Solution for MacOS Catalina (10.15.2), python pip causes OpenSSL error in environment updated from old OS

TL;DR Make / Library / Developer / CommandLineTools something like CommandLineTools.bak mv and do xcode-select --install.

Why do so

It seems that the Command Line Tools that were included before upgrading to Catalina are mistakenly recognized as new even though they are old. So even if you do xcode-select --install, you will be told ʻalready installed`. To force it back in.

There are various correction methods written, but none of them was relevant

The following was irrelevant.

• Reinsert brew
• Reinsert OpenSSL with brew
• Insert MacOS10.14.pkg → I can't because there is no file in the first place.

Problem error string

$ pip install --upgrade pip
pip is configured with locations that require TLS/SSL, however the ssl module in Python is not available.
Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not avai
lable.")': /simple/pip/
Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not avai
lable.")': /simple/pip/
Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not avai
lable.")': /simple/pip/
Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not avai
lable.")': /simple/pip/
Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not avai
lable.")': /simple/pip/
Could not fetch URL https://pypi.org/simple/pip/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with ur
l: /simple/pip/ (Caused by SSLError("Can't connect to HTTPS URL because the SSL module is not available.")) - skipping
Requirement already up-to-date: pip in /usr/local/lib/python3.7/site-packages (18.1)
pip is configured with locations that require TLS/SSL, however the ssl module in Python is not available.
Could not fetch URL https://pypi.org/simple/pip/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with ur
l: /simple/pip/ (Caused by SSLError("Can't connect to HTTPS URL because the SSL module is not available.")) - skipping

Is brew bad or MacOS bad ...

It seems easier to do it on Cloud Shell (GCP). I can cry.