In the discussion of static vs dynamic typing solutions like typescript or annotated python were not really considered.

IMHO the idea of a complex and inference heavy type system that is mostly useless at runtime and compilation but focused on essentially interactive linting is relatively recent and its popularity is due to typescript success

I think that static typing proponents were thinking of something more along the lines of Haskell/OCaml/Java rather than a type-erased system a language where [1,2] > 0 is true because it is converted to "NaN" > "0"