Will Shea
Will is the protagonist of the story. He is a clever and witty filled high school boy who has found a way to get into the prestigious Connaughton Academy. Will is a con artist, full of deception and tricks up every sleeve. He fakes a story of his poor life as an orphan on the Marshall Islands as his missionary parents were killed in a plane crash. However, this is all a lie and has won him a spot in the wealthy high school. All Will wants is to get away from his drunken, abusive father and start a new life for himself.
Andrea Dufresne
Andrea is the antagonist of the story. She too is a con artist with an almost identical story to Will’s and has claimed Connaughton Academy as her own. There is only room for one con in this school, and Andrea is ready to take her rightful place. She challenges Will to a bet: the first person to get $50,000 out of Brandt Rush, the wealthiest and worst bully in school, gets to stay. The loser has to leave. Andrea cannot lose, and she’s ready to do anything in order to win this game. She takes an approach only she can accomplish: becoming Brandt’s girlfriend. It’s a wild ride, and Andrea is ready to fight.
Brandt Rush
Brandt is the biggest, worst, most obnoxious bully in the whole of Connaughton Academy. He is so purely evil, it seems even a little inhuman. Readers have expressed wishes to see at least a slight slip of character in Brandt, wishing to see some human feelings within him. However, Brandt does not comply. He is entirely cruel and a big pain. However, he becomes the center of attention and of the utmost value to Andrea and Will. Without him knowing, he is being subjected to carefully crafted traps and lies to squeeze $50,000 out of his pocket. For Brandt, that kind of money is no bigger than some pocket change; he is rich and spoiled, coming from an extremely wealthy family and background. He is the least desirable person, yet he becomes the most valuable player in this game for two.
Gatsby
Gatsby is a worker in the library and is a member of the Sigils organization, an exclusive club in the Academy’s reputation. She also happens to be Will’s love interest. Not much is to be said about Gatsby because her character isn’t developed too extensively in the storyline. But she does manage to complicate the story because she distracts Will from his mission and makes the stakes higher for him, making him that much more desperate to win.
