Please refer to http://rkulla.blogspot.kr/2014/03/the-path-to-homebrew.html
After upgrading openssl to 1.0.1j by homebrew on MAC, but system python still referred to old version 0.9.8. It turned out the python referred to openssl. So I have installed new python with brewed openssl and finished this issue on Mac, not yet Ubuntu.
On Mac OS X version 10.10 and system python version 2.7.6, my procedure is as follows:
$ brew update
$ brew install openssl
Then you can see openssl version 1.0.1j.
$ brew link openssl --force
$ brew install python --with-brewed-openssl
You have to install new python with brewed openssl. Then, you can see /usr/local/Cellar/python/2.7.8_2/bin/python.
$ sudo ln -s /usr/local/Cellar/python/2.7.8_2/bin/python /usr/local/bin/python
Of course, /usr/local/* should be owned by $USER, not root, which is told by Ryan, but I used 'sudo'. And, before this instruction, I didn't have /usr/local/bin/python. After this instruction, you can use python version 2.7.8 not 2.7.6.
Finally, you can see as belows;
$ python --version
Python 2.7.8
$ python -c "import ssl; print ssl.OPENSSL_VERSION"
OpenSSL 1.0.1j 15 Oct 2014
Till now, I'm working on it on Ubuntu 12.04. If I have a solution for Ubuntu 12.04, then I will update my answer. I hope this procedure help you.
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