C:\>py -3 -m ensurepip
Ignoring indexes: https://pypi.python.org/simple/
Downloading/unpacking setuptools
Downloading/unpacking pip
Installing collected packages: setuptools, pip
Cleaning up...
Exception:
Traceback (most recent call last):
  File "C:\Users\Red\AppData\Local\Temp\tmp8m44lvho\pip-1.5.6-py2.py3-none-any.w
hl\pip\basecommand.py", line 122, in main
    status = self.run(options, args)
  File "C:\Users\Red\AppData\Local\Temp\tmp8m44lvho\pip-1.5.6-py2.py3-none-any.w
hl\pip\commands\install.py", line 283, in run
    requirement_set.install(install_options, global_options, root=options.root_p
ath)
  File "C:\Users\Red\AppData\Local\Temp\tmp8m44lvho\pip-1.5.6-py2.py3-none-any.w
hl\pip\req.py", line 1435, in install
    requirement.install(install_options, global_options, *args, **kwargs)
  File "C:\Users\Red\AppData\Local\Temp\tmp8m44lvho\pip-1.5.6-py2.py3-none-any.w
hl\pip\req.py", line 671, in install
    self.move_wheel_files(self.source_dir, root=root)
  File "C:\Users\Red\AppData\Local\Temp\tmp8m44lvho\pip-1.5.6-py2.py3-none-any.w
hl\pip\req.py", line 901, in move_wheel_files
    pycompile=self.pycompile,
  File "C:\Users\Red\AppData\Local\Temp\tmp8m44lvho\pip-1.5.6-py2.py3-none-any.w
hl\pip\wheel.py", line 215, in move_wheel_files
    clobber(source, lib_dir, True)
  File "C:\Users\Red\AppData\Local\Temp\tmp8m44lvho\pip-1.5.6-py2.py3-none-any.w
hl\pip\wheel.py", line 193, in clobber
    assert not info_dir, 'Multiple .dist-info directories'
AssertionError: Multiple .dist-info directories

Storing debug log for failure in C:\Users\Red\pip\pip.log

C:\>py -m pip
C:\Python27\python.exe: No module named pip