In terms of statically compiling libssl, I believe that can not be legally done without re-licensing all of Sublime Text and Python as LGPL since openssl is licensed at LGPL. However, if you dynamically link LGPL code, the license does not require the calling code to be be licensed as LGPL.
I did the work of getting _ssl.so for linux working for the SFTP package. I have offered the _ssl.so modules and python to properly import them to other people writing open source software. See sublimetext.userecho.com/topic/5 … ent_165820 for some more details of where to find it.
I know one user added it to their project, but just because you have the _ssl module, does not mean httplib will automatically be able to request https URLs because the HTTPS functionality of httplib is enabled when httplib is first imported. I think they did some work trying to remove the httplib module and re-import it, but I don’t know if they ever got it working. I am only using it for ftplib, and I have a custom version of that anyway to fix lots of bugs, so I did not have to deal with removing and re-importing it.
Package Control gets around this by using curl or wget on linux. There is even a whole bunch of code to handle proxies properly and verify SSL certificates. However, it sounds like the library you are using is bound to using httplib.