Jackson is a clever middle schooler with a reputation for elaborate pranks and complex schemes. He comes from a family with a history of con artistry and strictly follows his grandfather's written Code of Conduct. While attempting to reform his mischievous ways to stay out of trouble, he finds himself drawn back into plotting when a political injustice threatens his friends and his school.

Gaby is a popular, athletic student who runs for class president with a platform focused on school improvements like an organic food bar. She is fiercely independent and competitive on the basketball court. Her relationship with Jackson is currently fractured due to a recent public incident, leaving her conflicted about his attempts to help her campaign.

Keith is a wealthy, entitled bully who uses his father's influence to manipulate the school system. He enters the Student Council race at the last minute purely to exact revenge on Jackson and Gaby for a past basketball defeat. He intends to use his political power to siphon funds from other student organizations into his Gamer Club.

Charlie is the editor of the school newspaper and serves as Jackson's most trusted confidant. He is highly protective of his twin sister Gaby and actively tries to shield her from Keith's underhanded tactics. He acts as the grounded voice of reason when Jackson pitches risky plans.

Dr. Kelsey is the corrupt principal of Maplewood Middle School who actively seeks reasons to expel Jackson. He prioritizes personal financial gain over administrative duties, readily accepting cash from wealthy parents to purchase office luxuries like an espresso machine.

Megan is a popular cheerleader who also serves as the brilliant president of the Tech Club. She balances her work in robotics and chemistry with her position on the cheer squad. She frequently faces assumptions from others who doubt her intelligence based on her appearance.

Hashemi is a gifted coder and inventor who constructs advanced devices, including a massive custom cell phone. He is a devoted science fiction fan who hides his memorabilia to avoid embarrassment. As the tech expert for Jackson's crew, he provides crucial electronic support for their operations.

Victor is a member of the Chess Team who joins Jackson's crew primarily to provide financial backing. He prefers reading classic literature to socializing and openly expresses annoyance at participating in the group's schemes, though his past bullying by Keith motivates his involvement.

Bradley is an art enthusiast and main office volunteer who idolizes Jackson's past exploits. He leverages his access to administrative areas to gather valuable intelligence for the crew. He is eager for inclusion and brings vital insider knowledge to the group's planning sessions.

Omar is a well-meaning but clumsy basketball player who harbors a strong crush on Gaby. He joins her campaign committee primarily to spend time with her, completely unaware that she only views him as a platonic friend.

Lynne serves as Gaby's original campaign manager. She is frequently distracted by social dynamics, school dances, and romantic gossip, often prioritizing these topics over serious political planning for the election.

Stewart is the starting captain of the football team who initially runs for class president to earn extra credit. He easily drops out of the race when Keith bribes him with an unreleased video game.

Wilton is the starting center for the football team and Keith's constant companion. He is running for class treasurer and frequently serves as a sounding board for Keith's egotistical plans, though he occasionally questions his friend's extreme tactics.

Samuel is Jackson's older brother who shares the family's legacy of complex pranks. He occasionally returns home to provide older-sibling guidance and logistical support for Jackson's endeavors.

Donald is Jackson's father and a special agent for the IRS. He balances his law enforcement career with a deep appreciation for his own father's history as a con man, passing down the family's strict Code of Conduct to his sons.

Miranda is a university professor who prefers her family to stay completely out of trouble. She actively discourages her husband from sharing stories about the family's criminal past with their sons.

Lincoln chairs the Student Honor Board and takes his administrative duties very seriously. He becomes highly flustered when managing official school procedures, especially when distracted by his crush on Megan.

Carmen leads the school's Environmental Action Team. She is highly passionate about green initiatives and readily employs aggressive tactics to support candidates who align with her ecological views.

Katie is the superintendent's daughter. Her brief, highly publicized interaction with Jackson caused massive social fallout, leading directly to the rift between Jackson and Gaby.

Mrs. Goldman is a long-serving administrative assistant at the middle school. She is easily distracted by radio contests and dreams of winning concert tickets.

Ms. Appleton is an administrative assistant who harbors clear biases against certain students. She frequently jumps to negative conclusions regarding Jackson's presence in the school office.

Roderick is Keith's wealthy and influential father. He believes he can purchase success for his son and routinely offers financial donations to the school to ensure Keith receives favorable treatment.

Naomi is Keith's cousin who runs for class secretary purely for financial compensation from her father. She shows little genuine interest in student government.