TS might transpile to JS and can always be split into a js and type annotation file but is it's own language developed in tandem with the type check based on a holistisch approach to find how to type check then and then put it into the syntax and type checker.
Thats not true for python at all.
Python types where added as annotations to the language many years ago, but not in a holistic approach but in simplistic approach only adding some fundamental support and then extended bit by bit over the years (and not always consistently).
Furthermore this annotations are not limited to type checking which can confuse a type checker (through Annotated helps a lot, but is also verbose, wonder how long until there is a "Annotated" short syntax e.g. by impl @ on type or similar).
Basically what the type annotation feature was initially intended to be and what it is now differ quite a bit (dump example `list` vs. `List`, `Annotated` etc.).
This is made worse that a bunch of "magic" is deeply rooted in python, e.g. sub-classing `Enum`. Sure you have that in JS too, and it also doesn't work that well in TS (if you don't add annotation on the dynamically produced type).
Lastly TS is structurally typed, which allows handling a bunch of dynamic typing edge cases, while Python is, well, in-between. Duck-typing is (simplified) structural typing but `isinstance` is a common thing in Python and is nominal typing...
So yeah it's a mess in python and to make it worse there bunch of annoyances related to ambiguity or to many ways how to do a thing (e.g. re-exports+private modules, you can do that common coding pattern, but it sucks badly).
