The film, set in modern-day NYC, follows the adventures of Jack Tyler, a 12-year-old boy, who has just lost his father, a venerated police officer, who was killed in the line of duty. The loss of his father causes Jack to act out in school in epic antics that get plenty of kudos from his peers, but the boot from not one, but five junior high schools. His mother, Diane, is not only struggling with endless bills as a now single mother, but with how to keep her now unenrolled, mischievous son, Jack, busy during the day due to her rigorous work schedule. With some hesitation, she agrees to have Jack temporarily work alongside Daniel, Jack's former partner on the force. Daniel is eager to have Jack join, since he needs a trickster to help outwit the trickster criminals, who are committing multiple unsolvable crimes of late. With Jack's ingenuity, creativity and outside of the box thinking, he is able to solve crime after crime. However, just when he is feeling confident about his new, emerging skill-set, criminals, who he previously thought he outwitted, strike again and this time it gets personal. With encouragement from his crush and now 12-year-old girlfriend, Jack is able to not only solve the final crime, but to attain the ultimate jackpot!