Just an update that having a version of Ansible that was installed with Homebrew, as opposed to pip can also cause this error. As of today looks like ansible 2.4.2 is the version we want. At least version 2.4.
I think it’s basically brew uninstall ansible and pip install ansible==2.4.2.
which ansible
which python (needs to be 2 and not 3 until later this year, I read)
which openssl
Might also be insightful. For me I’m using versions located in /usr/local/bin, which is in my $PATH before local/bin so that those commands will find binaries to use there before getting to system versions which are probably located in /usr/bin.
I’m not quite clear on how or why exactly the brewed Python pip installs one version of openssl, while the brew-installed openssl is different.