Leona says that one of the things he likes about chess is being able to get an idea of what is going on inside an opponent’s head, and this might connect to his dislike of Malleus: there are comments from several characters throughout the game saying that they cannot tell what Malleus is thinking.
Leona’s dislike of Malleus is established early in his ceremonial robes vignette when he tries to refuse a conversation with Silver by saying he has nothing to say “to Malleus’ cronies.” Silver says that he seems them speaking together frequently, to the point that he thought they were friends (Ruggie: “Uh, not sure I would call that ‘speaking.’ Try ‘clawing at each other’s throats’.”)
Leona ends up with Malleus’ ceremonial robes on accident and, after bringing them to Diasomnia, Silver interprets the visit as Leona wishing to “have a heart-to-heart” with Malleus, and they must be friends after all. (Leona: “I’d much rather deal with Malleus. At least his ears ain’t just for show!”)
Upon being presented to Malleus Leona comments on Diasomnia being “stuffy” and “irritable,” but when Sebek orders him to “silence that foul mouth” Malleus scolds him, saying, “Royalty is owed respect.”
Upon receiving his own robes (that Malleus had tried on) Leona says they “smell like lizard,” once again earning him a reprimand from Sebek who is once again told to stand down by Malleus who says that it is his duty as royalty to thank Leona for his effort.
Leona responds, “Is that what you think you are? Just a high-and-mighty royal? More like an outcast who’s been chased from his pack. I feel sorry for you,” and possibly realizing that not being invited to the opening ceremonies is a delicate subject for Malleus he continues with, “sorry to break it to you, but no one’s ever gonna invite you,” successfully goading Malleus into insulting him back.
Observing their back-and-forth from the side Ruggie comments, “Maybe Malleus is more normal than I thought,” while Lilia is delighted by Malleus having the opportunity to enjoy “a bit of ribbing” with a schoolmate (as the only other royalty at the school whom we know of, outside of Silver, Leona is possibly the closest thing Malleus has to an equal).
The drama of Book 2 begins with Crowley emphasizing how Savanaclaw’s students have been having their future careers compromised ever since Leona became housewarden due to Malleus’ participation in spelldrive games.
Leona is not amused, and we are given more information in the novel adaptation:
Leona’s words resonate with their hearts, with their minds. That unbearable humiliation resurfaces within the chests of all who hear him.
Twst the second novel (fan translation)
When Malleus had beat them all, he had faced the television cameras with a tilt of his head but no particular joy, as though to say, ‘Is that all?’ Riddle and the others had watched with bitterness, and a slight sense of fear. No amount of talent could prevail before him, and he had not allowed even one person the slightest opportunity to show what they could do.
How they had been on the ground, helpless before the storm of Malleus’ magical power had been etched into the memories of people worldwide.
It is impossible to count how many times they grit their teeth in response to hearing, yet again, how even students from the prestigious Night Raven College cannot compete against natural-born talent.
This cannot go on.
Leona initially refuses to participate in the interdorm tournament (though Savanaclaw possibly would have been disqualified for the stampede and the decision was not his to make) as they will not be able to win if Malleus joins, and he is proven correct.
At the end Leona asks, “Remorse? Who says I gotta have remorse?,” and prior to the battle of Book 7 Ruggie asks, “Do we finally get to see what we never saw at the spelldrive tournament? Do we get to see a beaten-up Malleus Draconia kneeling before Leona?” (Jack: “You guys still haven’t given up on that…?”)
Twisted Wonderland Reference Note 