Rubys biggest downfall was the stupid "fancy" syntax stuff in the language, like not requiring parenthesis or return statements, insert operators, BEGIN/END blocks, e.t.c. All of those make the code base harder to read.

Also I remember the dependency management system was a pain in the ass to deal with, especially with modules with native libraries.

Python had some issues with 2, but when 3 came around and fixed all that, it became the language of choice specifically because of its consistency.