Kifaji is introduced as “the grand chamberlain of the royal family” and seems to have been a large part of Leona’s childhood: when Kifaji asks how it is that Leona ended up “so horribly twisted” Leona responds, “probably ’cause some twisted chamberlain was always givin’ me a hard time.”
Kifaji reflects, “To think that cute little boy who threw tantrums when I beat him at chess would grow up to spit such poison from his mouth. Perhaps I was too hard on you after all.”
Leona says that, while Kifaji has always been a nag, he “makes a decent chess opponent.” When Kifaji calls Leona out on a strategy during the tournament of the Cloudcalling event Leona says, “In chess it’s perfectly legitimate to go for a draw.Seem to remember some dodderin’ fool teachin’ me that in my youth.”
Kifaji responds, “Was it a warm and kind chamberlain, perhaps? How lucky you were to have such a person in your life.”
It seems that Leona and Kifaji also play pool together, and Kifaji taught him everything he knows about flying (Leona: “Whether I wanted him to or not”).
While not mentioning Kifaji by name Leona says that, when he was a child, his caretakers would always try to sing him to sleep with “some preachy lullaby about the world bein’ a small place.”
During Cloudcalling Kifaji describes a candy that Leona seems to have liked since when he was a child.
Leona says that the Kifaji of his dream acting friendly weirds him out: “Normally you yell at me when I skip out on my duties and threaten all sorts of punishments. You’ve always been like that-rearing any prince into a proper model of royalty. Even the one not in direct line of succession.”
Leona and Kifaji spend a significant part of the Cloudcalling event bickering with one another, but when Kalim tells them they shouldn’t fight Lilia intervenes, observing, “They’ve been acting like this the whole time. They’re probably always like this.”
It is Kifaji who calls Leona home for the Cloudcalling event, threatening to go to NRC directly to fetch him with “all the other chamberlains” unless he complies.
Leona does not seem to appreciate Kifaji being “so hung up on those dusty old traditions.”
After Leona returns home Kifaji reminds him that one of his responsibilities as grand chamberlain is preventing predicaments that will cause Prince Falena hardships, asking Leona to avoid causing his brother “any undue trouble.”
Leona greets Kifaji upon his arrival by questioning his good timing, saying, “You mean you wanted to make sure l’d actually come back. Don’t trust me at all, do you,” and Kifaji responds, “I wonder in truth which of us it is who does not trust the other?”
Kifaji says he is shocked that Leona brought others with him to attend the festival as he hadn’t imagined that Leona was forming friendships with others at the school. (Vil: “Are we actually that good of friends with Leona?”)
Leona is not pleased by the revelation that Kifaji intends to attend to them the entire day, returning to the palace for the explicit purpose of getting a car that will not seat enough people to allow Kifaji to join them to Ivory Spring. (Kifaji: “I must say, that was rather clever.”)
During the Cloudcalling event it is revealed that Kifaji himself trained Cheka’s attendants for the tournament, to Leona’s surprise, and that Kifaji never informed him of a new rule allowing for athlete substations (Jack: “He’s really got it in for you…”)
Despite such setbacks, Leona manages to win the tournament anyway, with Kifaji saying, “Such overwhelming strength…well done, Prince Leona. Ever since you were little, you’ve been surprising me at every turn. Sunset Savanna’s future should certainly be entertaining.”
Twisted Wonderland Reference Note 