Trying to use Python 2 under Trusty is hopeless, as pythonhosted.org has already started dropping support for non-SNI clients and will drop it completely soon, see https://status.python.org/incidents/hzmjhqsdjqgb and https://github.com/pypa/pypi-support/issues/978, and SNI is not available in the system Python 2 version (2.7.6, which is less than 2.7.9 in which it was added). Note that we still can't use Python 3 everywhere as long as we have macOS 11 builds as it's not available there.