I have experienced the same pain as the author many times, and, though I mostly work with Java by day these days, when possible I would much more happily reach for Python when I'm needing to hack on a REST API.

But I don't think this particular issue has much, if anything, to do with dynamic vs. static typing. It's mostly about how clean and elegant Python's way of handling JSON is compared to the black hole of viral enterprise-y overdesign that is Jackson, Java's de facto standard library for dealing with JSON.

With Python, JSON is deserialized to, in essence, a dictionary that maps keys to values, where the values are either strings, arrays of values, or dictionaries.

With Jackson, it's exactly as awful as TFA describes.

But I can easily imagine a Java library where JSON deserializes to some "JSONEntity" type that can act as either a string, a list of entities, or a string->entity map. And then I could interact with that in the same loose, don't-force-me-to-worry-about-details-I-don't-currently-care-about way that I do in Python. Perhaps one even already exists. It doesn't seem a far-fetched dream - I've used similar libraries for other static languages.

TBH, I haven't looked, because, even if I found one, I'd still be compelled to use Jackson, anyway. Because Jackson has been around forever, and Jackson is now so deeply entrenched that nobody working in the Javaverse can even fathom life without it. Suggesting such a thing would be heretical.