When asked if he has a hobby Leona says, “If I had to name something, it’d be chess.” Leona says that he enjoys studying chess boards and getting an idea of what is going on in his opponent’s head by examining their strategies.
Leona says that he used to play a lot of chess when he was a child, “and against big, important grown-ups, too,” who wouldn’t take him seriously, and they would “get all flustered by the end.”
It was possibly Kifaji who taught child-Leona how to play chess. Kifaji mentions Leona being a “cut little boy who threw tantrums when (he) beat (Leona) at chess,” and when Leona says a strategy he uses during the Cloudcalling tournament is a legitimate option in chess he adds, “Seem to remember some dodderin’ fool teachin’ me that in my youth.”
Kifaji responds, “Ah, was it a warm and kind chamberlain, perhaps? How lucky you were to have such a person in your life.”
Leona says that Kifaji “makes a decent chess opponent” and he seems to lack for any partners at NRC, to the point where he will play chess against himself.
Leona gifts Idia with a chess set for his birthday, but while they play a round together we are not told who, if either of them, won.
During the lantern event Leona provides his own personal chess set to help the group of Jack, Riddle, Kalim and Deuce escape the library.
Leona will mention chess in conversation, telling Floyd during Spectral Soiree that it “Doesn’t matter if you’re a bishop or a knight. If you don’t stick to your role on the chessboard, then you’re a liability,” and telling Malleus, “Every game piece has its use. I’m willing to put in just enough effort to figure out which one to play.”
Leona also refers to the other students as chess pieces during the Cloudcalling tournament, describing Lilia as their major piece, Vil as a minor piece and Kalim as a pawn.
After Kalim inadvertently purchases his victory in the tournament by buying his opponent a bus earlier on Leona observes, “Kalim seemed like a pawn to me, not even a minor piece. I can’t believe he got us a win. Though when pawns reach the other side of the chessboard, they can be promoted…”
Kifaji may have also taught Leona how to play pool. Leona explains,
“Ever since I was a kid. Had the game drilled into me so I wouldn’t embarrass myself in public. I mastered the ins and outs, which meant I stopped getting decent competition in the palace before I enrolled in school. Nowadays, the only guy who plays me is an old chamberlain who’s more chicken bones than man. Hardly satisfying.”
Leona gives an in-depth explanation of how to play pool at Playfulland, first beating him without Trey scoring a single point and then giving him an additional lesson, after which Trey manages to score 33 points to Leona’s 87.
Twisted Wonderland Reference Note 