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* AmbiguouslyEvil: Well, not ''evil'', but Naomi Sinclair's one scene makes it hard to tell if she's really a toady for her cousin who will do whatever he says, or if both Keith and his enemies merely wrongly take it for granted that she'll support his sinister plans due to their family relationship.
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* AmbiguouslyEvil: Well, not ''evil'', but Naomi Sinclair's one scene makes it hard to tell if she's really a toady for her amoral cousin who will do whatever he says, or if both Keith and his enemies merely wrongly take it for granted that she'll support his sinister plans due to their family relationship.relationship and she has more integrity and independence than that.
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* AmbiguouslyEvil: Well, not ''evil'', but Naomi Sinclair's one scene makes it hard to tell if she's really a toady for her cousin who will do whatever he says, or if both Keith and his enemies merely take it for granted that she'll support his sinister plans due to their family relationship.
to:
* AmbiguouslyEvil: Well, not ''evil'', but Naomi Sinclair's one scene makes it hard to tell if she's really a toady for her cousin who will do whatever he says, or if both Keith and his enemies merely wrongly take it for granted that she'll support his sinister plans due to their family relationship.
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[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/17928557.jpg]]
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* CheekCopy: The copy room has been locked ever since Jackson’s brother used school equipment to make photocopies of his butt.
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* SympatheticInspectorAntagonist: In ''To Catch a Cheat'', Honor Board Serena Bianchi is obsessed with investigating Jackson and busting him for his HighSchoolHustler antics. She hopes that doing so will get her made head of the Honor Board, but also has a lot of genuine indignation about how Jackson keeps getting away with outrageous misbehavior. She is compared to Isabel Lahiri from ''[[Film/OceansEleven Ocean's Twelve]]'', [[spoiler:right down to being manipulated and ultimately befriended by the main characters.]]
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* SympatheticInspectorAntagonist: In ''To Catch a Cheat'', Honor Board member Serena Bianchi is obsessed with investigating Jackson and busting him for his HighSchoolHustler antics. She hopes that doing so will get her made head of the Honor Board, but also has a lot of genuine indignation about how Jackson keeps getting away with outrageous misbehavior. She is compared to Isabel Lahiri from ''[[Film/OceansEleven Ocean's Twelve]]'', [[spoiler:right down to being manipulated and ultimately befriended by the main characters.]]
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* TeenGenius: Despite being a gossipy cheerleader, Megan is a top student in chemistry, electronics, and computer programming.
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* TeenGenius: Despite being a gossipy cheerleader, Megan is a top student in chemistry, electronics, and computer programming.programming, and her rival Kayla Hall is just as intelligent.
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* StealthMentor: In ''To Catch a Cheat'', [[spoiler:Lincoln Miller spends a lot of the book acting as a sounding board and DaChief for Honor Board SympatheticInspectorAntagonist Serena Bianchi as she tries to catch Jackson. The ending reveals that Lincoln has been helping Jackson trick Serena into busting the villains while also seeking to give the rigid Serena an unorthodox learning experience meant to let Lincoln observe how determined Serena can be and help her become more comfortable with trusting well-meaning rulebreakers as she seeks to become chair of the Honor Board]].
* SympatheticInspectorAntagonist: In ''To Catch a Cheat'', Honor Board Serena Bianchi is obsessed with investigating Jackson and busting him for his HighSchoolHustler antics. She hopes that doing so will get her made head of the Honor Board, but also has a lot of genuine indignation about how Jackson keeps getting away with outrageous misbehavior. She is compared to Isabel Lahiri from ''[[Film/OceansEleven Ocean's Twelve]]'', [[spoiler:right down to being manipulated and ultimately befriended by the main characters.]]
* SympatheticInspectorAntagonist: In ''To Catch a Cheat'', Honor Board Serena Bianchi is obsessed with investigating Jackson and busting him for his HighSchoolHustler antics. She hopes that doing so will get her made head of the Honor Board, but also has a lot of genuine indignation about how Jackson keeps getting away with outrageous misbehavior. She is compared to Isabel Lahiri from ''[[Film/OceansEleven Ocean's Twelve]]'', [[spoiler:right down to being manipulated and ultimately befriended by the main characters.]]
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* AlwaysSomeoneBetter: In ''To Catch a Cheat'', Megan is repeatedly frustrated when opposing "tech guru" Kayla Hall pulls off complicated computer programming jobs in less time than it would have taken Megan to do the same work.
* PunchClockVillain: In ''To Catch a Cheat'', villainous hacker Kayla Hall is laidback whenever she's not helping the BigBad with his schemes in order to finance her computer upgrades and doesn't hate any of the heroes besides Megan (who once got her banned from a robotics tournament and then gloated about it). She is willing to talk shop and share cookies with her antagonists, tells them that she has a contract that forbids her from naming her employer, and then goes back to trying to set them up for her boss after that meeting.
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* SmallRoleBigImpact: Keith's cousin Naomi is never mentioned again after the fourth chapter (out of forty-four), but her unopposed run for student council threatens to give Keith and Wilton a tiebreaker vote if they win their own bids.
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* SmallRoleBigImpact: Keith's cousin Naomi is never mentioned again after the fourth chapter (out of forty-four), forty-four) of the first book, but her unopposed run for student council threatens to give Keith and Wilton a tiebreaker vote if they win their own bids.
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* RacialFaceBlindness: Mrs. Appleton, the senior administrative assistant, can't tell Hispanic or Asian students apart regardless of their country of ancestry [[RacistGrandma and makes little effort to try.]]
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* InformedFlaw: Jackson and his friends talk about Wilton as if he's a BarbaricBully and SycophanticServant to Keith, but most of Wilton's [=POV=] scenes have him seem like a MinionWithAnFInEvil who is slowly getting fed up with Keith'a jerkiness.
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* InformedFlaw: Jackson and his friends talk about Wilton as if he's a BarbaricBully and SycophanticServant to Keith, but most of Wilton's [=POV=] scenes have him seem like a MinionWithAnFInEvil who is slowly getting fed up with Keith'a Keith's jerkiness.
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* PomPomGirl: Megan is a cheerleader (although she quits the squad during the TimeSkip between books to pursue her other interests), an avid {{Trekkie}}, rarely has a mean word for anyone, runs the Tech Club, and is quick to volunteer for Jackson's {{Zany Scheme}}s.
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* PomPomGirl: Megan is a cheerleader (although she quits the squad during the TimeSkip between books to pursue her other interests), an avid {{Trekkie}}, rarely has a mean word for anyone, to say about anyone remotely sympathetic, runs the Tech Club, and is quick to volunteer for Jackson's {{Zany Scheme}}s.
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* SoreLoser: Prior to the first book, Keith and Katie lost a basketball game to Jackson and Gaby by fifteen points. A sore Keith accused Katie of incompetence (she dumped him in response) and the referees of corruption.
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* SoreLoser: Prior to the first book, Keith and Katie lost a basketball game to Jackson and Gaby by fifteen points. A sore Keith accused Katie of incompetence (she dumped him in response) response), Jackson of cheating, and the referees of corruption.
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* PomPomGirl: Megan is a cheerleader (although she quits the squad during the TimeSkip between books to pursue her other interests), an avid {{Trekkie}}, rarely has a mean word for anyone, and is quick to volunteer for Jackson's {{Zany Scheme}}s.
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* PomPomGirl: Megan is a cheerleader (although she quits the squad during the TimeSkip between books to pursue her other interests), an avid {{Trekkie}}, rarely has a mean word for anyone, runs the Tech Club, and is quick to volunteer for Jackson's {{Zany Scheme}}s.
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* BigJerkOnCampus: Keith Sinclair is a wealthy, preppy athlete who has access to lots of unreleased video games, but he treats people badly. This actually makes him pretty ''un''popular though.
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* BigJerkOnCampus: Keith Sinclair is a wealthy, preppy athlete who has access to lots of unreleased video games, but he treats people badly. This actually makes him pretty ''un''popular (save with sycophants and impressionable younger kids) though.
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* HufflepuffHouse: There are eleven mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Debate Team, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, the football players, and the Art Geeks. The same can't be said for the Drama Club.
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* HufflepuffHouse: There are eleven mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Debate Team, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, the football players, and the Art Geeks.Geeks (or multiple organizations at a time). The same can't be said for the Drama Club.
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* SchoolClubsAreSeriousBusiness: Both the heroes and villains of the books care greatly about preserving the statuses of their own clubs, while Keith the bad guy is eager to force his rival clubs to disband. Tech Club president Megan Feldman dumps her boyfriend Stewart the moment she finds out that he took a bribe to help let Keith, a "sworn enemy of the Tech Club," to run for student council president when he would have been ineligible otherwise.
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* SchoolClubsAreSeriousBusiness: Both the heroes and villains of the books care greatly about preserving the statuses of their own clubs, while Keith the bad guy is eager to force his rival clubs to disband. Tech Club president Megan Feldman dumps her boyfriend Stewart the moment she finds out that he took a bribe to help let Keith, a "sworn enemy of the Tech Club," to run for student council president when he would have been ineligible otherwise.
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* SchoolClubsAreSeriousBusiness: Both the heroes and villains of the books care greatly about preserving the statuses of their own clubs, while Keith the bad guy is eager to force his rival clubs to disband. Tech Club president Megan Feldman dumps her boyfriend Stewart the moment she finds out that he took a bribe to help let Keith, a "sworn enemy of the Tech Club," to run for student council president when he would have been ineligible otherwise.
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* AscendedFanboy: Bradley starts out as an office messenger who's in awe of Jackson's legendary capers. He ends up as a trusted member of Jackson's CaperCrew.
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* FiveTokenBand: Of the six members of Jackson's team, Jackson is African-American, Victor is Chinese-American, Hashemi is Middle Eastern, Bradley and the AmbiguouslyJewish Megan are white, and Charlie is Hispanic.
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* FiveTokenBand: Of the six members of Jackson's team, Jackson is African-American, Victor is Chinese-American, Korean-American, Hashemi is Middle Eastern, Bradley and the AmbiguouslyJewish Megan are white, and Charlie is Hispanic.
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* LandslideElection: When Keith [[spoiler:tries to replace the ballots for Gaby with ones for him before being caught, he's discouraged by how many there are.]]
--> ''[H]e hadn't counted on so many students voting for [[spoiler:Gaby]]. (And by "so many," he meant "everyone.")''
--> ''[H]e hadn't counted on so many students voting for [[spoiler:Gaby]]. (And by "so many," he meant "everyone.")''
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* VictoriasSecretCompartment: This is implied when Megan has to hide a miniature microphone somewhere near her mouth and she has a strapless dress with no pockets. She takes the microphone and heads toward the restrooms, while Hashemi gets quite embarrassed.
* VillainWithGoodPublicity: Keith's dad is a respected industrialist who acts environmentally conscious. He only cut his carbon footprint to get tax cuts, bribes school officials to get whatever his family wants, and is called "merciless" by Dr. Kelsey.
* VillainWithGoodPublicity: Keith's dad is a respected industrialist who acts environmentally conscious. He only cut his carbon footprint to get tax cuts, bribes school officials to get whatever his family wants, and is called "merciless" by Dr. Kelsey.
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* AbsurdlyPowerfulStudentCouncil:
** The characters lampshade how the broad-minded school founders gave the student council unprecedented amounts of authority. The student council is made up of 30-40 kids, but whenever there's no quorum at a meeting (which happens a lot due to class schedules) the Executive Council can pass rules on the entire council's behalf. There are five kids on the Executive Council, but since they only need a majority vote, in theory ''three'' kids can make irreversible decisions regarding the lunch menu, disposal of paper waste, and the budgets for student organizations. This gives Jackson and Hashemi OhCrap reactions when their enemy Keith, his cousin, and his best friend all run for Executive Council positions.
** When presented with evidence of any wrongdoing, Honor Board members have the authority to nullify election results, order investigations, and ban malefactors from any future elections without needing a hearing or the principal's permission.
* AmbiguouslyEvil: Well, not ''evil'', but Naomi Sinclair's one scene makes it hard to tell if she's really a toady for her cousin who will do whatever he says, or if both Keith and his enemies merely take it for granted that she'll support his sinister plans due to their family relationship.
** The characters lampshade how the broad-minded school founders gave the student council unprecedented amounts of authority. The student council is made up of 30-40 kids, but whenever there's no quorum at a meeting (which happens a lot due to class schedules) the Executive Council can pass rules on the entire council's behalf. There are five kids on the Executive Council, but since they only need a majority vote, in theory ''three'' kids can make irreversible decisions regarding the lunch menu, disposal of paper waste, and the budgets for student organizations. This gives Jackson and Hashemi OhCrap reactions when their enemy Keith, his cousin, and his best friend all run for Executive Council positions.
** When presented with evidence of any wrongdoing, Honor Board members have the authority to nullify election results, order investigations, and ban malefactors from any future elections without needing a hearing or the principal's permission.
* AmbiguouslyEvil: Well, not ''evil'', but Naomi Sinclair's one scene makes it hard to tell if she's really a toady for her cousin who will do whatever he says, or if both Keith and his enemies merely take it for granted that she'll support his sinister plans due to their family relationship.
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* BathroomStallGraffiti: It's once noted that "[c]ontrary to the words scrawled across the walls of the boys' bathroom, Dr. Kelsey was indeed a smart man."
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* TheCaper: HighSchoolHustler Jackson and his allies set out to bolster Gaby's student council campaign while undermining Keith's after determining that Keith will use his AbsurdlyPowerfulStudentCouncil authority to cut the budgets for all of their clubs if he wins. This ultimately leads to a plan to rig the voting machines. [[[spoiler:Only that's just a bluff, and the real plan is to make Keith paranoid enough to tamper with the ballots himself and get caught in the process.]]
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* HeelFaceTurn: Wilton starts out as Keith's crony in bullying people and trying to steal the student council election. However, he gradually gets fed up with how paranoid and demanding Keith is and tells him to do his own dirty work.
--> '''Keith:''' You're supposed to be my right-hand man.
--> '''Wilton:''' No, I'm supposed to be your treasurer, but maybe I'll be Gaby's.
--> '''Keith:''' You're supposed to be my right-hand man.
--> '''Wilton:''' No, I'm supposed to be your treasurer, but maybe I'll be Gaby's.
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* HufflepuffHouse: There are eleven mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, the football players, and the Art Geeks. The same can't be said for the Drama Club.
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* HufflepuffHouse: There are eleven mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Debate Team, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, the football players, and the Art Geeks. The same can't be said for the Drama Club.
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* HufflepuffHouse: There are ten mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, and the Art Geeks. The same can't be said for the Drama Club.
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* HufflepuffHouse: There are ten eleven mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, the football players, and the Art Geeks. The same can't be said for the Drama Club.
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* WhatHappenedToTheMouse: Keith's ex-girlfriend Katie and Jackson are caught breaking into Dr. Kelsey's office in the prequel short story and they kiss to {{Troll}} Keith, who informed on them (which makes Gaby mad at Jackson). Afterward, Katie is frequently mentioned but never seen, and it's unclear what, if any, punishment she faced or if she has any further interactions with the main characters.
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* WhatHappenedToTheMouse: Keith's ex-girlfriend Katie and Jackson are caught breaking into Dr. Kelsey's office in the prequel short story and they kiss to {{Troll}} taunt Keith, who informed on them (which makes Gaby mad at Jackson). Afterward, Katie is frequently mentioned but never seen, and it's unclear what, if any, punishment she faced or if she has any further interactions with the main characters.
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* PomPomGirl: Megan is a cheerleader (although she quits the squad during the TimeSkip between books to pursue her other interests), an avid {{Trekkie}}, rarely has a mean word for anyone, and is quick to volunteer for Jackson's {{Zany Scheme}}s.
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BigJerkOnCampus Keith Sinclar sets out to rig a student council election and abuse his power once he wins. HighSchoolHustler Jackson Greene and his friends set out to sabotage Keith and ensure that his opponent Gaby (Jackson's crush, and his best friend's sister) wins by hook or by crook. The book has a sequel, ''To Catch a Cheat,'' where the heroes are blackmailed into helping some students cheat on a test, and plot to turn the tables. The books are written by Creator/VarianJohnson.
!!Tropes:
* AsianAndNerdy:
** Victor Cho is a self-proclaimed "intellectual nerd" who runs the chess club.
** Hashemi Larijani is a {{Trekkie}} and GadgeteerGenius.
* BestFriendsInLaw: Charlie and Jackson have been best friends and partners in crime since before Charlie's sister Gaby and Jackson developed feelings for each other.
* BigJerkOnCampus: Keith Sinclair is a wealthy, preppy athlete who has access to lots of unreleased video games, but he treats people badly. This actually makes him pretty ''un''popular though.
* TheChessmaster: For most of the book [[spoiler:it seems that Jackson is plotting to rig the voting machines. Actually, he's running a LongGame to manipulate Keith into getting caught trying to counter Jackson's supposed tampering.]]
* DeanBitterman: Dr. Kelsey takes a bribe to rig a student council election for a booster's son and relishes trying to crush free-spirited students who irk him.
* EatTheEvidence: In ''To Catch a Cheat,'' two kids who write test answers on their hands in invisible ink unsuccessfully try to lick it off their hands to destroy the evidence when [[spoiler:Jackson installs infrared bulbs which let the teacher see the invisible ink.]]
* FaceHeelTurn: [[spoiler:Victor is introduced as a bullying victim and useful CaperCrew recruit, but his selfishness makes him sell out the others. This makes him a minor pariah, and when he realizes that Jackson played him from the start, he resentfully becomes the BigBad of the sequel.]]
* FiveTokenBand: Of the six members of Jackson's team, Jackson is African-American, Victor is Chinese-American, Hashemi is Middle Eastern, Bradley and the AmbiguouslyJewish Megan are white, and Charlie is Hispanic.
* GirlyGirlWithATomboyStreak: Lynne and the other girls basketball team players are skilled athletes, but (save for Gaby) they spend most of their spare time buying clothes, talking about boys, and (in Katie's case) dancing.
* GossipyHens: Megan has a bad habit of blabbing juicy secrets to the Drama Club and her fellow cheerleaders, which is why Jackson shuts her out his HighSchoolHustler plots. Jackson lets her back into his circle of friends after she proves during a SecretTestOfCharacter that she's changed (he feeds her a false rumor about an AlphaBitch, and she doesn't tell anyone else).
* HighSchoolHustler: Jackson is never out for personal profit, but is a [[Film/Oceans11 Danny Ocean]]-esque figure who loves performing "heists" and pranks to help his friends and frustrate his enemies. It runs in his family.
* HufflepuffHouse: There are ten mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, and the Art Geeks. The same can't be said for the Drama Club.
* InformedFlaw: Jackson and his friends talk about Wilton as if he's a BarbaricBully and SycophanticServant to Keith, but most of Wilton's [=POV=] scenes have him seem like a MinionWithAnFInEvil who is slowly getting fed up with Keith'a jerkiness.
* PunctuatedForEmphasis: When Megan hears that Keith is brewing trouble for her beloved Tech Club, she says "Tell. Me. Everything."
* RealMenWearPink: In addition to being an athlete and HighSchoolHustler, Jackson is the head of the school's botany club.
* RuleNumberOne: Jackson has a set of rules for his HighSchoolHustler antics. Rule #1 is "No matter how simple a job looks, always plan before you act. A poorly constructed plan usually yields undersirable results." It's a rule Jackson is good at sticking to.
* SmallRoleBigImpact: Keith's cousin Naomi is never mentioned again after the fourth chapter (out of forty-four), but her unopposed run for student council threatens to give Keith and Wilton a tiebreaker vote if they win their own bids.
* SoapboxSadie: Carmen Cleaver runs a club dedicated to recycling, vegetarianism, and low carbon footprints. After Keith mocks her beliefs and deliberately throws a recyclable soda can in the trash to taunt her, she joins Gaby's campaign once it becomes clear they have some common beliefs. She also renames her club "Students against Keith Sinclair."
* SoreLoser: Prior to the first book, Keith and Katie lost a basketball game to Jackson and Gaby by fifteen points. A sore Keith accused Katie of incompetence (she dumped him in response) and the referees of corruption.
* TeenGenius: Despite being a gossipy cheerleader, Megan is a top student in chemistry, electronics, and computer programming.
--> '''Hashemi:''' She's like the UsefulNotes/ThomasEdison of middle school. Except, you know, pretty. And not dead.
* TookALevelInBadass: UnwittingPawn Lincoln becomes a BadassBureaucrat in the climax, and then a [[spoiler:StealthMentor]] in the sequel.
* UnspokenPlanGuarantee: Zigzagged. Jackson and Charlie openly talk about their plans (which go off flawlessly) well before the final act. However, they use code phrases that readers may or may not be able to decipher (e.g. "Anakin Skywalker" means [[spoiler:they are anticipating someone will betray them and have planned around that]]).
* WhatHappenedToTheMouse: Keith's ex-girlfriend Katie and Jackson are caught breaking into Dr. Kelsey's office in the prequel short story and they kiss to {{Troll}} Keith, who informed on them (which makes Gaby mad at Jackson). Afterward, Katie is frequently mentioned but never seen, and it's unclear what, if any, punishment she faced or if she has any further interactions with the main characters.
!!Tropes:
* AsianAndNerdy:
** Victor Cho is a self-proclaimed "intellectual nerd" who runs the chess club.
** Hashemi Larijani is a {{Trekkie}} and GadgeteerGenius.
* BestFriendsInLaw: Charlie and Jackson have been best friends and partners in crime since before Charlie's sister Gaby and Jackson developed feelings for each other.
* BigJerkOnCampus: Keith Sinclair is a wealthy, preppy athlete who has access to lots of unreleased video games, but he treats people badly. This actually makes him pretty ''un''popular though.
* TheChessmaster: For most of the book [[spoiler:it seems that Jackson is plotting to rig the voting machines. Actually, he's running a LongGame to manipulate Keith into getting caught trying to counter Jackson's supposed tampering.]]
* DeanBitterman: Dr. Kelsey takes a bribe to rig a student council election for a booster's son and relishes trying to crush free-spirited students who irk him.
* EatTheEvidence: In ''To Catch a Cheat,'' two kids who write test answers on their hands in invisible ink unsuccessfully try to lick it off their hands to destroy the evidence when [[spoiler:Jackson installs infrared bulbs which let the teacher see the invisible ink.]]
* FaceHeelTurn: [[spoiler:Victor is introduced as a bullying victim and useful CaperCrew recruit, but his selfishness makes him sell out the others. This makes him a minor pariah, and when he realizes that Jackson played him from the start, he resentfully becomes the BigBad of the sequel.]]
* FiveTokenBand: Of the six members of Jackson's team, Jackson is African-American, Victor is Chinese-American, Hashemi is Middle Eastern, Bradley and the AmbiguouslyJewish Megan are white, and Charlie is Hispanic.
* GirlyGirlWithATomboyStreak: Lynne and the other girls basketball team players are skilled athletes, but (save for Gaby) they spend most of their spare time buying clothes, talking about boys, and (in Katie's case) dancing.
* GossipyHens: Megan has a bad habit of blabbing juicy secrets to the Drama Club and her fellow cheerleaders, which is why Jackson shuts her out his HighSchoolHustler plots. Jackson lets her back into his circle of friends after she proves during a SecretTestOfCharacter that she's changed (he feeds her a false rumor about an AlphaBitch, and she doesn't tell anyone else).
* HighSchoolHustler: Jackson is never out for personal profit, but is a [[Film/Oceans11 Danny Ocean]]-esque figure who loves performing "heists" and pranks to help his friends and frustrate his enemies. It runs in his family.
* HufflepuffHouse: There are ten mentioned student organizations and teams. Important characters belong to the Tech Club, the Botany Club, the Gamer Club, the Environmental Action Team/Students Against Keith Sinclair, the Chess Team, [[SchoolNewspaperNewsHound the Maplewood Herald]], the Fighting Dolphins Basketball team, the cheer squad, and the Art Geeks. The same can't be said for the Drama Club.
* InformedFlaw: Jackson and his friends talk about Wilton as if he's a BarbaricBully and SycophanticServant to Keith, but most of Wilton's [=POV=] scenes have him seem like a MinionWithAnFInEvil who is slowly getting fed up with Keith'a jerkiness.
* PunctuatedForEmphasis: When Megan hears that Keith is brewing trouble for her beloved Tech Club, she says "Tell. Me. Everything."
* RealMenWearPink: In addition to being an athlete and HighSchoolHustler, Jackson is the head of the school's botany club.
* RuleNumberOne: Jackson has a set of rules for his HighSchoolHustler antics. Rule #1 is "No matter how simple a job looks, always plan before you act. A poorly constructed plan usually yields undersirable results." It's a rule Jackson is good at sticking to.
* SmallRoleBigImpact: Keith's cousin Naomi is never mentioned again after the fourth chapter (out of forty-four), but her unopposed run for student council threatens to give Keith and Wilton a tiebreaker vote if they win their own bids.
* SoapboxSadie: Carmen Cleaver runs a club dedicated to recycling, vegetarianism, and low carbon footprints. After Keith mocks her beliefs and deliberately throws a recyclable soda can in the trash to taunt her, she joins Gaby's campaign once it becomes clear they have some common beliefs. She also renames her club "Students against Keith Sinclair."
* SoreLoser: Prior to the first book, Keith and Katie lost a basketball game to Jackson and Gaby by fifteen points. A sore Keith accused Katie of incompetence (she dumped him in response) and the referees of corruption.
* TeenGenius: Despite being a gossipy cheerleader, Megan is a top student in chemistry, electronics, and computer programming.
--> '''Hashemi:''' She's like the UsefulNotes/ThomasEdison of middle school. Except, you know, pretty. And not dead.
* TookALevelInBadass: UnwittingPawn Lincoln becomes a BadassBureaucrat in the climax, and then a [[spoiler:StealthMentor]] in the sequel.
* UnspokenPlanGuarantee: Zigzagged. Jackson and Charlie openly talk about their plans (which go off flawlessly) well before the final act. However, they use code phrases that readers may or may not be able to decipher (e.g. "Anakin Skywalker" means [[spoiler:they are anticipating someone will betray them and have planned around that]]).
* WhatHappenedToTheMouse: Keith's ex-girlfriend Katie and Jackson are caught breaking into Dr. Kelsey's office in the prequel short story and they kiss to {{Troll}} Keith, who informed on them (which makes Gaby mad at Jackson). Afterward, Katie is frequently mentioned but never seen, and it's unclear what, if any, punishment she faced or if she has any further interactions with the main characters.
