Pirates might be nearing a Ben Cherington decision fans never saw coming

For most of Ben Cherington’s tenure, the idea of the Pittsburgh Pirates extending him would have sounded like a punchline to frustrated fans.

The rebuild dragged. The payroll complaints piled up. The big-league roster too often felt incomplete, even as the farm system slowly started to produce the kind of talent that was supposed to change everything. Pirates fans have had every reason to demand urgency, accountability and, finally, a team that looks like it is trying to win.

But now, uncomfortable as it may be for some fans to admit, the Pirates might be inching toward a Cherington decision few saw coming.

According to Ken Rosenthal, Cherington is under contract through 2027, and the Pirates’ current trajectory may make an extension a realistic conversation. That's not because Pittsburgh has suddenly become a finished product, or because the front office should be free from criticism. It's because the Pirates’ improvement has become much harder to ignore.

Pirates fans may have to brace for possible Ben Cherington extension in 2027

Rosenthal noted that despite an 8-12 start to June after a strong May, the Pirates entered Wednesday with the fifth-best runs-per-game mark in MLB, the ninth-best rotation ERA and a plus-23 run differential. Those are the numbers of a team that, even while dealing with injuries to key pieces like Konnor Griffin and Oneil Cruz, has shown signs that the plan may finally be translating.

In other words, Cherington’s active offseason is being validated in real time. The additions of Ryan O’Hearn and Brandon Lowe have helped give the Pirates’ lineup more credibility. Rosenthal also reported that Cherington is still trying to upgrade the roster, particularly the bullpen, while showing a willingness to discuss prospects and/or the No. 34 pick in this year's draft. That is the kind of aggression fans have begged to see from this front office for years.

None of this erases the skepticism. The Pirates still have to finish the job. Staying competitive is not the same as making the playoffs, and fans are tired of moral victories being sold as progress.

But this is where the timing gets complicated. With a lockout looming after 2027 and a possible salary floor that could dramatically alter how low-revenue teams operate, stability may matter more than ever. If the Pirates truly believe Cherington has positioned them for sustainable contention, they may not want to change leadership right before the sport’s economic landscape shifts.

Fans may not love it. But an extension is suddenly not unthinkable.

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