittsburgh—ones that are seen as not necessarily maximizing their resources—that are frequently viewed within baseball as a bigger problem in the game than the Dodgers, back-to-back league champions through unprecedented levels of spending.
Pinstripe Chatter
As Cherington repeated his intent to keep Skenes in Pittsburgh, NJ.com reported that Skenes is privately telling his teammates that he wants to be a Yankee and that he has “no confidence” that the Pirates and owner Bob Nutting will develop a winner. Cherington rejected the notion.
“I do dismiss it, but I understand it,” Cherington said. “What we’re going to focus on is just how do we win games with him in a Pirates uniform.”
Skenes, who earned $875,000 this season, is eligible for salary arbitration after next season and for free agency after the 2029 season.
Any consideration of dealing Skenes would be a double-edged sword for the Pirates. Sending away someone who is already one of the top players in franchise history would be a particularly tough blow for a long-pessimistic fan base in Pittsburgh. Any return for Skenes, however, would be massive and could be baseball’s equivalent of the NFL’s Herschel Walker trade, a 1989 deal between Minnesota and Dallas that helped set up the Cowboys’ dynasty in the 1990s.
