Jack’s dream takes place in an alternate timeline directly before the interdorm spelldrive tournament of Book 2, where he is enjoying practicing the game alongside Leona and Ruggie as they compliment his skills.
After realizing that he is in a dream Jack begins to cry, calling both his upperclassmen out for their actions.
The dream-Ruggie encourages Jack to go back to reality after he gets to experience the tournament of his dreams but Jack declares, “The ones I looked up to, the ones I wanted to go all out…that wasn’t you guys!”
Jack is reluctant to awaken Ruggie from a dream where his father has returned, he is beloved by the townsfolk and never goes hungry (“I know it’s the right thing to do. It’s just, it seems kinda…l dunno, sad”), but agrees after Azul reminds him how Ruggie’s only actual family is likely worrying about him in reality: “This…this isn’t what Ruggie would want.”
Idia encourages Jack to try to wake Ruggie up with “an unforgettable anecdote to give him a mental shake” but Jack responds, “Ruggie doesn’t like talkin’ about himself… it’s hard to think of any.”
(Silver also fails to come up with any anecdotes, saying that he and Ruggie are in different classes and different clubs.)
At the conclusion of Leona’s dream Jack begins to cry, saying that both Leona and Ruggie were awful in his dream: “I mean, you’re both still jerks, but l’d take the real you over those fakes any day.”
Twisted Wonderland Reference Note 