I don't have any data to back this up, but I suspect solid Windows support was a big driver of that. I used to do a fair bit of Python before Ruby and there was a nice MSI installer for the runtime and plenty of libraries had precompiled Windows installers available. This was important because we were working with some software that necessitated running Windows.
I love Ruby, but when I started developing in it, I was surprised at how much the Windows experience lagged behind just about everything else I had tried up until that point (Java, Python, Perl, x86 Assembly, at least). Even today, it's not really easy to run for anything requiring native extensions. You have to set up a separate compiler* just to build those extensions because most gems don't push binaries out. That may be better for security, but I don't think that's the driving factor. You're better off just running JRuby, assuming WSL isn't an option.
* Granted, RubyInstaller makes this a lot easier nowadays.
I love Ruby, but when I started developing in it, I was surprised at how much the Windows experience lagged behind just about everything else I had tried up until that point (Java, Python, Perl, x86 Assembly, at least). Even today, it's not really easy to run for anything requiring native extensions. You have to set up a separate compiler* just to build those extensions because most gems don't push binaries out. That may be better for security, but I don't think that's the driving factor. You're better off just running JRuby, assuming WSL isn't an option.
* Granted, RubyInstaller makes this a lot easier nowadays.