Python 2 removed from homebrew.
Python 2.7 is not getting any security/crypto updates backported. Eventually PyPI's SSL configuration will change to a point where Python 2.7 won't handle it and then that's it. Game over, no more pip for you, even if you froze on < 21.0.
There are Linux distros out there in LTS until late into this decade that shipped with Python 2.7. Ubuntu 18 comes to mind, which EOLs in 2028. They've got a real hard problem to solve.