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First thing’s first! From the game, we know that Leona enrolled in Night Raven College one year late (and then got held back a year, which makes sense considering he is 20 in the main story present). He didn't find a use in attending school since he, by royal birth, was able to afford all the best tutors in the world and didn't think NRC had anything left to teach him. In Leona's Birthday Boy vignettes, he further specifies that he decided to enroll at NRC after Cheka was born. As Leona says in his post-OB flashback in-game, Cheka's birth means "the despised second son loses what little claim he had to the throne forever", essentially putting an end to his hopes. This would imply that this specific change in circumstance was the push that made Leona want to physically distance himself from home. Furthermore, it's supported by Leona's other behaviors: he does not take calls or read letters from home if he can help it (implied by Cheka asking why Leona doesn't answer his letters and Cheka calling on Halloween night to catch up with him; Leona lies and quickly hangs up), he makes excuses to avoid going home (as Kifaji states), etc. If we want to extrapolate even more, how is it that Leona, second born prince, initially crossed paths with Ruggie, who was born and raised in the slums (which, I imagine, must be quite some distance away from the royal palace)? This makes me think that even before Leona enrolled at NRC he would leave his housing and roam around, finding alternative places to stay because home just felt too uncomfortable and suffocating for him. There's also the implication that Leona often brooded over his circumstances, as he confesses to thinking about it and going to NRC to get his mind away from the tired cycle--although he also acknowledges that he's running away from "the pain" of having lost the throne.

The distancing would prove itself to be beneficial to his mental health, as Leona cites that his heart started feeling lighter, his restlessness dulled, and his pain numbed. With the throne out of sight, so, too, was it out of mind, and his longing softened. But that same haunting despair returns when another group starts to place expectations on him. This time, it's no longer the palace servants, but his own dorm members. Instead of fear and derision, his new pack looks at him, their "king", with desperateness--and, more importantly, hope. Speaking about the future with sparkling eyes. That, in turn, made Leona hopeful too. He can't let these people who look up to him and rely on him down, so he must do anything to win. That's all he ever wanted: to win, just this once. No matter what, he wants to win.

But when Leona's plans crumble, that crushing sense of despair rears its ugly head. He fails. And he suddenly understands that all his efforts will always amount to nothing, that they will always be meaningless, that there is no future for him. Leona's hopes have been dashed. He has been struck down by the world once again, just as he had started to climb up, fighting tooth and nail, to prove himself. Yet when defeat came, he also claims it doesn't bother him as much as he thought he would--perhaps because he's so accustomed to not winning, because maybe this is the outcome he had expected all along in the deepest recesses of his heart. That familiar disappointment begins to hurt him once more, and Leona wants to forget it all, to retreat to the shadows and to lick his wounds, to be far away from that pain.

One interesting new detail we glean from the light novel is that Leona is terrified by his dorm mates staring at him with hopeful eyes. It's not their expectations he's inherently scared of, but what those expectations can do to him. Leona is scared of himself, of being motivated by others to act, to never give up hope, when he still anticipates being beat down again and again by a world that rejects him and denies him. He even goes so far as to say he would be pathetic if he let his dorm mates' words inspire him and keep his waning hope alive. Ruggie, who had wanted to turn the world upside down together. Jack, who was inspired by his play three years back. All the mobs putting faith in their futures on him, their one and only leader. With so many people looking to him, how can he not be swayed by that positivity that had once been so elusive to him? How could that not ignite what little spark of hope is left in him? And that's exactly what Leona finds so dangerous about it. He's lived almost his entire life being put in his place, hurt every time he tried to demonstrate what he could do, how he could contribute--yet time and time again, here comes life, tempting him to try again, just to inevitably be compared to his brother and kicked down, delivering another blow to his pride and his self-image. Leona truly seems to hate himself for not being able to let go of that small fragment of hope he has left. He wants so badly to give up and not have to worry anymore about something he can never obtain. He's so tired of struggling and suffering for nothing. If he just caved, then he would never be hurt again. He can't be hurt if he doesn't care about anything. Yet no matter how much he wishes or tries, he can't run far enough away to detach himself from those expectations of grandeur, of being something more.

There's been many fan theories about Leona's mental health in circulation well before the release of this light novel, many of which mention self-loathing in spite of how proud and confident he typically presents as. You'd have to read in-between the lines of dialogue from the game to draw these clues out, whereas the light novel lays it more bare to you. It hits very differently reading hateful statements made by the character to himself. Leona calls himself all sorts of things: a fool, pathetic, insignificant, boring. That he isn't strong, that he isn't wise, that he's not loved. (In the in-game flashback, Leona also talks in a self-deprecating way, but to a far lesser extent than in the light novel; we also see that Falena does his best to discourage Leona from this kind of behavior.) That this is who he is, that it's the one thing he's afraid to admit and accept--but he also says he lacks the "strength" to give up. That's why Leona would rather run away than confront that potential truth. The option to embrace complete nihilism just isn't possible for him, because he can't just quash that pesky little thing called hope. This is much more complex than what's explained in the games and demonstrates a maturity and degree of self-reflection from Leona that we've never seen before. What's more, this gives us brand new context with which to view many of his other seemingly mundane actions mentioned in the game. At face value, Leona often acts very callously and doesn't care to help others unless he gets some kind of benefit from it (like agreeing to poof the contracts in book 3 just because he has his own deal he wants to get rid of). We see this time and time again when he instructs others reliant on him or less knowledgeable than he is in various matters where he is well-read and experienced with. For example, he takes note of his club members' strengths and weaknesses and offers tailored advice to help them improve their play. He tells others how to mine magestones of an adequate size in Vargas Camp. Maybe he's just doing these things to make the circumstances easier for himself (so he can put forth less effort to leading them in a game, or so he can nap heartily). But from what we've just learned from the light novel, now I'm suspecting a different secondary motive.

What if... Leona is, in part, encouraging and helping others to hone their own skills to subconsciously compensate for what he doesn't believe he himself is capable of? Because there's still so much hope for his dorm mates, for his underclassmen... (and, let's not forget, it was those in Savanaclaw that first motivated Leona to "try" again for the first time in forever) but he doesn't have that same amount of hope for himself. I get these vibes as late as book 6, when Leona and Jamil have a talk. In their conversation, Leona directs many pointed, blunt words at Jamil--words that could very easily also be thrown back at Leona's face and be applicable to his book 2 self. He accuses Jamil of making excuses so he won't have to actually act, just as Leona has continuously run away from uncomfortable situations to put himself at ease. At one point, I believe Leona event states that Jamil “*isn’t like [me]”, Here, again, it can be argued that we're seeing Leona's self-awareness on display, as well as a willingness to warn others to not follow down the same path he once treaded, to lose all hope in the future. Again, it's done with a double purpose: the other one being to get Jamil out of his way while they're exploring. And (of course) Leona's way of expressing his message is gruff and not very warm, not to Jamil and certainly not to himself. He's become prickly and defensive himself after all of his experiences--but that just adds to the complexity of his character when we synthesize what we know of him from TWST multimedia.

I really wish a lot of what was in the light novel post-Leona OB was also in the game. It would have helped to flesh out Leona's motivations and fears, which book 2 was sorely needing. As he is presented now, he appears shallow and selfish in his goals, and we don't fully understand the emotions spurring him on, a lot of which is genuine self-loathing and the sinking despair that comes with thinking you're not enough and you'll never be enough. That would have been so much more relatable than the in-game Leona having himself a pity party with a great amount of emphasis on the throne--a throne which, in actuality, just symbolizes a desire for recognition, love, and acceptance. It was never about explicitly being king. It was about being seen as his own person and appreciated for it instead of being admonished and compared to his exalted older brother.