In a vignette we see Ruggie wishing he could grow taller while bemoaning his inability to afford any additional eating expenses.
It is not confirmed how much Leona overheard, but he then gives Ruggie his entire wallet to go buy laundry detergent, saying, “I’ve got plenty in there. Take what you need and keep the change.”
Ruggie responds, “All you’ve got in here are big bills. You really want me to break one of these?,” and, “He wouldn’t even notice if I kept more in change than what the detergent cost, I bet,” seemingly unaware that that might be Leona’s exact intention: we have seen Ruggie decline money and favors from people in the past, and it is possible that Leona has realized that Ruggie will only allow someone to support him financially in exchange for labor or if he feels like he is getting away with something.
(Grim: “I woulda thought that Ruggie’d be like, ‘Sweet!’ if you offered to do stuff for him. What gives?”)
We have seen multiple instances of Ruggie seeming to have free reign with Leona’s wallet, such as during New Year (Leona: “And you can buy whatever else you want while you’re here”) and when visiting the school store alone.
It is possible that Leona had intended to overlook Ruggie smuggling magestones out of Vargas Camp to sell later on, only having him give them up at the end of the event in order to battle a mine monster.
Ruggie seems free to accept or refuse tasks from Leona as he wishes: Silver guesses that Leona approaches Malleus personally in a vignette only because Ruggie has said no, and Ruggie says that Leona tried to get him to go to the school store alone during Halloween but he insisted on taking Leona with him.
Ruggie also overrides Leona’s refusal to let Grim and the prefect stay over in Savanaclaw in Book 3, even offering them Leona’s own bedroom, and when Leona tries to leave Lilia’s farewell party early Ruggie argues against abandoning an opportunity for free food until he acquiesces.
In a voice line Ruggie invites the prefect to a Savanaclaw dorm meeting, saying, “Depends on what Leona says. The trick is in how you ask.”
Ruggie also shows the Fairy Gala group how to get into Leona’s bedroom when the door is locked,
During Halloween Ruggie is approached by campus visitors for a photo and decides to redirect them onto Leona, saying, “If you want a pic with someone who’ll blow up on Magicam, I know someone way better than me. He’s buff and tough, AND he’s from a royal bloodline…” only to realize that Leona has already left him behind.
Ruggie says, “You can’t just ditch me…Don’t use me as a decoy just because you can’t be bothered to talk to people!,” but Leona responds, “You were about to use ME as a decoy. Turnabout’s fair play.”
Twisted Wonderland Reference Note 