As Paul Skenes pitched his way into history this summer, fans and media wondered not if but when the team would trade him. Rumors grew so strong that a team executive insisted there was “no way, no chance, no how” Skenes was moving. GM Ben Cherington echoed that, saying the Pirates “can and will play better.” Yet after back-to-back disappointing seasons, those words did little to calm Pittsburgh’s unease. Burned by history, Pirates fans just watched the calendar, bracing for the inevitable.

But a new report from the GM meetings in Las Vegas gives some hope. The dream of keeping Paul Skenes in Pittsburgh is not dead yet. MLB insider Ken Rosenthal reported that the Pirates and Marlins are signaling a new strategy, suggesting owner Bob Nutting might finally open his wallet. “But what would be more intriguing would be if we saw teams like, for instance, the Marlins and the Pirates do some things to better themselves by trading from their depth of prospects. And I do believe that is possible.” Rosenthal said on the Foul Territory show.

“Yesterday, in talking to some people here—just the first day of the GM meetings, actually, it wasn’t even the first day, people were just getting in—I heard that the Marlins and Pirates are telling agents, ‘Hey, we’d like to be aggressive. We want to spend a little bit.” Now, that can be in free agency, or it can be in the matter of taking on salaries in trades.”

Pirates GM Ben Cherington also confirmed they have more flexibility than ever. And they are planning to explore new trades and free agents to upgrade the team alongside Skenes, as per Robert Murray of Fansided.

This new attitude comes when the team has already crossed the critical patience line. They finished the 2025 season with a 71-91 record, the tenth consecutive year the Pirates missed the playoffs, and they have only one winning season during this tenure.

The only bright spot in that darkness was Paul Skenes. He was arguably the best pitcher in baseball in his back-to-back Cy Young-caliber campaign.

And another good thing is Skenes is under contract through the 2029 season.  And he will be affordable through arbitration for quite some time.

Plus, the Pirates’ pitching staff is impressive and ranked seventh in all of MLB in ERA last season. So, the problem is simple: they cannot hit. And the numbers back that.

They scored the fewest runs (583), fewest home runs (117), and their offense was dreadful. If Nutting actually spends on a few bats, this team could compete immediately.

This all sounds perfect, but the Pirates fans have heard this song before

It is hard to trust an organization that is notorious for refusing to spend money. The owner, Bob Nutting, is infamously cheap and has his own track record. The Pirates’ payroll is always near the bottom of the league. In 2023, they ranked 29th. In 2024, they ranked 29th again with just $87.3 million. And last season it dropped to $85.5 million, ranking 26th overall in all of baseball.

And let’s look at the “big” moves. The last multi-year free agent deal the Pirates signed was Ivan Nova’s three-year, $26 million contract. It was in 2016. And the largest free-agent deal in the Pirates franchise history is still Francisco Liriano’s three-year $39 million contract in 2015.

So let’s live in a “perfect world” for a minute. If we believe Nutting and Rosenthal, what does “aggressive” actually mean? It does not mean signing top-tier free agents. They will not go and sign Pete Alonso or Alex Bregman in free agency.  Any contract over $13 million per year would break their franchise record, and that is not going to happen.

The most plausible scenario is reallocation. The Pirates are reportedly shopping All-Star pitcher Mitch Keller, who is owed $16.5 million in 2026. Trading him would free up that cash. That move would nearly double Cherington’s functional budget from $22 million to $38 million.

The other paths are less exciting. They might sign power-hitter Eugenio Suarez for third base or Rhys Hoskins. The other option is the “salary dump.” The Pirates could “buy” prospects by taking on a bad contract, like Nolan Arenado’s. 

And while Rosenthal’s national report sounds nice, Noah Hiles of the Pittsburgh Post-Gazette dropped some cold water on the rumors. Hiles said he does “not expect payroll to be much higher, if at all. I wouldn’t even be shocked if it was lower on opening day.” Why? Hiles reported, “Revenue wasn’t what they thought it would be in 2025, and this owner isn’t spending more to fix it.” This is the reality.