Relevant page:

    https://docs.python.org/2/library/ensurepip.html

One may read:

    In most cases, end users of Python shouldn’t need to invoke
    this module directly (as pip should be bootstrapped by default),
    but it may be needed if installing pip was skipped when
    installing Python (or when creating a virtual environment) or
    after explicitly uninstalling pip.

As far as I correctly read the configure file that comes with the 2.7.11 tarball, the default is to behave as if --with-ensurepip=no had been passed.

As a result, that sentence fragment:

    (as pip should be bootstrapped by default)

may appear somewhat ambiguous for those compiling Python themselves.

Perhaps could this one avoid some head scratching:

    (as packagers are expected to have bootstrapped pip)

HTH,
Axel

Revision 4fc0154ec84a links here, but actually seems to be discussed in Issue 26348 and Issue 26664 instead.

As 2.7 is now EOL, I'm closing the issue.  Thanks for the report anyway, Axel!