Python 2.7 not working anymore: cannot import name md5
I had the same problem on macOS.
brew reinstall python@2
solved this problem.
Maybe you could try to reinstall python.
In this post might be a solution:
The python2.7 package is dependent to the libssl1_0_0 package (openssl_1.0 runtime librairies).
So you need to install it, and add the /usr/local/ssl/lib directory in $LD_LIBRARY_PATH environnent variable.
I too came across the same issue in macOS which I could not solve using the brew reinstall python@2
command.
So then I used the following command which worked for me.
brew reinstall https://raw.githubusercontent.com/Homebrew/homebrew-core/94d572a132a63651739fef1931f540404b7eaa31/Formula/python%402.rb