> Would a more rigorously-typed alternate-universe Python have been as successful?

Maybe at some point we'll get TypedPython (like we got TypeScript).

In my opinion that's the way language design should be done.

First discover what semantic people want to use to express themselves and if you got that right enough then try to describe that semantic with a type system as rich as you need to let people express themselves more precisely.

Starting with designing typesystem is too hard and leads to fiasco that kept Haskell in obscurity and spawned whole slew of dynamic languages.

Although maybe we got better at making flexible enough type systems... Rust seems to be doing a lot of stuff right.