Last time the Royals and Pirates both had winning seasons in the same year, was 1991. KC was just 82-80, while the Pittsburgh went 98-64 and pushed the NLCS to 7 games.
Last time the Indians and Pirates both had winning seasons in the same year, was 1979. Cleveland was lucky, being just 81-80, while the Pittsburgh won the World Series in 7 games over Baltimore. If you want to go back to the last time the Indians & Pirates both won 82+ games, then we’re talkin’ about 1965.
Ten of our current MLB teams didn’t even exist yet, including the Royals. Everyone born in that year, already had their major league career come and go.