Python's type annotations are in fact very similar to Flow and Hack in the sense that they provide gradual typing. The specification (see: PEP 484) describes that only annotated functions are type checked. Calls to non-annotated code are treated as accepting any type in arguments and returning the Any type (a special type which effectively silences the type checker).
This generates a chicken and egg problem: if you don't have enough functions annotated, the type checker won't be able to provide meaningful output to you. So convincing people to annotate their code is harder: they don't see the benefit right away. Worse yet, you already have tens of thousands of functions in your code that you know work in production but were written before type annotations were introduced. It's not really feasible to come back and fill this information manually.
MonkeyType is a tool that gathers types at runtime and enables putting them back in your code as annotations. The goal is for mypy to have more information to work with, making it way more useful.