If the 2026 Pirates had actually reached October, would you trust them? Paul Skenes and Jared Jones give Pittsburgh a dangerous one-two punch, while Mason Montgomery and an improved bullpen could shorten games. But the lineup’s struggles against lefties and a shaky defense become much bigger problems when every mistake matters. The NS9 crew builds its hypothetical playoff plan before looking ahead to Konnor Griffin, Oneil Cruz and what could finally push Pittsburgh into October in 2027.