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As the inmates of the Brockton Orphanage for Boys prepare for their August vacation, Leslie Henderson, a sensitive adolescent who has spent the year building a boat to sail to a desolated island nearby, invites little Allan to join him when the younger boy's vacation plans fall through. When Tom Bradley, one of the older boys, taunts Allan about his childish behavior, Les comes to his defense and a fight ensues. As a result, Mr. Gwinn, the supervisor of the orphanage, subtracts a week from Les's vacation and forbids Allan to accompany him. When Allan sobs in disappointment, Les tries to comfort the boy by promising him that tomorrow will be a better day. Afterward, Johnny Clancy, a scheming elder classman, chides Les for risking his own happiness to defend Allan. Clancy, who idolizes Max Cole, a former classmate who has become a successful businessman, points to Max's success and advises Les that he needs to "step over people" to achieve his own goals. One day, while roaming the swamps surrounding the orphanage, Les stops for a drink of water by the prison work gang overseen by Whittaker, a prison supervisor. There, Les tells Rudy Krist, a convict who earlier saved the boy's life by killing a deadly rattlesnake, about his boat. After Les leaves, Doosy, a weary, older convict, guesses that Rudy plans to steal the boat and sail to freedom. To achieve his escape, Rudy must be made a trustee, and soon, Plug, the brutal prison warden, promotes him to that position, threatening Rudy with death if he tries to escape. One day, Max arrives at the orphanage driving a shiny new Cadillac and accompanied by his attractive wife Maureen. When Clancy, who has been offered a job in Max's company, introduces him to Les, Max warns the idealistic Les to be wary because everyone is "out to get him." The next day, Max comes to see Les's boat, and when Max belittles both the boy and his craft, Maureen becomes upset at her husband's callousness. Later, when Les returns to the work gang to deliver some vegetables to Whittaker, Rudy pumps him for more information about his boat. Meanwhile, at the orphanage, Bradley begs Max for money to set up a small store in which to sell the driftwood figures he has made, and when Max humiliates Bradley, Maureen upbraids her husband. Afterward, Max, who has discovered that Clancy had been lying to him about his grades in order to wheedle a job in his company, rescinds his offer. Back at the prison camp, Rudy obtains Plug's permission to capture some rattlesnakes, but once he catches a reptile, Rudy turns it loose. When Whittaker raises his rifle to shoot it, Rudy smashes him in the head with a bucket and flees. To help his friend escape, Doosy acts as a decoy to fool the guards by running in the opposite direction. As the guards and their man-hunting dogs pursue the escaped convicts, Plug drives to the orphanage to warn Gwinn to keep the boys inside. Bradley, believing that he can prove his mettle to Max by capturing the convicts, takes off into the woods. Fearing for Bradley's safety, Max sets out with Les and Gwinn to find the boy. In the swamp, meanwhile, the police see Bradley's fleeting figure and set the dogs on him. After a dog kills Bradley, the police track Doosy to a shack owned by Philomena, a kindly recluse who has taken an interest in the orphans, and there they kill him. Hearing of Doosy's death, Les runs to Philomena's and tearfully watches as she buries his body. The next morning, as Les readies his boat for his voyage, Rudy jumps out of the woods, takes him prisoner and announces his plans to escape in the boat that night. Overwhelmed by the injustice and cruelty he has experienced, Les begins to rant about Max and "the other tough guys." After dark falls, Les and Rudy pull the boat over the marsh as Plug and his men lay in wait, determined to kill Rudy. As Rudy voices his obsession with "beating Plug," Plug spots the boat and fires, hitting Rudy, who falls overboard to his death. Upon reaching shore, Les decides to honor Rudy's last wish by concealing the fact that he was on the boat. Back at the orphanage, Plug accuses Les of being Rudy's accomplice. After Plug viciously slaps the boy, Max comes to Les's defense. Later, the sadistic warden is fired due to Max's influence. Les then tells Max that Rudy is dead. When Max offers Les a job, the boy refuses, claiming that he can make his own way following his moral compass.