Donald Stufft added the comment:

I think 1.0.2 is the only version of OpenSSL that has the ability to short 
circuit the chain validation which is something that makes it easier for 
libraries like requests to remove the weak 1024 bit roots from their SSL 
certificate store.

It's also needed for ALPN support which libraries like hyper will need in order 
to support HTTP/2.

I'm pretty massively +1 in Python shipping 1.0.2 (or really, whatever the 
latest OpenSSL is) wherever it can, including the OSX installers even on 
systems where Apple ships it's ancient OpenSSL.

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<http://bugs.python.org/issue23686>
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