Sometimes in baseball, we look back and see a big mistake. For the Pittsburgh Pirates, a key decision from November 2019 is now getting a lot of heat. People are really questioning the hiring of their general manager. An MLB expert recently spoke out, not just blaming the GM, but also pointing a finger directly at owner Bob Nutting. This expert thinks Nutting made a really bad call, and it’s hurt the team for years.

The 2025 season has been another bitter one for Pirates fans to swallow. The team stumbled to a 12-26 record by May 8, a performance so bad that it got manager Derek Shelton fired. Don Kelly was named interim coach. By May 22nd, their record sat at a discouraging 17-33, a whopping 13 games behind the division-leading Cubs. The offense, in particular, has been dreadful. They are last in MLB with only 157 runs scored, and are also last in slugging percentage and OPS. They even matched a major league record with 26 straight games of scoring four runs or fewer.

This bleak backdrop prompted Jason Mackey of the Pittsburgh Post-Gazette to deliver a bold take. He argued that General Manager Ben Cherington “turned out to be the wrong choice — and I really hope Pirates owner Bob Nutting can see that.”

Mackey elaborated, “It should serve as a lesson in several ways, first and foremost to hire someone who’s worked in a similar market as opposed to a candidate who spent the majority of his career in Boston, a place that might as well as be the moon when compared to Pittsburgh on a baseball scale.” This critique directly questions Nutting’s hiring rationale.

Under Cherington — who has been on board since late 2019 — the Pirates have been consistently bad. The team went 294-414 in his first five seasons (2020-2024). That’s a 95-loss pace over a typical 162-game season. That puts Cherington among one of the worst GMs ever in MLB, given a six-season tenure. The club won 76 games in both 2023 and 2024 with little real progress despite some individual bright spots like pitcher Paul Skenes. The non-stop losing has, understandably, worn thin.

The unfruitful reign of Ben Cherington

Roster construction and player development under Cherington have also been fiercely criticized. The big-name trades or draft acquisitions, such as Endy Rodriguez, Liover Peguero, Jack Suwinski, Henry Davis, and Nick Gonzales, have mostly not come to make a significant impact at the MLB level. Davis, a former first overall pick, for example, was batting .191 in the first 99 games. The 2024-2025 offseason saw Cherington opt for low-cost veterans like Tommy Pham and Adam Frazier, which was criticized as not doing enough to address obvious team needs.

Cherington’s trades and free agent moves have been mostly conservative and haven’t paid off. He has not signed a single free agent to a guaranteed multi-year contract. Critics point to major trades involving stars like Starling Marte, Josh Bell, and Jameson Taillon as yielding “0 to show for it” in return. Many veteran hitters brought in, with few exceptions, have seen their performance “immediately gotten substantially worse” upon joining the Pirates. This trend raises serious questions about player evaluation and integration.

Adding another layer to the frustration, owner Bob Nutting reportedly meddled in baseball operations. Sources said that Nutting “stepped in to block at least one trade” involving closer David Bednar. This happened even as Bednar’s trade value was declining, with his ERA over 5.00 in both 2024 and 2025. Interfering like that negates the role of a GM in the first place, and it hampers the team’s chances of maximizing asset value.

Compare this to the Milwaukee Brewers, a team, roughly the same time the Pirates hired Cherington, was promoting Matt Arnold. Arnold, now their top baseball operations executive, was named Executive of the Year by three publications in December. Brewers owner Mark Attanasio called him “the glue in our baseball operations group.” Despite a $36 million payroll drop, the Brewers won more games last year than all but three MLB teams (Dodgers, Phillies, and Yankees). Arnold made savvy trades — acquiring William Contreras, and successful signings, such as Rhys Hoskins, and extending young star Jackson Chourio.

Many insiders and fans believe Nutting’s “profit-first” approach is the core issue. For the Pirates to truly turn a corner, a fundamental shift in ownership philosophy, empowering baseball operations with resources and autonomy, seems essential. Otherwise, the cycle of frustration in Pittsburgh is likely to continue.