The Pittsburgh Pirates have not appeared in a postseason game in a full decade. Their last October experience came to an abrupt end on a cool night at PNC Park against the Chicago Cubs when soon-to-be-named 2015 NL Cy Young Award winner Jake Arrieta walked the walk, tossing a complete game shutout in a 1-0 Cubs victory.
Coming off a 71-91 record in 2025, Pittsburgh has its work cut out for it if it wants to snap that streak next season. Despite having Paul Skenes atop the rotation, the Pirates have finished in last place in the division in each of the last two years - but they're hoping to start trending in the right direction sooner rather than later.