honestly, i think ruggie has some unexamined abandonment issues lol. he seems so flippant and mischievous, laughing off any trouble and teasing others without a care in the world. this is a part of him and what he enjoys, that's true, but the carefree demeanor and humor are also a coping mechanism.
he keeps people at a certain distance! it's why he doesn't call people his friends. he doesn't like to initiate things and prefers following rather than leading because then if it blows up, it's not his fault. and he's also calculating enough to throw his lot in with the people who can give him the resources he lacks. he knows what he's missing, and seeks it out in others!
ruggie also always has one foot out the door. he's cunning, and though he has hope, he's also too jaded to really throw himself whole-heartedly into a scheme unless the promise of a reward is guaranteed. stick with the person who'll help you survive, and then jump ship when it's not working out to the next person who can give you what you need.
trust is extremely difficult for him, though i think once earned, he never lets go. he takes care of his own, even at the expense of others. it's a very us vs them mentality that he doesn't shake, because he believes the world is a rigid dichotomy of give or take. so either you're on his side, or you're not. he's using you, or he's being used. it's comforting if he can ascribe things to such simple logic rather than rely on something as unpractical and fickle as sentiment. never give someone the power to hurt you!!