If you got "brainwashed" in the last 5 years about code quality (DRY etc.) + test methods (TDD/BDD) and then look at today's Stdlib, you'll scream and want to put bleach into your eyes…
To me it seems the "übercool" guys already moved away to their NoSQL/node.js/whatever next party, so it's not easy to motivate people to change such "messy" and large projects anymore.
I'm also not sure about the number of Ruby interpreters around and their useful impact: If you e.g. change something for Ruby 1.9.x / 2.0.0, it will cost a lot of manpower to port those changes to JRuby, Rubinius, maglev, IronRuby and BlueRuby (if SAP's Ruby is still alive?) and most of them are just used by very few people.
Maybe resources are better spent in creating a new Stdlib, improve the rubygems infrastructure (already started with gemcutter) and do something with RAA?