I sketched this up in sketcher on www.artgrounds.com
Jack is obviously drunk therefore his mind isn't stoping him from blurting whatever comes to it out. Not that anything has ever stopped him from blurting comments out before but yeah...
Captain Finch appears very amused by this and probably supplied said rum to him to entertain herself with his antics.
My question is..what is he saying exactly? Type in the comments what you think it is and on June 17th I will chose the one I like best edit the speach bubble and the person with the clever mind gets a free sketch of their character, savvy?