I know the debugger gem is not and never will be compatible with ruby 2.0 per "officially support ruby 2.X".
In the changelog of Ruby 2.0 is:
Version 1.4.0 of the debugger gem now installs without problems. There are still some issues but this should be fixed soon.
The debugger gem does not play well with Ruby 2. Instead, install the Byebug gem that is fully compatible with Ruby 2.