The Pittsburgh Pirates’ 2025 season is up in the air because the organization’s leadership structure is unclear. After another disappointing season in which the team lost for the seventh straight year, the franchise’s top decision-maker is fighting to keep his job while chairman Bob Nutting thinks about making big changes to the organization.

The worries about performance come from a season that started with chairman Bob Nutting’s statement that the Pirates “need to win more,” only to see the team lose its seventh straight season and head toward 90 losses. Ben Cherington, the Pirates’ general manager, has overseen a roster that ranks dead last in Major League Baseball with just 548 runs scored—33 fewer than even the historically poor 42-win Colorado Rockies. The offensive futility extends across every major category, with the Pirates sitting at baseball’s bottom in home runs, RBIs, slugging percentage, and OPS.

Facing mounting pressure and questions about his future, Cherington delivered an impassioned defense of his tenure during a recent press conference at PNC Park. “I’m certainly doing the job that way,” Cherington stated when asked about his expectations for next season, with two years believed to remain on his contract. “I don’t do the job because of the job. I do the job because I want to be a part of making this thing work. Winning more games and being able to leave PNC Park at night feeling better, and everybody feeling better. That’s why I do it. I still want to do it. I badly want to do it.”

The situation has created ripple effects throughout the organization, particularly affecting interim manager Don Kelly, who replaced Derek Shelton after his May dismissal. Kelly has posted a 53-63 record since taking over, but the team lost 12 of 13 games entering the weekend. Cherington offered measured praise for Kelly’s tenure, stating, “He’s an excellent communicator. He’s dogged in his approach to the job. He has a high self-belief. He believes in people. I believe he cares about other people more than he cares about himself.” The general manager specifically highlighted Kelly’s courage under pressure: “I’ve been particularly impressed by his willingness to go after some really hard things, too. It’s not easy when you don’t have the full mandate of a permanent job to do that. He’s done it anyway.”

Chairman Bob Nutting is in a position where major changes to the organization seem more and more likely because of the pattern of lukewarm endorsements followed by dismissals. Nutting is under a lot of pressure to decide if the current leadership structure can create the winning culture he wanted at the start of the season. This is because there have been a lot of management changes that haven’t worked, and the team’s offense is at an all-time low.

While the front office makes these leadership decisions, the company has another important choice to make that could shape its future. These evaluations of employees are happening at the same time as talks about the franchise’s most valuable asset.

Pirates face Paul Skenes’ contract decision amid front office uncertainty

Cherington is fighting for his own job security, but things are getting even more complicated for the Pittsburgh Pirates’ offseason plans because of rookie sensation Paul Skenes. Jon Heyman, an insider for Major League Baseball, recently said that Pittsburgh is still “likely to extend” their ace, even though big teams like the New York Yankees were interested in Skenes and reportedly went after him with prospects Spencer Jones and George Lombard Jr. before the trade deadline.

The 22-year-old phenom has maintained his focus strictly on baseball during these crucial final weeks. “No. That’s not something I want to discuss during the season,” Skenes told reporters when questioned about potential contract negotiations before his final start. “They haven’t brought anything up to me out of respect for that, too. No discussions on that.” His disciplined approach mirrors the organization’s stated intention to handle extension talks after the season concludes.

Pittsburgh fans, on the other hand, have real worries about whether the team’s owners are serious about building around elite players. Since 2019, the franchise has not had a winning record, so 2025 will be its tenth straight season without playoff baseball. Bob Nutting has always been careful with his payroll, which makes people wonder if management will spend enough money on supporting players around their young core.

With Skenes anchoring a promising rotation that includes Jared Jones, Bubba Chandler, and Mitch Keller, the foundation looks strong. But talent alone can’t fix problems in an organization. If Cherington can negotiate Skenes’ extension and if ownership gives the team the tools it needs to compete, this young core could be a real source of hope for Pittsburgh or just another cycle of unfulfilled potential.