We can sit here and ping each other with examples of cruft all day. I think it can be shown objectively that Python's standard library is better maintained. I'll attempt to below.
I'm not saying this has a great significance in picking one language over the other in and of itself. Just that if you want to talk specifically about stdlibs, the differences are pretty clear-cut imo.
== In terms of quantity of updates ==
- Mar 13 2007: Ruby 1.8.6 launched
- May 18 2008: Ruby 1.8.7 launched
- Distance: ~14 months
- Sep 19 2006 Python 2.5 launched
- Oct 18 2008 Python 2.6 launched
- Distance: ~23 months
So discount the amount of 2.5->2.6 changes accordingly to account for the extra time.
Then compare stdlib changes:
- Ruby: http://svn.ruby-lang.org/repos/ruby/tags/v1_8_7/NEWS
- Python: http://docs.python.org/whatsnew/2.6.html#new-and-improved-mo... or http://www.python.org/download/releases/2.6.1/NEWS.txt
== In terms of quality of documentation ==
Compare
http://www.rubydoc.info/docs/ruby-stdlib to http://docs.python.org/library/
You'd need to compare across actual libraries (unittest vs Test/Unit etc). I didn't provide specific examples in links to avoid inevitable accusations of cherry-picking.
== In terms of process ==
Compare http://www.python.org/dev/peps/pep-3108/ to... closest equivalent I could find was http://redmine.ruby-lang.org/projects/roadmap/ruby-19 . Anyone with a better link?