Leona says that Jack is “pretty self-aware,” saying he can get prideful but knows he’s not boss material yet, “So he always follows the boss’s orders when push comes to shove,” and we see several examples of this in the game:
When Leona tries to recruit Jack for the Fairy Gala IF event Jack initially refuses (“There’s nothing I hate more than gettin’ chummy with others”) until Leona explains,
“What we need is someone who can lead the pack. Someone with solid judgment and initiative. I figured you had both of those things…there are a lotta students in Savanaclaw, but I picked YOU…I’ll have to find some other freshmen. Sorry for expectin’ more out of you.”
Jack then agrees to join.
Leona has Jack round up Lilia and Vil to explain the situation of the Cloudcalling tournament, with Jack immediately willing to participate.
When Jack faints from heatstroke, Leona takes responsibility for not warning him about the heat (Grim: “L-Leona just admitted he made a mistake!”).
Jack and Leona seem to get along well during Playfulland, coming together to demand that Kalim delete photos of them riding a carousel and to become very quiet when Kalim refers to them as his friends.
Leona initially refuses to do the “hanetsuki challenge” of New Year’s despite having spent enough money to be eligible, only reluctantly acquiescing when Jack says, “I’m asking you to do this one—for me.”
When Ruggie refers to Leona as someone Jack admires in an early vignette Jack responds, “I’m not sure l’d say l ‘admire’ him. I do wanna surpass Leona one day…,” but this seems to have changed by Port Fest, where Rook encourages Jack to speak to someone he deeply respects and admires, and Jack goes to Leona.
Leona is not pleased about Ruggie and Jack being the instigators behind the entire Port Fest event, saying, “Normally you four makin’ fools of yourselves on that stage would be fine by me. Problem is, there are TWO Savanaclaw in your little band. I can’t have the other dorms callin’ us a laughingstock.”
Jack insists that he will perform even if he has to do so alone, he won’t make Leona look bad and will deal with any other dorms who “run their mouths” (Leona: “Bold of you to say. But reckless”).
When Jack is at a loss of what to do Leona asks, “You just do everythin’ Crowley says, no questions asked?,” and encourages him to identify his prey: What’s out there just beggin’ for you to sink your fangs into it?”
Leona refuses to explain any further and Jack confers with Ruggie (“You went to LEONA about it?! Talk about desperate measures”), who suggests that they reframe the situation: “What if we think of it as a show FOR Leona?” (Jack: “Uh… I think that makes it even harder.”)
They imagine a show with Leona in the audience where he is most displeased with their performance, but imagining his reaction to them substituting themselves with the pop music club is no better.
Jack comes up with a solution on his own (“It’ll impress Leona AND the Port Fest attendees!”), saying that he has found their prey.
Jack thanks Leona for giving him the advice that inspired him but Leona responds, “I didn’t do nothin’.”
At the end of the show Leona says that Jack’s idea was “pretty ingenious,” but to Jack himself he says, “You managed to hold my interest all the way to the end. Not half bad.” (This is enough for Jack to be rendered momentarily speechless).
Twisted Wonderland Reference Note 