The Pittsburgh Pirates finished the 2025 season with a 71-91 record, which is technically worse than their 2024 campaign, which ended at 76-86. The Pirates are headed in the wrong direction, but there were a few bright spots this year. Namely, Paul Skenes is expected to win the NL Cy Young award. The Pirates also found a long-term manager, one they hope will finally lead them back to the postseason, in Don Kelly.
Surprisingly enough, the Pirates decided to keep Ben Cherington in charge of baseball operations. Cherington has been with the Pirates since 2019, when he took over for then-POBO Neil Huntington. Since the season ended just a week ago, we don't have many early reviews of the Pittsburgh offseason. What has come out of that locker room was not kind to the team's direction or owner Bob Nutting? We know this thanks to the reporter I interviewed for this story, Noah Hiles of the Pittsburgh Post-Gazette.
“People think we’re underachieving,” one player told Hiles and the Post-Gazette in early May. “Look around here. We’re playing to our potential. This is what $90 million gets you."
“Some of the teams we play aren’t even trying to win. They’re rebuilding but still have a higher payroll than us,” the same player noted later on. “What do you think that tells us?”
The Pirates' end-of-season payroll was a shade over $84 million. That ranks 23rd in the majors. While player spending isn't the only determining factor in whether a team can contend any given season, the Pirates have proven time and time again that the number does matter. Even when Pittsburgh was competitive from 2013-15, they were often missing a key piece, whether it be a big bat or another arm, to put them over the top.
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Pirates Q&A with the Pittsburgh Post-Gazette's Noah Hiles
Following this Pirates season, Noah Hiles will transition to a sports enterprise role with the Post-Gazette. However, before he leaves the Pirates beat (officially!) he spoke to FanSided about the season he just covered, and what's to come in what should be a tumultuous offseason. Hiles reported in his end-of-season column that Pittsburgh wasn't expected to dramatically increase payroll in 2026. So, how do Cherington and Nutting expect to improve the team?
MP: How should the Pirates build around Paul Skenes, and do you believe Ben Cherington can meet those expectations given the resources available to him?
NH: It’s pretty simple. The Pirates need to add bats. They’re in desperate need of a better slugging percentage. No one on their team can hit for power, so finding established middle of the lineup hitters is an absolute must. I’m not sure it will happen — in fact, I’m quite skeptical it will.
MP: What is the reaction around Pittsburgh regarding Don Kelly's contract and the return of Ben Cherington? Is Cherington's return a surprise to those in the know?
NH: No one seems to be upset over Kelly’s extension. Everyone seems to be upset over Cherington being retained. Most fans have a hard time understanding how a GM that’s had six-straight losing seasons remains employed with this team. But those following along, who cover the team, weren’t that shocked by either move.
MP: What does Andrew McCutchen's future hold?
NH: I’m not sure what the future looks like for Cutch. He wants to be here, but he also wants to win. I don’t think he has much faith in this current regime. I’m also not sure if he’s the best fit here, moving forward. He’s coming off the worst season of his career. I’m not sure who else would sign him to be an everyday player, and he doesn’t play enough in the field to be a platoon option. It feels like it’s Pittsburgh or bust for him at this point, and the Pittsburgh future is in serious question.
MP: Is there any expectation Bob Nutting will increase payroll this winter, or is it too soon to tell? If not, where should the Pirates invest their limited payroll?
NH: I don’t expect payroll to be much higher, if at all. I wouldn’t even be shocked if it was lower on opening day. Revenue wasn’t what they thought it would be in 2025, and this owner isn’t spending more to fix it. Whatever money they do have to work with must go toward the outfield and third base. Bats. Slugging. Those two things are the focus.
MP: This season was a bit of a PR nightmare for the Pirates. What steps can they (or have/will they take) to rebuild some trust with the fan base?
NH: Overall, the only thing that fixes this is winning. This year was a disaster in all areas. The first day of the offseason was equally bad. Fans are more upset than ever, which is truly saying something. They want to see a winner, and don’t believe that can happen if the Pirates continue this same approach they’ve had for years, which looks to be their plan again in 2026.
Takeaways: The Pirates are pretenders until further notice
Based on Noah's answers, it's tough to consider the Pirates anything close to contenders. Yes, they finished in the top-10 in most major pitching categories. That is a nice step, but the team is also reportedly considering a Mitch Keller trade this winter, and parted ways with pitching coach Oscar Marin. And, as Hiles suggested, they don't plan on adding payroll this winter. Where will the improvement come?
The Pirates have Andrew McCutchen and Tommy Pham coming off the books. If they let both of those players walk – which I wouldn't recommend, given Cutch is a franchise icon and Pham did show flashes at times in the second half – they will gain $9 million in payroll. Perhaps there is room to trade lucrative contracts elsewhere. That would probably come in the form of Keller, which would make the pitching staff actively worse.
Pittsburgh has real building blocks in Paul Skenes, Bubba Chandler, Oneil Cruz, Bryan Reynolds and (possibly) No. 1 overall prospect Konnor Griffin. If Cherington squanders another year of that core, he should be shown the door.