13-year-old Jay Martin, a student at Columbus Hall, a private middle school, is competing for a scholarship to the prestigious Donald Peterson Academy with rival classmate and bully Ronny Van Dusen, son of the headmaster, Ward Van Dusen. Jay plans to study art during his time at Peterson, but the thing is, the scholarship is the only one of its kind available, and if his presentation doesn't help him obtain it, he will instead have to go to the all-boys Starkwell Military Academy upstate with his older brother, Mike (where their late father had been a student and teacher).
When Jay arrives at school with his best friends, Tracy Richburg and Bill Lipka, and shows them the presentation, by chance, Ward confiscates it due to Jay having made a flipbook with art on the other side of the presentation's note cards that depicts Ward as a big bad wolf, which the headmaster takes offense to. Ward later leaves the note cards lying around his office and tells Ronny to use them as a reference to come up with a better presentation. Being lazy, Ronny instead copies the presentation word-for-word while alone in his father's office, uses it in the contest, and wins the scholarship, much to Jay and his friends' dismay. When Jay brings this up with Ward, the headmaster initially declares his intention to look into the matter, only for Jay to soon after overhear him in his office criticizing his son for his plagiarism and demanding that he get rid of the evidence in order to preserve the Van Dusen family name, let alone make it look like Jay is the cheater.
Later that afternoon, heeding advice from Tracy and Bill that he needs evidence to prove Ronny's cheating and Ward's attempted cover-up, Jay breaks into the pool house of the Van Dusens' mansion (which Ronny uses as his hangout and bedroom) while the family is at the awards ceremony in order to take back his presentation and use it as evidence. However, during the search, Ward's wife, Eliza's show dog, Camille, discovers Jay, and follows him home after he is nearly caught by their maid, Adele, whom Jay scared away using Ronny’s hockey mask before she could figure out who he was. Camille goes crazy and wrecks the Martin's home when she goes too long without her medication. After Jay spends hours trying to comfort the dog, Camille can withstand no more and explodes.
Mike comes home from Starkwell to check in on his brother while their mother is away taking care of her injured aunt, and finds the house a mess and Camille with a nervous breakdown. After Jay confesses the entire situation, and Camille runs away, the two try to buy time to get Camille back home. During this time, Ward disavows any knowledge of Ronny's theft and plagiarism to Mike during a phone call, prompting Mike afterwards to reveal to Jay he and Ward had a long history of animosity towards each other when he was a student at Columbus, and that Ward also has had a long history of nepotism since he became headmaster; a perfect example of this being when Ward cut Mike from the school's baseball team to make room for his nephew, who had never even played baseball in his life. Eventually, the two manage to lure Camille back out with a plan that also attracts every dog in the neighborhood, and take her back to their house to work out their next move.
Meanwhile, the Van Dusens discover that Camille is missing, and based on Adele's recount of the disguised Jay leaving the pool house, deduce that she has been kidnapped. Ward eventually panics when he is visited by his father-in-law, Ronny's maternal grandfather, Armand Columbus, whose family line had been the original founders of the school; after Armand's retirement as the school's headmaster, he entrusted Ward with the position, but has started having doubts about him as of late. Although Armand advises him to get his daughter's dog back, Ward is hesitant due to having hated Camille to begin with, especially when it came to his allergies toward her (he had flushed his allergy medicine after the family learned Camille was missing); using this to their advantage, the boys anonymously force Ward to agree to numerous ridiculous acts just to get Camille home and Armand off his back. Over time, Jay also bonds with Camille.
Reaching his limit, Ward finally calls the police to tap into the calls he usually received from the boys (who used a voice disguiser to hide their identities). Upon discovering the police's involvement, Jay and Mike then come up with a plan to frame Ronny for the whole thing; as Ronny is relaxing in the pool house while the police are waiting for the phone call in the main house with Ward, Eliza, Armand and the servants, Mike poses as a BMX magazine salesman and gives Ronny a survey to distract him while Jay sneaks Camille into the pool house, and then has the police trace the call from there, planting the voice changer there as well for further incrimination. The plan works, and when the Van Dusens, Armand, the servants and the police find Camille in the pool house, Ward assumes that Ronny did all this as revenge for his parents refusing to buy him a BMX bike, with intent of using the ransom money to purchase the bike himself. However, this causes Armand to remark that "the apple doesn't fall very far from the tree" in realization that Ward has passed his corrupt behavior onto his son.
In the end, it is assumed that following Jay and Mike's frame job on Ronny for Camille's "kidnapping", Armand opens up an investigation and eventually uncovers both Ronny's plagiarism and Ward's attempted cover-up of it. As a result, Armand comes out of retirement and retakes his old job as headmaster of the school, while demoting Ward to secretary. He then reopens the Peterson scholarship competition, where he strips the scholarship from Ronny and rightfully awards it to Jay, shipping Ronny off to Starkwell as punishment afterwards. While Jay is talking to Armand in his office over graduation ceremony plans, Eliza comes in and reveals that Camille is pregnant. While Eliza plans to keep most of Camille's puppies, with Ward having no choice but to move into the pool house due to his allergies while Ronny is away at school, seeing how much Camille likes Jay, she gives Jay one of them. While Ronny is doing marches and drills at Starkwell, he finds, to his surprise, his instructor is none other than Mike himself.
- Tahj Mowry as Jay Martin
- Craig Kirkwood as Mike Martin
- Shia LaBeouf as Ronny Van Dusen
- Steven Bendik as Bill Lipka
- Sara Paxton as Tracy Richburg
- Rachelle Carson as Eliza Van Dusen
- Ed Begley, Jr. as Ward Van Dusen
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