Informações do ambiente:
$ which python
/usr/bin/python
$ python
Python 2.6.1 (r261:67515, Jul 7 2009, 23:51:51)
[GCC 4.2.1 (Apple Inc. build 5646)] on darwin
$ echo $PATH
/opt/local/bin:/opt/local/sbin:/sw/bin:/sw/sbin:/usr/bin:/bin:/usr/sbin:/sbin:/usr/local/bin:/usr/X11/bin:/usr/X11R6/bin:/opt/local/bin:/Developer/Platforms/iPhoneOS.platform/Developer/usr/bin:~/.utility_scripts
$ which easy_install
/usr/bin/easy_install
Especificamente, vamos tentar o módulo simplejson (eu sei que é a mesma coisa que importar json na 2.6, mas esse não é o ponto)
$ sudo easy_install simplejson
Searching for simplejson
Reading http://pypi.python.org/simple/simplejson/
Reading http://undefined.org/python/#simplejson
Best match: simplejson 2.1.0
Downloading http://pypi.python.org/packages/source/s/simplejson/simplejson-2.1.0.tar.gz#md5=3ea565fd1216462162c6929b264cf365
Processing simplejson-2.1.0.tar.gz
Running simplejson-2.1.0/setup.py -q bdist_egg --dist-dir /tmp/easy_install-Ojv_yS/simplejson-2.1.0/egg-dist-tmp-AypFWa
The required version of setuptools (>=0.6c11) is not available, and
can't be installed while this script is running. Please install
a more recent version first, using 'easy_install -U setuptools'.
(Currently using setuptools 0.6c9 (/System/Library/Frameworks/Python.framework/Versions/2.6/Extras/lib/python))
error: Setup script exited with 2
Ok, então eu vou atualizar as ferramentas de configuração ...
$ sudo easy_install -U setuptools
Searching for setuptools Reading
http://pypi.python.org/simple/setuptools/
Best match: setuptools 0.6c11
Processing setuptools-0.6c11-py2.6.egg
setuptools 0.6c11 is already the
active version in easy-install.pth
Installing easy_install script to
/usr/local/bin Installing
easy_install-2.6 script to
/usr/local/bin
Using
/Library/Python/2.6/site-packages/setuptools-0.6c11-py2.6.egg
Processing dependencies for setuptools
Finished processing dependencies for
setuptools
Não vou especular, mas isso pode ter sido causado por várias alterações no ambiente, como a atualização do Leopard -> Snow Leopard, atualizações do MacPorts ou Fink ou várias atualizações do Google App Engine.