As Ronald is aware, there is also the issue that Apple has deprecated use of OpenSSL in OS X:

"Although OpenSSL is commonly used in the open source community, OpenSSL does not provide a stable API from version to version. For this reason, although OS X provides OpenSSL libraries, the OpenSSL libraries in OS X are deprecated, and OpenSSL has never been provided as part of iOS. Use of the OS X OpenSSL libraries by applications is strongly discouraged.

If your application depends on OpenSSL, you should compile OpenSSL yourself and statically link a known version of OpenSSL into your application."

In OS X 10.7, for instance, OpenSSL is at 0.9.8r. I think the same is true for 10.8. We should probably bite the bullet here and do as Apple urges, that is, supply our own libssl 1.0.x for the python.org OS X installer builds.

http://developer.apple.com/library/mac/#documentation/security/Conceptual/cryptoservices/GeneralPurposeCrypto/GeneralPurposeCrypto.html