For the Pittsburgh Pirates faithful, this is a story that has become all too familiar. They find a rare, once-in-a-generation talent, watch him dominate, and then in the background, the clock starts ticking. In 2025, that talent is Paul Skenes. Despite the team’s poor 38-56 record, Skenes has been outstanding on the mound, posting a 1.94 ERA. His remarkable performance, however, brings to mind Gerrit Cole, whom the Pirates had to trade away at the peak of his career.

And this feeling of impending doom isn’t solely fan anxiety. A well-known insider from Pittsburgh has earmarked a specific time frame for the inevitable. In the Pirates mailbag on the Pittsburgh Post-Gazette, renowned journalist Noah Hiles made a bold forecast. While responding to the question whether 2026 could be Skenes’s last season with the team, he offered his thoughts without holding back.

“If I had to make a bet right now, I think 2026 will be Skenes’ final full year in Pittsburgh,” Hiles said. Now, this is a chilling assessment. Hiles, however, explained the cold logic behind it. This goes beyond money; it’s about winning. Skenes is a competitor who wants a ring.

“Skenes wants to play for a winner. He’s not signing an extension with this team if they’re not a legitimate threat to compete in the postseason,” Hiles elaborated. Continuing further, he added, “And if they’re not playing to that level after 2027, then it would be in their best interest to trade him anyway.”  The franchise is at a pivotal point: create a championship-caliber team or abandon ship and lose the valuable trade chip.

The heart of the issue is maximizing the value of the player. It might be a tough pill to swallow for the fans, but each season that goes by brings Skenes closer to free agency, which in turn drops his trade value. “Skenes’ trade value lessens every year he remains a Pirate,” Hiles noted, before adding, “Unless you truly believe he can help you win a World Series in 2028, he should be moved after the 2027 season.”

This is a tough go, but it may bring in a large return of prospects to a team that is very much in need of building for the future. For the front office, it’s a brutal calculation. Trading a beloved superstar is a public relations nightmare. However, the potential return could reshape the franchise for years to come. “The return for Skenes with multiple years of control will be much better for the Pirates’ long-term future,” Hiles concluded.

As insiders map possible departures, those central to any action, understandably, are moving quickly to calm the noise.

Unpacking the inevitability: What the key characters are saying

The Pirates’ GM Ben Cherington has all but laughed at the idea of trading his young ace right now. When asked about it, he issued a clear, definitive no: a trade was “not part of the conversation at all.”

Paul Skenes himself has handled the speculation with a veteran’s poise. He is mindful of the business of baseball but is concentrating on his job. “Ben’s job is to create a winning team and a winning organization,” he said thoughtfully. “If he feels (trading me) is the right way to go, then he feels that’s the right way to go.”

However, Skenes also issued a challenge to himself, adding, “I think we owe something to the city… The fact that that’s [the 2013-15 teams] a golden era of recent Pirates baseball, that needs to change.”

Well, we can’t ignore the glaring hole in the Pirates’ lineup. Even Cherington admits where the problem lies, stating, “We do feel pressure to create more offense, for sure.” That pressure is grounded in statistical reality. The 2025 Pirates have had one of the worst offenses in baseball. They rank 30th in both home runs (64) and slugging percentage (340), and 29th in runs (319). Key contributors such as Bryan Reynolds (227 AVG) and Ke’Bryan Hayes (.241 AVG, 2 HR) have disappointed, with Oneil Cruz (16 HR) providing the only consistent power threat.

It puts Pirates fans in an awkward spot. Do they root for the team to trade valuable players now to construct around Skenes, or do they leave it to the ownership to decide when to spend? Let us know what you think the Pirates should do.