Ruggie and Jack meet for the first time when Ruggie gives an impromptu tour of the school’s clubs that Jack and Epel join.
Ruggie promotes the Spelldrive club in particular in an effort to get Jack to sign up but approaches it from the perspective of teamwork, of which Jack is not a fan.
Ruggie says, “every time I see him play Spelldrive at Savanaclaw’s morning practice, it reminds me of the one that got away”.
Ruggie considers Jack to be a snitching “goody-two-shoes” (and Jack openly announces he will be reporting Ruggie’s “dishonesty” during Vargas Camp), and during Halloween we see him having to convince Jack to break the school’s “no using magic on laypeople” rule to chase off Magicam Monsters.
Ruggie teases Jack for “heroically standing up for the downtrodden” when Leona and Ruggie play against Ace, Deuce and the others in a practice game of Spelldrive during Book 2, and expresses frustration at Jack’s attitude, saying, “the world’s not black and white. Not everything can be categorized as ‘right’ or ‘wrong’. Too bad he can’t be more flexible, huh?’.
Jack seems to be taking Ruggie’s efforts to heart: in a voice line he says he might be looking to start aspiring “to be like Ruggie and not sweat the little things. But don’t tell him I said that!” and, during Vargas Camp, we see Jack successfully convince Ruggie to join a search in the mines for Deuce by tempting him with magestones.