Leona and Trey

Leona invites Trey to play pool with him at Playfulland, with Trey not scoring a single point during their first match. Leona offers to give him a handicap and teaches him about “safeties,” and while Trey does start scoring points in the second round he still loses 87 to 33.

Trey says, “I guess I’ll have to up my game, if I wanna be decent competition for you next time.” (Leona: “Next time? After you got dragged along for someone else’s entertainment and summarily stomped? You must be a glutton for punishment.”)

During the NBC event Trey says that Leona’s clothes suit him so well it was a little scary (Vil: “…your words, not mine”), and Leona sends Barrel to offer a dirty lollipop to Trey and Riddle (Trey: “Could you please not redirect unruly children at us?!”).

It is also during the NBC event that Trey finds himself in a group with the unhappy pair of Leona and Malleus, who decide to have him settle argument by decided which of them is correct. Trey asks them to not use him as an intermediary for their arguments, and after Leona walks away Trey takes Malleus’ side (Malleus: “I’m glad you appreciate my reasoning, Clover”).

When he is next alone with Leona, however, Trey adapts in order to please him, agreeing when Leona says that Malleus’ approach is crude.

Leona then reveals that Malleus has been listening, and is not pleased that Trey would try to “curry favor” with them both.

Leona tell Malleus, “That’s the kinda guy he is…the world’s got no shortage of people who lie through their teeth. They’re the worst kind of people. You gotta watch out for them (Malleus: “Indeed. So I have learned”).

Trey insists, “I just…thought it’d be nice if you two could get along a little better…” and Malleus and Leona assure him that the biggest unifier of all is a common enemy (Trey: “You…don’t mean me, right? Right…?”)

Malleus then excuses himself (I’ll go after Clover. I believe he and I have…. much to discuss”), leaving Leona alone. Leona responds, “Just tell Trey that once we get back, I wanna have a word with him too.”

In Book 7 Cater blames himself for not doing more to help Trey with Riddle (Leona: “Don’t flatter yourself”), and Leona wonders at the content of Trey’s dream: Even in his wish-fulfillment dream, someone else stepped in and solved his problems for him. It makes no sense to me.”

After taking out the Ace and Deuce of Trey’s dream Leona leaves dream-Cater and dream-Riddle to Trey himself, saying, “You owe me.” (Trey: “Haha. That’s a little ominous. But thanks all the same.”)

Leona is collared in Riddle’s dream and he immediately orders Trey to overwrite the magic, resulting in Trey getting collared himself.

Leona: “I had a feeling.”
Trey: “Did you just use me to test it out?!”
Leona: “You think I’d accept being the only guy wearing this dorky collar?”)

After Riddle is swallowed by the abyss of his dream Trey begins to panic, and Leona reassures him with, “(Riddle is) capable of handling whatever wild stuff may or may not get thrown his way,” calling Trey an over-protective parent. Cater responds, “Leona’s got your number, Trey,” and Trey says ,”As a Heartslabyul student, I’m proud to hear Leona give Riddle the credit he deserves.”