Deuce is the only Heartslabyul student to ally against Riddle with Ace in Book 1, and joins Ace in challenging Riddle for the position of housewarden, though he at first intends to use physical assault rather than magical.
Post overblot Riddle begins to cry and when Ace declares he still won’t be forgiving him Deuce tells him to give Riddle a break.
Deuce will occasionally reference being afraid of Riddle, saying during Halloween that he isn’t scared of ghosts compared to having to deal with Riddle when he’s angry.
Deuce seems to enjoy it when Riddle compliments him, telling Sebek a story about a time he chased down a student trying to escape Riddle’s judgement: “get this—after Housewarden Riddle finished dressing down the rulebreaker, he complimented me!”
Deuce also seems pleased when Riddle compliments his Glorious Masquerade outfit (“hearing you say that makes me feel a lot more comfortable”), and after hearing of Deuce’s exploits from Rook Riddle praises him for his courage, offering to hold a tea party in his honor at Heartslabyul.
(Deuce: “I’m flattered… But if Ace finds out I got riled up and said all that stuff, he’ll make fun of me for days.”)
When Riddle refers to Deuce as “an exceptional card soldier” during the lantern event Deuce responds, “I’m honored by the compliment, Housewarden!”
Riddle says, “Deuce is a serious and exemplary student, but I do wish he’d be more prudent.”
After trying to surf for the first time Riddle says he wants to invite the rest of Heartslabyul to the beach sometime, as Cater and Deuce would especially enjoy it.
Twisted Wonderland Reference Note 