alright a long time later I finally figured it out. Turns out winstone was not the issue, but rather file permissions were to blame. Some of the files in my jenkins folder /var/lib/jenkins/ had root as their owner rather than jenkins. There were some in .m2 some in .grails and just scattered all about, not sure how this happened.
Anyway I just navigated to the home dir of jenkins /var/lib/jenkins and ran the following command
chown -R jenkins:jenkins jenkins