Pirates lockout fears may hand Ben Cherington lifeline fans will hate

If Pittsburgh Pirates fans were hoping the 2026 season would finally force the organization to make a definitive decision on Ben Cherington, they might not like where this is headed.

FanSided MLB insider Robert Murray said this week he is leaning toward Cherington remaining in Pittsburgh beyond this season, pointing to two factors: the general manager is already under contract through 2027, and uncertainty surrounding a potential MLB lockout could make the Pirates reluctant to overhaul their baseball operations department.

That would be quite the lifeline for Cherington. He has been running the Pirates' baseball operations department since November 2019 without a single winning season to show for it, and his deal runs through the 2027 season. But allowing the final guaranteed year of a contract to dictate a baseball decision would be especially difficult to defend after seven seasons.

The Pirates entered 2026 openly expecting to contend. They finally spent more aggressively, extended Konnor Griffin and approached the trade deadline as buyers rather than commencing another selloff. Cherington himself said around the deadline that Pittsburgh believed in its roster and wanted to give the group every opportunity to reach the postseason.

Yet another late-season fade has left the organization facing many of the same uncomfortable questions about roster construction, player development and whether Cherington should remain the person making the biggest decisions.

MLB's looming labor battle may buy Pirates GM Ben Cherington another year of job security

Baseball's looming labor situation could complicate everything. MLB's current collective bargaining agreement expires Dec. 1, and negotiations have already centered on potentially transformative issues such as a salary cap and floor. MLB has also proposed significant changes to the offseason transaction calendar, including potential quiet and frozen periods.

Changing general managers immediately before that uncertainty would undoubtedly create logistical challenges. A new baseball operations leader could inherit a roster, payroll structure and offseason unlike anything executives have dealt with under the current system.

But that can't become an excuse for avoiding accountability. Organizations replace executives under imperfect circumstances all the time. Pittsburgh's decision should ultimately come down to whether ownership believes Cherington is the right person to maximize a window built around Griffin, Paul Skenes, Oneil Cruz, Bubba Chandler and the rest of its young core.

If the answer is yes, the Pirates should say so and own it. If the answer is no, the possibility of a lockout shouldn't buy Cherington another year.

Pirates fans have already spent most of this decade being asked to wait for Cherington's plan to produce sustained winning. Asking them to accept labor uncertainty as another reason to wait until 2027 would understandably feel like moving the finish line one more time.

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