> back when Python (or Ruby) didn't even have type hints (not type checkers, type hints!), it would easily outperform pretty much every heavily typed language?

No it didn't. It outperformed Java 1.2, and people thought that Java 1.2 was what a typed language looked like. Python always sucked compared to OCaml (yet alone OCaml with a decent IDE), but OCaml had a weird syntax and the documentation was in French, so no-one cared. Now that we finally have a copy of OCaml with curly braces and a critical mass of obnoxious fanboy hype, more people have noticed.