Leona brings over his own chessboard to help Jack and the lantern-event team when they become trapped in the school’s library and corrects their plan to go through every step of the story they are following to perfection: “As long as you attempt it in one way or another, that’s enough. Doesn’t matter if it’s serious or halfhearted…or if your pottery comes out ash.”
Riddle agrees, saying, “for once, his insights were quite welcome. It never occurred to me that a perfunctory approach was actually acceptable.”
During Playfulland Leona is the first person to come up with a successful strategy against the puppets: he sends the student group on ahead while staying behind to deal with a hoard of puppets on his own, locking them inside a building and thus thwarting them without suffering the consequences of doing damage to the park or breaking any rules.
Being conscious of when to conserve his energy and magic is a theme with Leona and a tactic he uses in Book 6 as he and Jamil fight their way through Tartarus, while Jamil worries about how to keep going without burning through his magic reserves.
Leona orders the same of his group during Spectral Soiree and mentions the importance of resting to Malleus, to Cater, and devises the most efficient way to help Jack’s group during the lantern event that requires the least amount of time and energy for the group to accomplish their goal.
Leona explains to Floyd that when his sleep quality drops it affects his thinking, which might also play a part in his prioritizing of conserving his energy.
During the NBC event Leona explains, “If you wanna make your preparations efficiently, you should focus on resting your mind and body for now.”
It is possibly due to this same line of thinking that Leona chooses to rest after outsmarting the Playfulland puppets, which leads to his downfall when he chooses to sit on the ground rather than in designated seating, thus breaking a rule of the park.
Vil laughs at the concept of Leona teaching rules to anyone, but it is not unusual for Leona to act according to the rules: just not in the way that others want him to.
When Jack transforms into a wolf in front of Leona for the first time Leona’s reaction is to call him out for rule-breaking, saying, “Transformation potions are forbidden.”
Leona uses such a loophole in Book 2 when he allows students of his dorm to physically and magically fight against the group of Cater, Ace, Deuce and Grim via a spelldrive match (“it doesn’t violate any school rules to cast spells during a game of Spelldrive”), but this tactic comes back to bite him him in the end when Trey, Jamil and the rest of the injured students ask that Savanaclaw not be disqualified from the spelldrive tournament specifically so that they can have their revenge, with Cater saying, “You’ve said it yourself, Leona-fighting doesn’t break school rules if it’s part of a Spelldrive match!”
Afterwards Ruggie says, “we took a beating from every other dorm on the way to the finals,” but it seems that they did reach the finals for the first time since Leona became housewarden (due to Savanaclaw being matched against Diasomnia in the first round of the tournament for two years in a row).
Twisted Wonderland Reference Note 