Every Pirates home game at PNC Park seemed to have a few things in common this season… A beautiful ballpark, a struggling clubhouse, and plenty of “Sell the team” banners waving in the stands. But did that bother team owner Bob Nutting? Apparently not. That indifference caught the attention of MLB insider Jeff Passan, who didn’t hold back. “It’s time for Bob Nutting to spend some money and give Pirates fans what they deserve.”

And his timing couldn’t be more fitting. Paul Skenes, basically the Pirates’ lone bright spot, is nearing his arbitration years. The team gets him at a bargain through 2026, but come 2027, things change. Hence, for Nutting, things are clear: if he doesn’t start investing now, the Pirates could be in for another long, painful stretch.

“On the first note, Bob Nutting has an obligation to navigate a public trust appropriately. If you can small-market your way to wins, cool. Other markets do. If you stink at that, you should act and change out regimes. Or if you need players, you should spend on them. And if you can’t do better than Tommy Pham when you have Paul Skenes, you should sell and give someone else a chance to try.” A page from the Pittsburgh Post-Gazette’s Jason Mackey offers dos and don’ts for Nutting.

Reportedly, Skenes is set for his first arbitration in 2027. And according to Spotrac, he’ll likely earn over $46 million across three years, through 2029. And once he hits free agency in 2030, projections suggest he could land a $40 million AAV. This means 2026 will be the last year the Pirates can keep Skenes at a bargain price.

But given Nutting’s history with payroll, it’s hard to feel optimistic about the Pirates investing big to keep him. The Pirates had the lowest payroll for years. For example, in 2025, the Pirates’ payroll was just under $90 million, the fourth-lowest in MLB.

Hence, as Mackey discusses, if Nutting doesn’t step up and invest in the team, it might be time for someone else to take charge. The Pirates haven’t had a winning season since 2018 and have been out of the postseason for nearly a decade. So, 2026 might be their last real shot at turning things around.

Skenes’ trading risk is looming for the Pirates

“The Yankees were one of only a handful of teams (fewer than five) that checked in on Paul Skenes even after word was out that the Pirates had no intention of trading the Cy Young leader,” MLB insider Jon Heyman said.

So, just when the Pirates are already strapped for cash, Skenes’s attracting attention from other cash-rich teams makes things even trickier for them. And it’s easy to see why… Skenes had a historic rookie season, posting the best ERA+ ever for a pitcher with at least 20 starts at 211. He threw 187.2 innings with a 1.97 ERA and a 0.95 WHIP, leading the league in all four categories. Moreover, he struck out nearly 30% of batters while walking just 5.7%.

But why are the Pirates still skeptical about offering a multi-year deal to Skenes?

Notably, the Pirates haven’t signed a free agent to a multi-year deal since Ivan Nova’s three-year, $26 million contract back in 2016. So, locking up Skenes could be their chance to start a culture shift in the organization. But with other teams circling, the window is closing fast.

Insiders say that if Nutting isn’t willing to step up and keep Skenes, maybe it’s time to let someone else take the reins and rebuild the team. The big question is… is he even listening?