Seeking revenge for the death of his father, a teenager uses his father’s spy gear to blackmail the bully who destroyed his father’s career.
Josh Rumdowner is a reclusive teenager filled with resentment over being mocked and bullied by the Caledonia Sheriff, the man who engineered the discharge of Josh’s father from the police force of the small New Hampshire town. Josh’s father has to commute to Boston for a job he never talks about. Josh’s father is tragically murdered in a car parked on a narrow street in Beacon Hill.
After his father’s funeral, Josh is more withdrawn than ever. He quarrels with his mother over unpaid bills and her willingness to talk to the Sheriff. While Josh is collecting his father’s effects, he discovers a key which he eventually uses to open a locked door to a private room filled with spy gear used by his father in his job as a private investigator.
Josh recruits another marginalized classmate, Tally Hobart, to join him in snooping on the Sheriff by using the high tech video and audio devices in his father’s cache. The two peeping teens gather an impressive catalog of compromising evidence of wrong-doing by the Sheriff and a local Realtor King Pin. The boys design a string of blackmail drops using high tech tricks to avoid detection.
At first, their demands are modest, and the blackmailed big shots make the pay-offs in a series of scenes in which the two boys barely avoid detection. The boys raise their demands. Feeling the pressure, the Sheriff secretly suspects the Realtor and vice versa. The last people the Sheriff and the Realtor suspect are two low-profile teenagers.
Josh and Tally pile up increasing amounts of money in a joint bank account in a neighboring village. When a bank clerk named Norman Clark figures out what’s going on, he begins blackmailing Josh and Tally.
Norman demands $20,000 be left at the top of a ski lift. Josh and Tally make the same demand of the Sheriff, who surrounds the drop area with his hired hands on snowmobiles. Norman arrives to collect the ransom and the Sheriff’s henchmen close in. Josh and Tally use the chase as cover for their elaborate plan to steal away with the $20,000.
Wearing civilian clothes, the Sheriff entices Norman to jump into the Sheriff’s unmarked car to get away from the pursuing snowmobiles. The Sheriff parks his car at the top of a cliff overlooking a lake. When the Sheriff threatens Norman, the blackmailer doesn’t take time to figure out the double-blackmail, he just bolts out of the car, runs madly away, and accidentally falls over the cliff to his death.
In a subsequent complicated series of fake letters, Josh and Tally turn the Sheriff against the Realtor and their own indiscrete actions expose them as drug users and clients of escort services.
Josh and Tally have come so close to being caught so often that they swear off spying. Josh entrusts the spy gear to Tally who fences it in Boston. Josh and Tally split their ill-gotten gains and Josh pays off his mother’s bills and mortgage, refusing to tell her where the money came from.
Josh observes a local merchant making an illicit drug buy. He calls Tally and asks if he can rent back some of the spy gear from the fence so they can pull one more blackmail caper. Tally says, “Only if it’s worth the money.” Of course, it is.