During Firelit Sky Trey expresses gratitude that they don’t have to worry about getting robbed at school and Jamil says that he has “heard rumors of a hyaena on campus with sticky fingers”.
Trey and Grim are both unsurprised, possibly insinuating that Ruggie is maybe well known for his pickpocketing skills.
In Book 2 Ruggie steals Cater and Riddle’s magical pens out of their pockets without their noticing, and in Book 3 he steals the key to Azul’s vault. Leona says, “your compulsive pickpocketing never ceases to amaze me.”
In Book 5 Ruggie refers to the VDC’s guests as “easy marks,” and his pickpocketing is a significant part of Fairy Gala where Leona selects him to join the event in order to swap out the Fairy Queen’s real tiara with a fake one without the use of magic.
Ruggie says that he will need fifteen seconds, which Leona cuts down to ten. In the end Ruggie requires only six seconds to perform the swap, saying, “Who needs ten seconds? You insult me, Leona.”
Ruggie also mentions “swiping” food before it was thrown away at a restaurant where he used to work, and at the end of Vargas Camp it is insinuated Ruggie had been intending to keep the necklace that Leona lost towards the beginning of the event, though he insists that he had just been holding onto it and had been intending to give it back all along.
Ruggie also hints at wanting to steal from Leona in Book 2 and Rook says he saw Ruggie stealing candy from people in a Halloween voice line.