Upon reinstalling openssl with homebrew, I get the following info:

--------------
openssl is keg-only, which means it was not symlinked into /usr/local,
because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries.

If you need to have openssl first in your PATH run:
  echo 'set -g fish_user_paths "/usr/local/opt/openssl/bin" $fish_user_paths' >> ~/.config/fish/config.fish

For compilers to find openssl you may need to set:
  set -gx LDFLAGS "-L/usr/local/opt/openssl/lib"
  set -gx CPPFLAGS "-I/usr/local/opt/openssl/include"

For pkg-config to find openssl you may need to set:
  set -gx PKG_CONFIG_PATH "/usr/local/opt/openssl/lib/pkgconfig"
----------------

So assumingly the system-wide library should be preferred, may it be whatever one.

`/usr/bin/openssl version` says LibreSSL 2.8.3.

Probably I could still link to the homebrew installed SSL using the provided flags, but I'm quite sure this same problem will pop up at a lot of other Catalina users.