Pirates fans' numbness can't make them lose sight of Ben Cherington's empty promises

The Pittsburgh Pirates hired Ben Cherington as general manager in 2019 to oversee a long-term rebuild. By 2025, that’s six full seasons, and the Pirates are still nowhere closer to contention. In fact, they're farther away.

The Pirates have seven games left in the 2025 season. Even if they win all seven of those games, they will still finish with a worse record than each of the last two seasons. It's inexcusable, especially after Cherington promised progress following the team's back-to-back 76-win campaigns in 2023 and 2024.

Unlike some other small-market clubs – the Baltimore Orioles, Kansas City Royals and Cleveland Guardians, just to name a few – the Pirates haven’t turned their prospect depth into consistent Major League success under Cherington. There's no reason to believe that will change in year seven.

Top picks like Paul Skenes and Konnor Griffin remain the face of the future in Pittsburgh. But outside of a few blue-chip names, the pipeline has underwhelmed at the MLB level. Too many first-rounders and high-profile prospects like Quinn Priester and Henry Davis have struggled or plateaued in Pittsburgh, raising serious questions about scouting and development under Cherington.

Even with some homegrown talent, the Pirates are still short on impact bats and reliable depth. Failure to surround young talent with adequate veterans has led to repeated collapses, and there has been zero sense of urgency from the front office to turn things around.

Pirates finishing 2025 with worse record than last two seasons shows why it's time to show Ben Cherington the door

The Pirates remain one of MLB’s least active teams in trades and free agency. When they do spend, it’s on short-term stopgaps like Aroldis Chapman and Tommy Pham. There hasn’t been a bold move to accelerate the rebuild, leaving fans frustrated that the team is perpetually waiting for “next year.”

The fanbase has become increasingly skeptical that Cherington’s “patient” approach will ever lead to a winning product. That skepticism is reaching a boiling point, especially given that the National League Central is there for the taking.

Since Cherington took over in Pittsburgh, the Milwaukee Brewers have begun a reset; the Chicago Cubs have been inconsistent; the St. Louis Cardinals have been retooling; and the Reds have been young but uneven. The Pirates should have been in the mix by now, and Cherington failing to capitalize on this window should be seen as a massive missed opportunity.

After six seasons, the Pirates still lack a clear identity beyond “waiting for prospects.” As they wrap up yet another season in the basement of the NL Central, it's clear that Cherington’s cautious, development-first strategy isn’t enough — and a new GM with a more aggressive plan is needed.