Installing pip on macOS Sierra

Question

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.

I've tried:

MacBook-Pro ➜ brew reinstall python

then:

MacBook-Pro ➜  ~ which pip
pip not found

I found the path to python, which is /usr/local/Cellar/python/2.7.13/bin but no binary for pip there.

I also tried the easy_install approach:

MacBook-Pro ➜ sudo easy_install pip
Traceback (most recent call last):
  File "/usr/bin/easy_install-2.7", line 11, in <module>
    load_entry_point('setuptools==18.5', 'console_scripts', 'easy_install')()
  File "/Library/Python/2.7/site-packages/pkg_resources.py", line 352, in load_entry_point
    return get_distribution(dist).load_entry_point(group, name)
  File "/Library/Python/2.7/site-packages/pkg_resources.py", line 2307, in load_entry_point
    return ep.load()
  File "/Library/Python/2.7/site-packages/pkg_resources.py", line 2021, in load
    entry = __import__(self.module_name, globals(),globals(), ['__name__'])
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/setuptools/__init__.py", line 12, in <module>
    from setuptools.extension import Extension
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/setuptools/extension.py", line 8, in <module>
    from .dist import _get_unpatched
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/setuptools/dist.py", line 21, in <module>
    packaging = pkg_resources.packaging
AttributeError: 'module' object has no attribute 'packaging'

UPDATE:

When I run brew postinstall python I am getting the following error:

MacBook-Pro ➜  ~ brew postinstall python
==> Using the sandbox
==> /usr/local/Cellar/python/2.7.13/bin/python -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --rec
==> /usr/local/Cellar/python/2.7.13/bin/python -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --rec
Last 15 lines from /Users/justin/Library/Logs/Homebrew/python/post_install.02.python:

Traceback (most recent call last):
  File "setup.py", line 92, in <module>
    cmdclass={'test': PyTest},
  File "/usr/local/Cellar/python/2.7.13/Frameworks/Python.framework/Versions/2.7/lib/python2.7/distutils/core.py", line 111, in setup
    _setup_distribution = dist = klass(attrs)
  File "/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/setuptools/dist.py", line 225, in __init__
    _Distribution.__init__(self,attrs)
  File "/usr/local/Cellar/python/2.7.13/Frameworks/Python.framework/Versions/2.7/lib/python2.7/distutils/dist.py", line 287, in __init__
    self.finalize_options()
  File "/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/setuptools/dist.py", line 258, in finalize_options
    ep.load()(self, ep.name, value)
  File "/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/pkg_resources.py", line 2020, in load
    raise ImportError("%r has no %r attribute" % (entry,attr))
ImportError: <module 'setuptools.dist' from '/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/setuptools/dist.pyc'> has no 'check_specifier' attribute

Answer 1

For what it's worth, after upgrading to high sierra I found my machine pretty much unusable for development, even crashing plenty of times.

Regarding python, i had a rights issue inside the site-packages folder, therefore the reinstall did not work out:

$ brew reinstall python

==> Reinstalling python
==> Downloading https://homebrew.bintray.com/bottles/python-2.7.14.high_sierra.bottle.tar.gz
Already downloaded: /Users/m/Library/Caches/Homebrew/python-2.7.14.high_sierra.bottle.tar.gz
==> Pouring python-2.7.14.high_sierra.bottle.tar.gz
==> /usr/local/Cellar/python/2.7.14/bin/python2 -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --record=installed.txt --install-scripts=/usr/local/Cellar/python/2.7.14/bin --install-
Last 15 lines from /Users/m/Library/Logs/Homebrew/python/post_install.01.python2:
.
.
.
copying build/lib/setuptools/script (dev).tmpl -> /usr/local/lib/python2.7/site-packages/setuptools
copying build/lib/pkg_resources/_vendor/packaging/version.py -> /usr/local/lib/python2.7/site-packages/pkg_resources/_vendor/packaging
error: could not delete '/usr/local/lib/python2.7/site-packages/pkg_resources/_vendor/packaging/version.py': Permission denied
Warning: The post-install step did not complete successfully
...

So to fix it, I completely removed the site-packages:

$ sudo rm -rf /usr/local/lib/python2.7/site-packages

With this, reinstalling python2, and having a working pip2 again, worked like a charm:

$ brew reinstall python

$ which pip2
/usr/local/bin/pip2
$ which python2
/usr/local/bin/python2

$ which pip
pip not found
$ which python
/usr/bin/python

Hope that helps.