Another season has slipped through Pittsburgh’s fingers, and another year of Paul Skenes’ great play spent on a team going nowhere. The Pirates’ payroll stood at 27th in MLB in 2025, and the whisper of extending their ace is getting louder. Bob Nutting is at a crossroads. So, one sports analyst just gave him a plan that doesn’t cost a lot of money but does require something Pittsburgh has been missing for years: A sense of urgency.

The Toronto Blue Jays are where the plan comes from. Emma Lingan put it plainly in her recent column. “The Pirates’ front office hides behind “budget restrictions,” but the Blue Jays showed that urgency is free. They didn’t win because of payroll; they won because they played like a team with something to prove after finishing last. They spent modestly but strategically and traded from surplus instead of waiting for perfect timing.”

This past offseason, Toronto made a choice that changed everything.

They gave Vladimir Guerrero Jr. a 14-year, $500M deal and then surrounded him with players that suit certain needs instead of trying to get headlines. On paper, the choices weren’t up to the mark, though.

With Anthony Santander and Gimenez struggling, Max Scherzer had a poor ERA, and Jeff Hoffman blew seven saves. Bo Bichette’s knee injury in early September didn’t help either. Still, the Jays kept winning. Credits? Toronto’s smart signs of players like Santander, Hoffman, and a bullpen that was on point.

Santander came with his defensive and switch-hitting skills. For second base stabilization, there was Gimenez. And as Lingan put it, “Hoffman and Scherzer soaked up innings and experience, even if inefficiently.” It has been “role-specific” names around Vladdy over splashy million-dollar deals that have brought them so far.

As per Lingan’s observations, Pittsburgh needs to do the same thing with Skenes. And Bleacher Report’s Zachary Rymer had some idea about how.

“…hope that he’ll [Nutting] make some kind of effort to put a winning team around Skenes while he has the chance. And right now, that means adding bats. First base and DH were the only positions that didn’t produce a sub-.700 OPS this year, so any upgrades should be on the table. They might succeed by offering full-time work to platoon hitters, such as Amed Rosario or Dylan Moore.”

So, if the Pirates give him an extension now, it will show fans, players, and the league that they are not just accumulating prospects anymore. They’re making something that will last. The Pirates won’t need luck on their side if they follow Toronto’s blueprint: Stabilize the team with reliable players, and put money into growing better.

Paul Skenes is the most important player on this team. It’s hard to see Pirates without him.

Jon Heyman even pointed out that it looks like the Pirates front office would “likely extend” the All-Star, but it’s not clear how or when. Now, Nutting has to choose because time is running out.

And Emma Lingan isn’t the only one who recognized that the Pittsburgh front office is stuck and needs to work on its blueprint.

Passan’s wake-up call to Pittsburgh

As Toronto’s method continues to be a model for small-market success, analysts are focusing on Pittsburgh’s unwillingness to act. ESPN insider Jeff Passan recently talked about how Bob Nutting dealt with the Paul Skenes case, pointing out what could eventually be one of MLB’s worst missed chances.

When Passan talked about the problem, he didn’t hold back. “The Pittsburgh Pirates are three bats away from being a playoff team right now, and the only way they’re going to get those bats is if their owner spends some freaking money. And if not now, then when? At what point do you see this talent and say, ‘We need to take this opportunity and give fans what they deserve.'”

Paul Skenes’ 2025 season has been nothing short of amazing.

The right-hander had a 1.97 ERA and 216 strikeouts in 187.2 innings. He frequently dominated lineups with a blend of command and power that is unique for pitchers his age. Those stats put him well in the running for the Cy Young Award, which would make him the first Pirate to win it since Doug Drabek in 1990. His emergence has changed the rotation and given the team its first real ace in decades.

What makes Pittsburgh’s hesitation even more puzzling is that Paul Skenes is doing this while earning just $800,000 on his rookie contract. He won’t be a free agent until 2030, so the Pirates have five years to keep him for a fraction of the market value. And if he hits the free market, every clubhouse in the league will run after him.