If you think about it from the perspective of people learning programming, python is dead dead simple. In Unix like systems it comes preinstalled most of the time. For so many students in many parts of the world who use an HP/Lenovo laptop for university work the OS is windows and python installation is again, dead dead simple.

Ruby starts off by saying you should have a version manager. And windows installation is not straightforward (from a student perspective it’s important to note that something that looks like it isn’t officially supported makes it feels like the entire language is going to be a compatibility slog). This is not dead dead simple. It’s not hard. But it requires more than one concept to be learned to start.

Then the docs. Ruby has so many ways of getting started. Python puts up one main way. Same for the api reference. Python has a single link and they even say “keep this under your pillow”. As a beginner I know what I should do. Ruby? Many links that say arcane stuff (beginner perspective) like rdoc and what not. Python is super clear in their breakdown of reference too. I cannot stress enough how simple this page (https://docs.python.org/3/library/index.html) makes it to find what you want.

Overall Ruby and it’s documentation feels like it’s made for people who know Ruby or something more than the bare minimum. Python is made for people who’ll be trying out programming itself for the first time.

To me, that’s what made Python win. They just seemed like they thought more about folks starting out for the first time.