I looked at the problem of having two JRubyXStreamConverter loaded.
I couldn't reproduce the issue locally, but the failure mode made me 
suspect that you made some change in the Jenkins core, and in particular 
added jruby-xstream as a dependency there. That would cause jenkins.war 
to have its own copy of the jar, and then your plugin would get another 
copy, so you can end up in the situation where you indeed have two jars.
I intend to make some change in the playground to show you how you can 
register JRuby converter to Items.XSTREAM without adding any dependency 
to core. Hopefully that'll unblock you.
-- 
Kohsuke Kawaguchi | CloudBees, Inc. | http://cloudbees.com/