I am at a loss, SSL: CERTIFICATE_VERIFY_FAILED

Server
2

Can you run:

curl -X GET -I https://pypi.python.org
openssl s_client -connect pypi.python.org:443 -showcerts 2>/dev/null | openssl x509 -noout -subject -issuer -modulus
ls -lah /etc/ssl/certs/ca-bundle.crt