Python is relatively low on the kind of boilerplate Java has.

(Or if you want to go more extreme, Haskell can really give you some terse programs.)

I'm not the OP.

As someone who has worked with both in a professional setting, Python has a lot of similarities with COBOL, IMO.

As someone who has also done that, the most important thing in common is that they're programming languages. COBOL is a rigid and "square" language, I'm tempted to call its style "COBOLic".

Any language where the dots at the end of statements are crucial part of the logic flow can't be that similar to Python.

Can you explain how? As someone that has worked with both professionally, I can't see many similarities.