Leona is the reason why Jack enrolled at NRC: when 13-year-old Jack saw Leona playing spelldrive on TV he decided he wanted to play in a game alongside him and, after receiving his acceptance letter, he started training nonstop for the tournament of Book 2.
When Leona is not what he expected Jack asks, “What happened to the man you used to be?,” but as they presumably never met before NRC and Jack would not have known the man that Leona presumably used to be, it is possible that Jack’s frustration came from Leona being different from the assumptions Jack built up in his head after seeing him on TV (Leona: “Your dreams got nothing to do with me!”).
In Book 7 Ace observes, “With great power comes a whole bunch of people pinning totally unasked-for hopes and fears on you.” He was discussing Malleus at the time, and it is possible a point that the two princes have in common.
When Jack stands up to Leona early in Book 2, calling out the “disgusting spectacle” that is the practice spelldrive match against Cater, Ace, Deuce and Grim, Leona responds, “Pretty bold, frosh. I guess I can respect that,” and relents.
When Jack betrays Leona, Ruggie and the entire dorm in Book 2 Leona calls him a “filthy traitor,” which may have effected Jack more than he lets on until Book 7: Jack’s dream seems to be of a recreation of the interdorm spelldrive tournament where a dream version of Leona emphasizes the importance of skill, teamwork, and “hearts burning with drive!,” while Jack joins the chant of, “Long live the king!”
(Azul: “I’ve suddenly developed a much fuller appreciation for how terrifying Malleus’s signature spell is.”)
The dream-infiltration group reflects on the situation Jack faced in Book 2, with Silver explaining, “Turning against the housewarden of your own dorm…not to mention someone you admire…considering Jack had only just started school at Night Raven, that must have taken a lot of determination for him,” and Ortho commenting on the “heavy mental toll” the situation must have taken on Jack.
The group struggles with how to awaken Jack as Jack’s admiration of Leona being reflected in the dream meant that Leona was made even stronger than he is in reality.
Dream-Leona still calls Jack out for having poor technical skills, but he also goes to Sebek’s aid after he ends up outside the playing field, saying, “You don’t have any of the skill or moves it takes to be a back fielder. But you still never slowed down. That takes some serious guts,” and helping him to his feet. (Jack: “Leona’s respectful even of his competitors. That’s incredible.”)
Idia observes, “this dream’s probably changed (Leona) into someone worthy of Jack’s genuine respect…he hasn’t turned into a saint or anything, but he does value sportsmanship and never goes for dirty plays.”
After Jack awakens he reveals the extent of emotional damage, saying, “I wanted so desperately to make you guys realize that. But I couldn’t do anything by myself. That’s why I… I… *sniff*,” possibly in reference to betraying Leona and their dorm.
Jack is not pleased by students of darkness referring to Leona as their king in Leona’s dream (“Leona ain’t your king. He’s our housewarden!”), and it is Jack who awakens Leona by telling him to remember who he is in possible character development for Jack, who had such an issue with Leona being who he is back in Book 2 (“What happened to the man you used to be?”).
After Leona escapes the abyss Jack begins to cry, saying that, while Leona and Ruggie are both still jerks, he prefers the real them over fakes,” and he is “so glad (they) woke up.”
Jack’s respect for Leona comes up often in the game, with Jack saying in a vignette that he has learned they “have one incredible housewarden,” that Leona is “the real deal after all. I knew he wouldn’t let me down!,” and that, while he might play dirty, he is “a brilliant playmaker.”
Jack has a voice line of, “I’m always impressed when I see Leona leading my dormmates. I gotta catch up to him, quick,” and when Deuce is impressed by Leona’s willingness to help others during Vargas Camp Jack responds, “Leona being amazing is no surprise…I can definitely look up to a guy like Leona!”
Jack is reluctant to ask for Leona’s help during the lantern event and embarrassing himself. When Kalim says, “I’m sure he’d help and be all cool about it, like, ‘No worries. We gotta look out for each other, right?,’ Jack says, “I don’t think he’d say ANY of that.” When Riddle follows with, “This is Leona we’re talking about…he’s more likely to ask how we’re struggling so much with not one but TWO housewardens present,” Jack responds, “That sounds more like him.”
Leona does go to the aid of the library-trapped group. Jack says, “I appreciate you coming to help, but I really didn’t want you to see me like this…” and thanks Leona for bringing over one of his personal belongings (his chessboard) to help them.
When a visitor during Port Fest accuses Ruggie and Jack himself of stealing his wallet Jack does not seem particularly bothered, but when the visitors insinuates that Leona was also involved Jack takes offense (Leona: “Put your fangs away, Jack”).
When Vil scolds Jack for not knowing how to wear his ceremonial robes properly he says, “What has your housewarden been teaching you?,” and Jack responds, “He’s got nothin’ to do with this.”
Jack seems pleased when Leona compliments his idea for Halloween, and even moreso when he compliments Jack’s successful strategy for scaring off Magicam Monsters. When Leona compliments him at the conclusion of Port Fest, Jack is left momentarily speechless.
On EN Leona’s issue with Jack was rewritten as, “Tch. Stupid frosh…talkin’ like he’s better than me,” but that was not actually Leona’s problem with Jack at all: his problem was Jack reminding him of his older brother, but both references to Falena were removed from Book 2 of the EN game.
During Port Fest Jack tells Leona, “if the other dorms run their mouths, I’ll deal with ’em! I won’t make you look bad, Leona!,” but there are multiple instances of Jack himself disparaging Leona behind his back: he calls Leona lazy and irritable in a voice line, calls him a coward when speaking to Riddle, and says that Riddle “isn’t scared of puttin’ in some effort to get ahead. Again, unlike you-know-who.”
Jack is one of many people who struggles to understand Leona, frustrated with what he perceives as Leona’s refusal to use or hone his incredible power and talent.
Jack seems surprised when Leona does not get caught in the drama of Book 3, apparently unaware that Leona does not have any need for Azul’s study guides: Leona explains,
“I had my own private tutors from an early age, with a curriculum way more advanced than I’d have had in school. I don’t know what I know ’cause I’m always hittin’ the books like (Riddle). I just already know it.”
When Jack insults Leona to his face he will apologize, such as during Book 3 (“I figured you’d go for the easiest out of you could get, Leona… Ah, no offense, of course”), and at the start of the Cloudcalling event when Leona reveals he is expected to teach “rules and best practices for guarding king and country. Even etiquette,” and Jack, along with everyone else, laughs aloud (“Hahaha… Oh! Uh, sorry, Leona”).
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.”
Leona also refuses Jack’s offer of a competition during another New Year: Jack insists on enlisting Leona in a tako battle and when Leona asks why, Jack responds, “Because it’s a rare opportunity to go head-to-head with you! You’ve got good instincts, so you’ll probably pick up how to play pretty quick and put up a tough fight. And I wanna see how well I can hold my own against someone that good!”
Leona refuses until both Jack and Ruggie pressure him together, but Jack is disappointed when Leona loses almost immediately. When Leona looks pleased Jack suspects that he threw the competition on purpose, which Leona confirms.
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).
Leona’s dorm vignette revolves around an incident from early in the school year where Jack takes issue with upperclassmen skirting the rules on the spelldrive field. In what is possibly their first conversation since Jack enrolled, Leona says, “I’ve heard about you. Rumors say you’re a real promising athlete, even as a freshman.”
Jack insists that he is only playing fair and everyone else is “hitting below the belt” because they can’t take him in a fair fight but Leona says, “I fail to see the problem. Playing smart to win a game is just common sense.”
Jack is shocked by Leona insinuating that he will “let these dirty cheaters off the hook” and Leona points out,
“You said they were ‘skirting the rules,’ which means they’re still legal. There’s nothin’ cowardly about it. That’s a legit tactic. Rule-wise, they’re not causing any problems. YOU, on the other hand, are being disruptive to the team. That’s a problem for the dorm.”
When Jack is out of earshot, however, Leona turns on the upperclassmen who had been harassing him, saying, “Don’t get all huffy just ’cause you’re losin’ to a frosh. It’s embarrassing to watch,” as though agreeing with Jack that they were only frustrated with their inability to beat him in a fair fight.
Later Leona overhears the same upperclassmen planning to “knock Jack down a peg,” and even Ruggie recommends that they let the other students “put a little fear into lack and teach him to respect the rest of his dorm.”
The upperclassmen confront a lone Jack with thirty other students with Leona intervening once they begin to use magic in the brawl:
“If all you were doing was roughing Jack up, I was gonna write it off as rough play and let it go…You’ve got a whole squad here and you STILL came out lookin’ like fools. None of you have what it takes to lead a pack.”
The students decide to turn on Leona instead and Jack tries to tell Leona that this is not his fight, but Leona orders Jack to stand down: “Thirty mice still ain’t a match for one lion.”
Leona deflects every spell that is cast at him (“We can’t possibly be this outmatched!”) and then begins to invoke his unique magic, only stopped once Ruggie intervenes, pointing out that the students have al “passed out from sheer terror.”
Jack asks why Leona came to his rescue and Leona responds, “Babysitting a pup that ain’t even opened its eyes yet is part of the housewarden job description,” calling Jack “a brat who doesn’t follow orders and runs off half-cocked. But at least you’re not so thick as to fail to learn something from this. At least I hope not.”
Jack apologizes for causing trouble and thanks Leona for his help, saying that he has learned some valuable things: “Like that I’m still green in so many ways….And that we have one incredible housewarden.”
Leona responds, “guys who own up to their mistakes are all right in my book. Keep at it and model that behavior for the rest of Savanaclaw, wouldja?”
Although Jack might never know it Leona protected him from Ruggie in Book 2, when Ruggie offers to “take care of (Jack)” before he becomes a problem, and Leona tells him no.
During Halloween Leona decides to get refreshments for the students of Savanclaw (Kalim: “I know Jack’s been working hard as part of the management committee”), downplaying himself with, “I’m lucky their brains are in their stomachs. Makes payroll as simple as can be.” Ruggie responds, “Can’t you just admit you wanna do something nice?”
Leona stands up for Jack later during the Halloween event, refusing to take command from Jack despite how his dorm members look to him for leadership: “Jack, you’re callin’ the shots. We’ll be following your plan.”
When the kidnapped Jack reunites with Leona and Ruggie towards the end of Spectral Soiree Leona greets him with, “If it isn’t the little lost pup who scampered out the door. Did you remember where your house was?” Ruggie whispers, “C’mon, Leona. Would it kill you to be honest with the guy and tell him you were worried?”
Leona agrees to enter Playfulland in order to chaperone Jack, joining Jack when the students separate into different groups.
Twisted Wonderland Reference Note 