While teams across the league, good or bad, are already reshaping their rosters for 2025, the Pirates’ front office is as quiet as ever. And honestly, nobody in Pittsburgh is shocked. Why? Because the Pirates’ owner Bob Nutting’s reluctance to invest in the team is practically tradition at this point. Instead, fans are growing frustrated watching a generational talent like Paul Skenes pitch without any real support.

Now, with reports surfacing that Skenes is open to being traded, it feels like the fans’ last bit of patience has finally snapped. The result? Saturday’s College GameDay in Pittsburgh showed a familiar sight from the fans. Recall what you have seen at every Pirates home game this year…

“Sell the team chants rained down from Pittsburgh fans after Pat McAfee mentioned that Paul Skenes won the Cy Young,” Jomboy Media reports.

Well, ‘Sell the team,’ chants are what you might be familiar with whenever you check out the stands at the PNC Park. And for the chants to come up and get heard, could not have a better time for the fans… It was just when McAfee announced that Skenes had just won the 2025 Cy Young award.

If you remember, Skenes addressed those chants back in April, saying the players needed to take responsibility for winning. Yet the Pirates still finished 71–91, marking their seventh straight losing season. Staying in the basement despite having an MLB-leading arm feels like a blatant injustice to Skenes, and fans haven’t been shy about saying it.

Paul Skenes’ rise only magnifies the frustration. He became one of the few pitchers in MLB history to win the Cy Young in his first full season, delivering strikeout numbers, velocity, and workload reminiscent of Dwight Gooden’s iconic rookie campaign. Talent like this is scarce, and contenders rarely waste a Cy Young arm’s early prime. That’s why the pressure on Pittsburgh’s front office has spiked — fans fear the organization is squandering a generational pitcher.

But the issue keeps circling back to the front office.

Nutting’s unwillingness to spend has long been one of the biggest frustrations in baseball. The Pirates entered 2025 with an $84 million payroll, ranking 27th in MLB, and Spotrac projects the 2026 payroll to drop even further.

That frustration is rooted in years of underinvestment. Pittsburgh has spent most of the Nutting era in the bottom five of MLB payroll, and from 2016 to 2024 they signed only one free agent to a deal worth more than $15 million.

Instead of building around their rising stars, they moved on from players like Gerrit Cole, Tyler Glasnow, Austin Meadows, and Joe Musgrove before they became expensive.

With a track record like that, fans can’t help but doubt whether real change is finally on the way.

But is there anyone listening?

Reportedly, back in April, veteran outfielder Andrew McCutchen didn’t shy away from the frustration boiling over in Pittsburgh. After “sell the team” chants rang out through a packed PNC Park, he admitted he understood exactly where fans were coming from. He even acknowledged how tough that kind of atmosphere can be on the players.

But what really pushes fans to go to such lengths is the complete lack of acknowledgement from the Pirates’ front office. Their silence is only making the fan base louder as they try to convey their message.

The Pirates might just be starting to hear the fans

It might sound uncommon to Pirates fans, but the team’s front office is finally set to work on what fans have been expecting. No, they are not selling the team, but it is rumored to be a spender this offseason!!!

According to MLB insider Mark Feinsand, Pirates GM Ben Cherington made it clear that he has zero intention of trading newly crowned NL Cy Young winner Paul Skenes. Now, that’s not a surprising thing to hear. What’s really surprising is that they’re finally ready to move in the opposite direction.

Well, the Pirates are planning to spend this offseason, a big change for a team that’s barely touched the free-agent market over the last decade. It’s still unclear how much they’re willing to shell out. But sources say they could add around $30–40 million to their 2026 payroll. And honestly, the timing couldn’t be better. Skenes just won the Cy Young, and Konnor Griffin has suddenly become one of baseball’s top young prospects.

But considering the Pirates haven’t signed a single multi-year free agent since Cherington took over in 2019, this all feels a little too good to be true. Still, better late than never.