Apparently this error log has been reported multiple times in different case scenarios with also different solutions. I will leave these so you can check them. Some use different technologies but you can verify the solutions related to gcloud.
https://stackoverflow.com/questions/46832451/transporterror-httpsconnectionpool
https://stackoverflow.com/questions/62692704/python-google-oauth2-cannot-connect-to-proxy
https://stackoverflow.com/questions/69046003/error-while-trying-to-connect-to-google-cloud-storage
This is the more similar to your case: https://stackoverflow.com/questions/68982548/gcloud-init-error-gcloud-crashed-connectionerror
Also recommend you to try to get more information about the error so we can get a more specific solution here and could you run the following commands as seen here:
gcloud info
To check network connectivity and hidden properties, run:
gcloud info --run-diagnostics
To print the contents of the most recent log file, run:
gcloud info --show-log