As an outsider who only uses Python when I need a specific tool that's only available through pip: it's still one of my biggest nightmares. Every single time I need to install something with pip on MacOS there is this hour-long struggle with figuring out how to get the correct version of Python (2.7 vs 3) working with the correct version of pip working with the correct version of the library itself. I don't know, I g…
I don't have a Mac and maybe you've already tried this, but just in case, you can always do python2 -m pip install ... or python3 -m pip install ... to make sure it's running within that particular Python installation. You can use the --user flag to install to your user directory as well, if the system level is annoying.
Hell, it even breaks itself:
pip install --upgrade pip # => pip unusable
https://github.com/pypa/pip/issues/5447
https://github.com/pypa/pip/issues/5221
etc