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.
Ruggie prepares an almost-empty backpack to take to Fleur City for the purpose of bringing “lots of stuff” back with him. Leona says, “All l ask is that you only bring back things you got through legitimate means.”
Ruggie is delighted by the discovery of a hat full of coins in Fleur City, saying, “Someone lost this! Wouldn’t it be best if I picked it up?” Idia responds, “Somehow I doubt it’d make it back to its owner.”
Silver assures an unamused Rollo that Ruggie was intending to return the hat and Rollo explains that the people in the town have recently formed a city watch for tourist seasons. Ruggie says, “Good thing you told me all this now.”
After Jamil and Ruggie get cut off from the rest of the NRC group Jamil says that he is glad that he is with Ruggie rather than someone else, asking if Ruggie would not be adverse to dirty tricks.
Ruggie says, “You’re gonna take advantage of the chaos and swipe some valuables from the college!,” and Jamil responds, “We’re drowning in firelotuses and all you can think of is money?”
Ruggie is accused of stealing a wallet during Port Fest, and neither Leona nor Jack go to his defense.
The wallet is discovered to have been in the lost and found before Ruggie and the festival attendee even overlapped, and Ruggie insists on the the attendee purchasing multiple waffles from his food stall in compensation.