Ben Cherington’s biggest Pirates roster failures are hiding in plain sight on playoff benches

Writer Emma Lingan argues that general manager Ben Cherington's roster construction failures are evident as former Pittsburgh Pirates regulars appear on MLB playoff rosters as bench depth. Rowdy Tellez, Tommy Pham, Bryan De La Cruz, and Isiah Kiner-Falefa all secured postseason roster spots with other clubs after being heavily relied upon as starting fixtures in Pittsburgh.

Lingan contends that playoff teams correctly view these players as complementary pieces, whereas Pittsburgh treated them as foundational offensive starters. Despite finishing 82-80 in 2026 to snap a streak of losing seasons, the Pirates missed the postseason again, which Lingan attributes to repeatedly substituting depth players for legitimate everyday talent.