Do which -a ansible: are you using the Ansible you installed (probably to ~/.local.bin) or the system Ansible, installed through your package manager (probably in /usr/bin)? If the latter, you need to add Pip’s user-bin to your PATH.
But if I don’t, it tries to uninstall ansible 1.9.4:
$ sudo pip uninstall ansible The directory '/Users/myuser/Library/Caches/pip/http' or its parent directory is not owned by the current user and the cache has been disabled. Please check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag. Uninstalling ansible-1.9.4: /Library/Python/2.7/site-packages/ansible-1.9.4-py2.7.egg-info /Library/Python/2.7/site-packages/ansible/__init__.py .... .....
if you are on OS X there is an issue with the 'protected filesystem'
which does not allow sudo + pip --upgrade to work. you need to
uninstall and reinstall Ansible.