[openssl-users] What does this error mean?

[Salz, Rich]

>    wget --no-check-certificate https://bootstrap.pypa.io/get-pip.py
  
When I try this:
	; ./apps/openssl s_client -connect bootstrap.pypa.io:443 -tls1_1
It fails.  When I leave off the last flag, it connects via TLS 1.2

So that website does not support anything older than TLS 1.2, apparently.  You'll have to build a modern OpenSSL, and then wget to use that version.  Good luck.