Correctly removing the default Python installation
What you're doing is destructive. Each apple update can and will either break or re-introduce parts or all of the python files to are about to delete.

Why don't you simply change your path so that the homebrew version of the tool is used?

The danger of hacking the core OS is that it's tightly bound into receipts and software update by Apple and you risk compromising the stability of the system when you're modifying it. Generally the skill level needed to augment the path is far, far less than that needed to continually manage and troubleshoot a custom OS where you've removed components from outside /Applications .



You can delete the pip files from /usr/local/bin since they are not Apple or system installed and you can re-download them or re-install them with brew once you pick your version of choice there.