As the only “education” that Ruggie received prior to NRC was in “practical life skills” he struggled in his classes until Leona started providing him with reference books, old exams and advice.
Ruggie says that his grades are now a solid “middling” and it is “a pretty huge deal” for someone to work their way up from the bottom to “somewhere just below the middle”, and “the moral of this story is to stick close to the biggest fish in the pond, and figure out how to make it benefit ya personally”.
Leona seems aware of the fact that he is being used in this way and says that Ruggie’s shamelessness is his strength. He calls Ruggie’s magic “underwhelming” and “barely worth mentioning,” but explains, “Thing is, he knows it. So he sucks up to me and uses me. That’s not bad or something to be ashamed of.”
Leona says that while Ruggie is nimble, a smooth talker, cautious and can handle anything by himself, his problem is he is “practically programmed to think like an underdog lackey”, and needs to approach his problems from a pack leader’s perspective. We see Ruggie take this advice in his dorm vignette where he employs Lucius to handle a problem he had been having on his behalf.
This comes up again in Vargas Camp, where Ruggie’s initial reaction to the Vargas Monster is for everyone to split up and run in different directions, as his top priority is survival. When Sebek and Jack refuse, Ruggie comes up with a plan that incorporates everyone’s skills and ultimately saves their clubs from being disbanded.
We see Ruggie reminding Leona to attend classes and meetings. Leona says that there are classes he cannot skip because Ruggie will not let him, and if the prefect needs help from him they need to go to Ruggie first, who will pass on the message to him if Ruggie decides it is actually necessary to do so.
Ruggie seems free to refuse tasks from Leona that he does not wish to perform, such as passing on messages from Crowley to Malleus. A reluctant Leona concedes to Ruggie’s wish to stay at Diasomna for Lilia’s farewell party for the free food.
(Lilia: “A soldier who can still eat his fill when standing in an enemy camp is a formidable one indeed. – Ruggie: “Hey, pride doesn’t fill an empty belly. Lilia, I’m happy to take you up on that!”)
Ruggie also refuses to help save Leona or Jack from Eliza during the Phantom Bride event, saying that Leona will find his way back on his own.
Twisted Wonderland Reference Note 