“I don’t know where that came from. The goal is to win, and the goal is to win in Pittsburgh.” Those were Paul Skenes’ words when rumors surfaced linking him to the Yankees. The 23-year-old made his commitment clear, but insiders are painting a different picture. While Skenes sees his future in Pittsburgh, those who watch the organization closely aren’t convinced the Pirates will give him a reason to stay.

The rumor mill has quieted for now, but this topic has become a hot topic among the analysts.

The conversation caught fire during a recent episode of JM Baseball’s podcast, where Chris Rose and Trevor Plouffe didn’t hold back. They started discussing how Paul Skenes made it clear he would stay with the ballclub. But they also think that if the front office doesn’t build around him, the trade will happen.

“You get a talent like this, a guy that, you know, one of the only pitchers that commands an audience the way he does every single start, like you’ve got to find a way to keep him,” Plouffe said.

His assessment was blunt: “Do I think he wins in Pittsburgh? I do not, which is sad.”

He acknowledged that the Pirates are building something special on the mound—they could have one of the best rotations in baseball if their young arms stay healthy.

But then came the gut-punch observation! “To have that at your fingertips, to have drafted and developed it, and to just like do nothing with it is sad. It’s sad for the city, it’s sad for your organization.” Plouffe didn’t see much hope for change either, suggesting it would probably require new ownership. His conclusion was definitive: “If nothing changes, he will not win in Pittsburgh.” “So I do think his time there is limited.”

The Pittsburgh Pirates have one of the lowest payrolls in baseball, with an Opening Day payroll of about $86 million in 2025.

Due to financial limitations, they struggled to build a deeper squad or support a strong rotation, making it difficult to retain talented players and compete effectively.

Paul Skenes has been open about his ultimate ambition, asking, “What else do I have to accomplish in this game?

A World Series championship.” That goal requires more than one exceptional pitcher. He’s also been clear about the front office’s promises, stating flatly, “Talk is cheap.”

Pirates GM Ben Cherington made it clear, “Skenes is going to be a Pirate in 2026,” but that only addresses next year.

Plouffe’s take on the podcast went further, suggesting meaningful change might require new ownership entirely, which speaks to how deep the organizational issues run.

The front office must act soon. He might not be going anywhere this winter, but the next? That depends entirely on whether the Pirates commit to building a winning team. Because Skenes is doing everything, and he just earned the ultimate validation for his 2025 performance.

CY Young Excellence

The 23-year-old just became the third Pirate in franchise history to win the Cy Young Award, joining legends Vern Law (1960) and Doug Drabek (1990). His unanimous selection wasn’t just deserved—it was inevitable after one of the most dominant pitching seasons the organization has ever seen.

Paul Skenes posted a 10-10 record with a 1.97 ERA across 32 starts and 187.2 innings.

He struck out 216 batters—setting a franchise record for strikeouts by a right-handed pitcher—and posted a 5.14 strikeout-to-walk ratio, the best in team history.

He has been the most consistent arm not only in the clubhouse but in the league, too.

Yet the Pirates were eliminated from playoff contention by mid-season, watching from the sidelines while their ace dominated.

That 10-10 record tells you everything about the lack of run support he received. In his 10 losses, the Pirates’ offense gave him just 11 runs total. A Cy Young winner finishing .500 isn’t a reflection of his performance—it’s an indictment of everything around him.

The window for keeping a talent like this doesn’t stay open forever, and Pittsburgh’s track record suggests they know how this story usually ends.

We have seen how Gerrit Cole, Glasnow, Clay Holmes, and many more developed with other clubs, and their skills did not go to waste. Can Paul Skenes be next in that list?