In the Chicago suburb of Hinsdale, Illinois, naïve, sheltered eleven-year-old Obadiah “Obie” Dawkins is devastated when his father has a heart attack and dies. After the funeral, Obie wears his father’s Rolex steel diver’s watch proudly, but is still hurting deeply. Obie gets upset after seeing a father kiss his son goodbye while dropping him off at school, something he did every day with his dad. He runs away from home, riding his bicycle to the south side of Chicago, but gets lost. When some teens offer to help, they lure him into an alley and steal the Rolex watch and his bicycle. An eleven-year-old street hustler named Jeremy “Scam” Henderson takes him to a bar to see a con man named Johnnie Red, who may have the watch. Johnnie denies having it, but they break into his apartment looking for it nonetheless. Johnnie catches them and admits that Obie’s muggers did give him the watch, but because it was not gold, he gave it to a pawn shop owner named Keegan. At the pawn shop, Obie finds the watch, but Keegan wants $180 for it. They say they’ll be back for it, then go to the run-down Paradise Hotel, where Scam has been living in the basement for the past two weeks after convincing the manager, Miss Hanks, that his father will be joining him soon. The two watch television and Scam confesses to Obie that his father is dead. The next morning, two hired killers, Doc and Dickie, park a dark gray Mercedes-Benz, with a dead body in the trunk, on the street and go into the hotel, just as Obie and Scam are leaving. Scam hot wires the car’s ignition and drives off with Obie, taking him to a bank where Obie withdraws money from his savings account. They return to the pawn shop where Keegan says the watch is $192.76 with tax. However, seeing the wad of cash that Obie has, Keegan takes the money without giving him the watch. Obie runs out crying, but Scam takes him back to the hotel where he gets two pistols. As they are leaving, they learn that Doc and Dickie are offering $1,000 reward for the Mercedes, so they hide the car in a back alley garage. They return to the pawn shop with the guns and demand the watch. Believing them to be toy guns, Keegan comes at them with a bat. Obie fires the pistol at the ceiling and they lock Keegan in the store money cage, then leave with the watch. However, Keegan sets off the burglar alarm, which brings police who arrest Scam and lock him in the backseat of their police car. Obie pretends to be unconscious, but as the policeman leans over him, the boy kicks the cop in the crotch, then gets in the driver’s seat and races off, even though he does not know how to drive. Other police cars give chase, but Obie eludes them. He drives into a trash dump and the two boys escape before police arrive. At a diner, Scam admits his father is still alive, but his mother died three months ago. His parents divorced when he was seven years old and his father went south looking for work. Scam has been on his own since his mother’s death and has no idea where his father is. Obie gets on a bus and returns home, much to his mother, Maggie’s, relief. When police question Obie, he says he was lost and is not sure where he was, that he must have “caught amnesia.” Obie returns to school, but misses Scam. He steals his mother’s Jeep Wagoneer and drives to the Paradise Hotel where he learns social workers took Scam to live at the Maple Street home. Police find Maggie Dawkins’s stolen car and have it towed away, so Obie goes to the garage to retrieve the Mercedes. Obie goes to the bar asking Johnnie Red to get Scam out of the home by pretending to be his father, Duane Henderson. Johnnie refuses, but when Obie pleads that Scam is the best friend he ever had, he consents. Once Scam is released, he and Obie go to the Internal Revenue Service office to see Obie’s Uncle Harry. With information from Scam’s father’s old driver’s license, they learn that Duane Henderson is working in Jefferson, Louisiana. The two boys start driving the Mercedes south to Louisiana, while Uncle Harry tells Obie’s mother what the boys are doing. Meanwhile, Doc and Dickie learn the boys have the car and pose as policemen questioning Maggie, who says the boys are headed to Louisiana. In Missouri, Obie and Scam pick up a hitchhiking Bible salesman who steals the Mercedes when they stop for food. Doc and Dickie see the Mercedes driving by, and give chase, but police stop the Mercedes for speeding and arrest the Bible salesman. Meanwhile, Obie and Scam get on a bus, but get off when they see the stopped Mercedes and steal it back. Doc and Dickie again give chase, repeatedly ramming their Lincoln Continental into the Mercedes, but crash into a ditch. Realizing the Mercedes is “hot,” Obie and Scam trade it for an old Cadillac convertible and go to the address in Jefferson looking for Scam’s father, but he is not there. However, police arrive with Obie’s mother, so the boys run out of the house and go to a bar looking for Scam’s father. A waitress says he works at a soap factory in nearby Madison, Louisiana. When they return to the convertible, Doc and Dickie grab them and take them back to the used car dealer, where Doc tries to take the Mercedes back at gunpoint. The boys escape from Dickie and run across the highway, causing a big rig truck to swerve into the car lot, where it explodes and kills Doc. Police find the dead body in the Mercedes trunk and arrest Dickie, who tries to pin the killing entirely on Doc and also mentions that the boys stole the car. When the boys do not have the $5 for ferry passage, Obie offers his watch as payment, but the ferryman lets them ride for free. Obie and Scam go to the soap factory and when workers leave at the shift change, Duane Henderson immediately recognizes his son. They have a tearful reunion. Soon after, Maggie Dawkins arrives and is reunited with Obie as well.