Pirates Front Office Under Pressure in 2026

PITTSBURGH — The Pittsburgh Pirates look like they'll finally break through this season, make the playoffs and get back to winning ways, but that's no guarantee with how topsy-turvy things can occur.

The Pirates front office, led by general manager Ben Cherington and team president Travis Williams, both head into their seventh season in charge and yet to see serious success.

It's likely why the Pirates ended up one of the teams/front offices/managers in the "Feeling the Heat" category in the spring preview survey from The Athletic, with Jayson Stark talking with 36 executives, former executives, managers, coaches and scouts about who's under the most pressure.

The Pirates have made the moves that signal they want to compete, but if they fail, it's likely there could be some serious personnel changes.

Why the Pirates Front Office Is Under Pressure

The Pirates haven't had success under Cherington, with a 365-505 record, a .420 winning percentage. Only the Washington Nationals, 354-416 (.407) and the Colorado Rockies, 331-538 (.381) have had worse records than them during the past six seasons.

This includes the worst record in baseball in 2020 at 19-41 overall, a shortened season due to the COVID-19 pandemic, back-to-back 100-loss seasons in 2021 and 2022, collapses after a great start in 2023 and being in National League Wild Card contention after the trade deadline in 2024, where they went 8-19 in August.

Pittsburgh also finished 71-91 in 2025, last in the NL Central Division and the fifth worst record in baseball.

The Pirates also started the season 12-26 and Cherington fired manager Derek Shelton, who he hired as manager after taking over late in 2019.

Pirates fans voiced their displeasure throughout 2025 towards ownership, the front office and management.

Williams himself came under fire for the team's handling of the Bucco Bricks, the commemorative pavers outside PNC Park, which ended up in a recycling plant without prior knowledge to the owners.