Ned Deily added the comment:

This also affects the -m ensurepip installation of pip itself: the pip install 
fails trying to upgrade the Apple-supplied version of setuptools.  The behavior 
of adding the system Python's site-packages directory to the search path of all 
framework-build Pythons was deliberately added as a result of Issue4865.  I 
think experience has shown this was not a good idea because of the coupling it 
introduced between separate Python installations and some third-party 
distributors of Python on OS X already patch this code out.  It's currently 
only an issue for 2.7.x since Apple has not yet shipped versions of Python 3.x 
but the code should be removed there, too.

assignee:  -> ned.deily
nosy: +benjamin.peterson
priority: normal -> release blocker
stage:  -> patch review
title: pip failures on macOS Sierra -> ensurepip and pip install failures on 
macOS Sierra with non-system Python 2.7.x
type: compile error -> 
versions: +Python 2.7

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