Ned Deily added the comment:

Yep, 0.9.8 is the newest and presumably last major of version of OpenSSL in OS 
X. OpenSSL has been officially deprecated by Apple in OS X since OS X 10.7; 
it's only there for third-party products shipped by Apple in OS X, like Python. 
 Their own apps use Apple's own frameworks like SecTransform and CommonCrypto.  
(See, for example, 
http://rentzsch.tumblr.com/post/33696323211/wherein-i-write-apples-technote-about-openssl-on)
 Apple also ships 0.9.7 shared libs in 10.10 for really old applications.

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<http://bugs.python.org/issue23345>
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