Tried multiple times with the last option ie -with-openss=/usr/local/ssl and did sudo make it still fails to make the ssl module and keeps complaining the same

Could not build the ssl module!

Python requires an OpenSSL 1.0.2 or 1.1 compatible libssl with X509_VERIFY_PARAM_set1_host().

LibreSSL 2.6.4 and earlier do not provide the necessary APIs, https://github.com/libressl-portable/portable/issues/381