Year after year, the conversation around the Pirates’ shrinking payroll feels like deja vu, frustratingly familiar and endlessly disheartening. Despite boasting some of the most electric young talent in baseball, a fanbase that continues to show up in the stands, and arguably the most picturesque ballpark in all of MLB, the Pirates have yet to capitalize on their potential. And the dry spell is glaring. No postseason appearance since 2015, and a World Series drought dating back to 1979.
The root of the problem? A persistent unwillingness to spend. Well, it’s become such a glaring issue that even MLB Commissioner Rob Manfred has taken public notice. Now, with potential league intervention on the horizon and rumors swirling about the team prioritizing the retention of generational pitcher Paul Skenes, hope flickers once more in Pittsburgh. Especially after GM Ben Cherington’s recent comments hinted at a more aggressive approach for 2026.
But wait…When it comes to the Pirates, hope often feels like a trap. And just as fans began to entertain dreams of a true turnaround, a new report has surfaced, casting doubt and signaling that, once again, expectations may prove to be a costly mistake.
“Pittsburgh Pirates general manager Ben Cherington said last week that the money the team saved at the MLB trade deadline would be reallocated. It appears that money will not be reallocated into a larger budget in 2026. Two sources briefed on the situation told Pittsburgh Baseball Now that owner Bob Nutting will likely give Cherington the same player payroll as this season or perhaps a bit lower,” wrote columnist John Perrotto in his latest column for Pittsburgh Baseball Now.
MLB, Baseball Herren, USA Cleveland Guardians at Pittsburgh Pirates Apr 19, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington observes batting practice before the game against the Cleveland Guardians at PNC Park. Pittsburgh PNC Park Pennsylvania USA, EDITORIAL USE ONLY Copyright: xCharlesxLeClairex 20250419_nts_al8_0108
This year’s trade deadline felt like the same old story for the Pirates, more about shipping guys out than bringing any big names in. For instance, longtime faces like David Bednar and Ke’Bryan Hayes were dealt, along with lefty Caleb Ferguson. And in return? A batch of prospects, but no real headliners. Still, there was a bit of hope. Why? Because when the Pirates sent Hayes to the Reds, they also offloaded the $36 million left on his contract. And, Cherington mentioned that the money saved during these trades would be reallocated, but if Perrotto’s column is anything to go by, that’s not happening.
For context, the Pirates started the year at $85.5 million. And guess what? 2026 is shaping up to be more of the same. Don’t expect any big-name signings or a turnaround in the team’s approach, but a few chants of “sell the team” echo through the ballpark. And, amid all the chaos around the Pirates, one thing is common. Rumors of Paul Skenes getting extended by the team or if he is getting traded.
Paul Skenes remains the center of discussion for the Pirates
After yet another frustrating trade deadline, the only real hope left for Pirates fans is whether the team can lock up Skenes with a long-term deal. And to their credit, the Pirates have reportedly reached out to Skenes recently to explore that possibility. But let’s be real, it’s looking like a total long shot.
The odds were slim already. Because asking Skenes to delay his shot at free agency for a team that hasn’t shown any willingness to build a legit contender around him is a tough sell. And then the Red Sox went and signed Roman Anthony to an eight-year, $130 million extension. Yes, Anthony’s good, no doubt, but Skenes is better, more proven, and plays a premium position. So, if Anthony’s getting that kind of money, Skenes’ price tag likely starts north of $200 million.
Do you really believe the Pirates are going to spend that kind of cash? Notably, this is the same organization that hasn’t had a payroll over $100 million since 2017. So, unless something drastically changes, a massive extension for Skenes seems more like a pipe dream than a plan.
The post Pirates Payroll Plans Surface Amid Paul Skenes Extension Rumors and MLB’s Spending Scrutiny appeared first on EssentiallySports.