Donald Stufft added the comment:

So here's a thought:

pip does have a CLI flag --force-reinstall which will uninstall and then 
reinstall whatever is being installed. If we modified things so that ensurepip 
supported this flag (or always used it with --upgrade) then it would fix this 
issue. The downside here is that only works with --upgrade.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue19693>
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