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!”
When Leona goes to the aid of the library-trapped group during the lantern event (which includes Jack), 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 Maficam 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”).
Twisted Wonderland Reference Note 