Ruggie appears, panicking over a necklace of Leona’s that has been stolen by a crow, and Jack vows to “finally be of use” to him.
Jack ditches an entire day of school in order to find the necklace, returning it and lying to Leona to protect Ruggie.
Jack reveals that he used no magic to find it and instead climbed every tree in the school, checking crows’ nests throughout the night until he found it.
Ruggie immediately suspects Jack of wanting to extort him for a finder’s fee, telling Jack outright, “I can’t trust you”. For compensation, Jack asks if they could enter into an older/younger brother relationship, but Ruggie turns him down, saying that Jack is closer to a minion.
Jack says that he should’ve known that Ruggie wouldn’t make it easy for him, but, “Someday, I WILL earn your respect!” Even so, Jack has a voice line of “Ruggie has a way of gettin’ me to do stuff without me even realizin’ it. It’s irritating.’
Jack does not enjoy being told what to do, and during Beanfest Ruggie claims that there is no point in him trying to give Jack orders because he’s both stubborn and stronger.
Despite this we do see Ruggie giving Jack instructions in other scenes, and Jack obeying without complaint.
When Ruggie experiences no issues with the dream-jumping in Book 7 it is Jack who explains, “He’s the best in the game at tricky flight maneuvers. Never underestimate his aerial chops!” Grim asks, “Why’re you bragging about it, Jack…?”