Their current strategy seems to be based on three observations:
1. There are a lot of Windows users in the world and Ruby sucks on Windows.
2. There are a lot of existing companies using Java still and many are scared of Ruby.
3. Even if people get past 1 & 2 a lot of people are still scared off because "Ruby/Rails Doesn't Scale" (i.e., MRI is slow).
They are executing against all three of these barriers with their various initiatives:
1. Make Ruby a better platform on Windows: Rails Installer, SQL Server ActiveRecord adapter and including Windows as a target platform for their VMs.
2. JRuby as a gateway drug to the Land of Ruby; _could_ end up being VM winner too.
3. Rubinius as a possible MRI replacement, if they can make it technically superior and rally support within the community. (Think Merb -> Rails 3)
With this in mind, it makes perfect sense for them to support both JRuby and Rubinius.
It also makes sense for them to not be too overt about at least some of these goals. (See Merb vs Rails compared to SlimGems vs RubyGems.)