Paul Skenes’s first season with Pittsburgh was historic. But when no one is watching, the 2024 Rookie of the Year and likely 2025 Cy Young winner is telling his teammates something terrible.

One undisclosed Pirates player reportedly revealed to NJ Advance Media that Skenes has made it clear that he wants to leave Pittsburgh. The 23-year-old from California has told his teammates that he “has no confidence the Pirates ever are going to win” with him in the organization. He is “hoping for a trade” well before his free agency eligibility after the 2029 season.

This feeling is strong because the Pirates have only had four winning seasons and three playoff appearances since Barry Bonds left as a free agent in 1992. They finished last in the NL Central both years Skenes has been with the team, with records of 76-86 in 2024 and 71-91 in 2025. The difference is apparent.

Skenes had a record-breaking 1.97 ERA and 216 strikeouts last year, but even his greatness couldn’t stop the team from falling apart.

Skenes used to be a fan of the Los Angeles Angels, where he grew up idolizing Mike Trout. But now, he is a fan of the Yankees. New York has annual contention and unlimited money, unlike Pittsburgh and Anaheim. The teammate reportedly made the point very clear.

“He wants to play for the Yankees. I’ve heard him say it multiple times.” The Yankees are everything the Pirates can’t be: stable, able to spend money, and a culture of winning. The New York Yankees had 94 wins in 2025. So, Paul Skene’s choice may be based on a basic calculation.

Skenes knows that Pittsburgh’s recent history has been marked by organizational poverty, as they have been one of the lowest-spending teams in baseball for 16 of the last 19 seasons.

When confronted with these rumors at baseball’s General Managers Meetings, Ben Cherington acknowledged the situation’s complexity.

“I do dismiss it, but I understand it,” he said. Rather than deny the player’s frustration, he framed the relationship pragmatically. “What matters most to him is what matters to us—win more games. That’s the focus.”

Cherington said that Skenes will still be a Pirate in 2026, showing that the organization is determined. But his method shows the hard truth: keeping players depends only on winning, not on promises. Cherington has a tough job ahead of him to turn commitment into results, since ownership has promised only small pay raises from last year’s $87.6 million, which ranked 27th out of 30 clubs.

Cherington says publicly that he will keep Skenes and build a winner, but the Pirates’ real actions tell a different story.

Mitch Keller becomes collateral damage as the Pirates prioritize cutting costs

The catch is that Cherington tells Skenes that the Pittsburgh Pirates are committed, but the front office is quietly shopping starter Mitch Keller to save money. This isn’t just a coincidence.

This is the clearest sign yet that Pittsburgh is choosing money over winning, which is exactly what Skenes has been telling his teammates.

Keller joined the Pirates in 2019 with a lot of potential as a pitcher. His record tells the real story: 42 wins and 65 losses in 163 starts, with a 4.19 ERA and 837 strikeouts. He hasn’t always been consistent, but the main issue is his contract.

He signed a five-year, $77 million extension last February that requires payments of $15.9 million, $18.4 million, and $20.4 million over the next three seasons.

The Pirates can’t afford the bill. So they’re exploring trades.

“You can’t have Paul Skenes, but Mitch Keller is more than available,” one insider revealed, referring to recent talks with the Chicago Cubs. The message is unmistakable: protect the young superstar publicly, dump everyone else privately.

“He still has three more years on his deal with those millions owed. And the Pirates love nothing more than saving money,” another observer noted.

That’s the issue. Skenes sees that Cherington’s promises don’t mean anything and that ownership cuts costs instead of putting money into winners. The Pirates aren’t building around him; they’re taking things apart around him.