The young Tobias Wolff—who, in his youth, went by Jack—and his mother Rosemary are driving across the country from Florida to Utah. Rosemary is fleeing an abusive relationship and she hopes that in Utah, she and her son will be able to strike it rich in the uranium boom. When they get to Utah, however, they find that the mines have all dried up. Even worse, Rosemary’s abusive lover, Roy, has tracked them across the country, and as he begins worming his way back into Rosemary and Jack’s lives, Jack struggles with feelings of insecurity, anger, and the desire to get into trouble—feelings that are intensified when Roy buys him a rifle and teaches him how to shoot. After a few months, Rosemary and Jack flee Utah one afternoon while Roy is off on a hunting trip, boarding a bus bound for Seattle.
In Seattle, Jack and Rosemary take up residence in a boarding house while they get settled. Jack makes two good friends at school, both named Terry—he calls them by their last names, Silver and Taylor. The boys spend their afternoons lusting after girls on The Mickey Mouse Club and getting into trouble, egging cars, stealing cigarettes, and breaking windows around town. After several months, Jack and Rosemary move into a real house with two women from the boarding house, Kathy and Marian. When Kathy and Marian each get engaged, they urge Rosemary to start dating, too—they don’t know what Jack knows, which is that she has a history of striking up with violent men.
Rosemary begins dating a man named Dwight—though Jack doesn’t like him and thinks he’s oafish and dumb, Rosemary insists he’s a nice man. Rosemary begins spending more and more time with Dwight, and soon brings Jack up to Chinook, the village where he lives with his three children from a previous marriage, to meet Dwight’s family for Thanksgiving. After Thanksgiving, Jack begins getting into more and more trouble at school. One afternoon, Rosemary tells Jack that Dwight has proposed to her; she is unsure of whether she should accept his offer, and wants for Jack to move up to Chinook for a while to see if it’s possible to blend their families before she makes any serious decisions. Jack doesn’t want to go along with this plan, but feels he has no choice.
As soon as Jack arrives in Chinook, he begins seeing another side of Dwight—a side that is sullen, cruel, and just plain strange. On the way up to Chinook, Dwight purposely hits a beaver in the road, then urges Jack to pick up its carcass and load it into the trunk, as it’s valuable. When Jack is afraid to touch the carcass, Dwight does it himself, berating Jack for being so spineless. That evening, Dwight stops off at a tavern, leaving Jack alone in the car for several hours. Dwight emerges from the tavern drunk, and as he drives Jack home along the curving mountain roads, he berates him for being lazy, stupid, and cruel. Things get worse from there—Dwight subjects Jack to miserable and menial tasks such as shucking spiny horse chestnuts. He forces Jack to take on a paper route, but collects every cent Jack earns, claiming to be putting it in a savings account for Jack to use in the future. He signs Jack up for Boy Scouts, which Jack actually enjoys, but does so only so that he can observe Jack at all times and make sure all of Jack’s time is occupied. In the spring, Rosemary decides that she wants to accept Dwight’s proposal—on a trip up to Chinook, she asks Jack in private if everything with Dwight has been going all right, and insists it’s not too late to back out. Jack, again, feels trapped and tells his mother that everything is fine.
Jack struggles to make friends, avoiding nice and respectable boys like the “sissy” Arthur Gayle in favor of hanging out with older, wild high schoolers. He tries and fails to grow close to his new step-siblings Skipper, Norma, and Pearl, who have each in their own way been touched themselves by Dwight’s controlling nature. Dwight begins abusing Rosemary verbally and emotionally in front of the children, and as his disregard for her intensifies, Jack reaches out to Rosemary’s brother, who lives in Paris, writing a letter begging him to help them flee to France. Jack’s uncle writes back and offers to adopt Jack as his own son, but Jack knows he cannot leave his mother behind. Even though Dwight wants Jack out of the house and urges him to accept the offer, Jack declines it. Norma moves to Seattle and gets engaged to a terrible man named Kenneth; when she brings him home to meet the family for Christmas, Dwight suggests Jack get all the chestnuts he shucked out of the attic so that they can roast them together, but when Jack gets up there he sees that both the neglected chestnuts and the untreated beaver carcass have molded over into pulps.
By the time Jack starts high school, he is constantly fantasizing about alternate lives for himself and coming up with plans to run away from Chinook. He never follows through with any of them, and Dwight’s abuses get worse. Jack begins struggling in school, and starts drinking and getting into more and more trouble with his older, unruly friends Chuck Bolger and Jerry Huff. Jack begins writing letters to his estranged brother, Geoffrey, who is a student at Princeton; one afternoon, after Dwight beats Jack, Jack calls his brother and tells him what’s really going on. Geoffrey promises Jack that they’ll find a way to get him out of Washington, and he suggests Jack apply to some prestigious boarding schools. Jack has done miserably in school for years, though, and when the time comes to apply to these schools, he realizes that the image of himself he has constructed in his head does not match up with who he actually is. With the help of his sometimes-friend Arthur, Jack steals stationery and transcript forms from the school office, and forges his grades and letters of recommendations. Jack and Arthur begin fighting more and more, and when a teacher, Mr. Mitchell, recruits them for a boxing match, they face off against one another; as Jack lands blows against his friend, he worries that he has become someone Dwight is proud of.
Jack is rejected from all of the schools he applied to except one—the Hill School in Pennsylvania. An alumnus of the school, Mr. Howard, contacts Jack to inform him that the school is “interested” in admitting him, but wants to hear more about him first—Mr. Howard takes Jack out for a milkshake and informally interviews him. He warns Jack that prep school is not for everybody, but Jack insists that he badly wants to go to Hill. After Jack severs the tip of one of his fingers in shop class one day, he is hospitalized for a week; when he returns home, he is desperate to numb the pain, and steals some of Dwight’s whisky. When Dwight confronts him about the theft the two exchange verbal barbs. Dwight pushes Jack, causing him to fall on his bad finger; Rosemary tells Jack that she is getting him out of the house right away and putting a stop to the abuse. Chuck Bolger’s family agrees to take Jack in, but when Jack goes to live with Chuck, he realizes that his friend is an alcoholic who is subject to fits of drunken rage and self-harm. The boys get into more and more trouble, and when they are caught stealing gasoline from some neighbors, Mr. Bolger kicks Jack out of the house. Rosemary begs Mr. Bolger to keep Jack on for just a while longer, as he has nowhere else to go, and Mr. Bolger reluctantly agrees.
Chuck gets into more trouble when a girl he’s accused of impregnating threatens to press rape charges if he doesn’t marry her. The crisis derails Chuck’s life and sends him into a tailspin, as he tells the sheriff several times over a number of weeks that he’d rather go to prison than marry someone he doesn’t care about. The atmosphere in the Bolger house becomes miserable, but Jack receives some good news—he has been admitted to Hill on a nearly-full scholarship. Jack tells his mother the good news, and they rejoice together, though there is a dark spot in their celebrations; Dwight has stolen and hidden all of Jack’s paper route money. Nevertheless, Jack and Rosemary—who has secured a job in Seattle and is living there full-time—look forward to their futures. Chuck gets off the hook when his friend Jerry Huff agrees to marry the pregnant girl, and for a little while everything seems right.
Chuck and Jack break into Dwight’s house in the middle of the night one night. Jack steals all of Dwight’s hunting rifles, and, the following day, when Chuck drives Jack into Seattle so that he can meet with Mr. Howard and get fitted for clothes for school, the boys pawn the guns. Though they get almost no money, Jack rejoices in the simple act of taking something from Dwight just as Dwight took from him. Jack spends the summer in California with his father and brother, but his father suffers a mental breakdown and is admitted to a sanitarium. Jack goes off to school in the fall, and Rosemary follows him east, taking a job in Washington D.C. Over the Christmas holidays, Dwight shows up at her new apartment and tries to strangle her, but she fights him off and has him arrested. Jack struggles in school, having been woefully unprepared for such rigorous academics. He slacks off and gets into trouble again and again until, in his senior year, he is expelled and decides to join the army. The book ends as the older Tobias reflects on his youth and the “assurance” he once felt that his dreams were his right—an assurance that all young people feel, and which burns brightly for a few years before it fades away forever.