After deciding to drag Leona off of his dream throne in order to awaken him in Book 7 it is Ruggie who comes up with the idea of resurrecting Cheka, using his unique magic to control a 3D model crafted by STYX for the task.
(Azul: “Though I’m not sure how to feel about Ruggie performing the same motions at a distance.”)
Having met Cheka in person Ruggie is also nominated to the role of imitating Cheka’s voice for their mission, but he fails to deceive Leona.
Leona seizes Ruggie and reminds him that “treason against the crown is punishable by death,” invoking his unique magic in a recreation of the events of Book 2.
Ruggie is saved by a creation of Leona’s own mind, Kifaji.
The deeper level of Leona’s dream is a recreation of the interdorm spelldrive tournament, but an alternate timeline where Ruggie succeeded in trampling Malleus in his stampede.
Leona and the dream athletes begin plotting to use similar tactics to improve their midterm scores, and when Silver tries to assure Jack that Leona has merely been tainted by the darkness and would surely never attempt such a thing in reality Ruggie responds, “I dunno about that. Deep down, he’s definitely the type that would consider it. I’d know; I am, too.”
Twisted Wonderland Reference Note 