I\'ve been trying to install pip on macOS sierra via brew, but every time it completes without installing the binaries in /usr/local/Cellar/python/2.7.13/bin.
OK gang, lots of these answers where helpful but none of them got me to the finish line. I am running High Sierra 10.13.4. The problem as documented above is that Brew installs pip in the /usr/local/bin directory but Python is in /usr/bin (although as Carl said, Python3 correctly goes to /usr/local/bin).
My immediate use case is related to getting the Postgres BigSQL package to install.
The steps I took are as follows:
$ rm -rf ~/Library/Caches/Homebrew$ sudo rm -rf /usr/local/lib/python2.7/site-packages$ brew reinstall python This pulls down python-3.5.6.high_sierra and put it in /usr/local/bin/python3which python still shows /usr/bin/pythonbrew install python@2 which pulls down python@2-2.7.14_3.high_sierrawhich python shows the correct path /usr/local/bin/python which is also where all your pip stuff is installed, so now pip will work.sudo pip install --upgrade pip