I think it's a toss up between Python and Ruby, but my bet is on Python.

Python is simple by design. It has optional typing (as of 3.6), beautiful async constructs (ala ES6), nice integration with C/assembly (in CPython), comprehensive open-source software ecosystem, and many strong alternative interpreters.

Ruby feels like it's playing catch-up in every area except metaprogramming... and, while I really enjoyed metaprogramming as an experienced engineer, I'm kinda glad Python lacks that complexity.