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Jack tells readers about all the violence he experienced in prison. Also, Jack tells us about how his dad knew who all the criminals were in his town, but he never predicted that Jack would be a criminal too.

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Jack worked as an electrician in Puerto Rico, but then decided he wanted to finish high school. As a result he moved back to Florida to live with the Bacon family. He was drinking too much and vomited all over their house. Then, the Bacon family kicked him out!

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Jack's high school used to be a prison and the principal invited prisoners to the school to warn the students about making bad choices. Also, he starts abusing his freedom by drinking and going to parties. Later, he visits the University of Florida but he decides it's not the right fit for him because he cannot have his car.

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Jack begins his road trip to visit the homes of famous writers so he can get inspired to write his own stories. His friend Tim Scanlon visits and they make a plan to sell some drugs so he can pay for college. Unfortunately the plan doesn't work and Jack loses $200.  He does not write anything significant, and he continues to drink and smoke.

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When Jack arrives to St. Croix he finds drugs everywhere and racial tensions are high. It's very dangerous. Since Jack and his father are building crates for people moving off the island, Rik visits their warehouse and asks for a false bottom box to ship drugs. Later, Jack decides to visit the Black Revolutionary Headquarters to interview the leaders, but he was cowardly and doesn't get to write his story. Lastly, Rik makes a proposal to sail a boat full of drugs to New York in exchange for 10,000 cash! Jack accepts.

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Jack and Hamilton practice sailing, but it does not go well because Jack does not have a lot of experience. To add, he and Hamilton do not get along well. Jack finds a green journal and decides to make it his own log of his adventures on the boat.

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Jack and Hamilton sail from St. Croix to New York and they have many obstacles. For example they ran out of fuel, didn't have a lot of fresh food, and they did never knew their exact location while on their trip. Additionally, Hamilton and Jack did not get along and had many issues with each other.

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Hamilton and Jack arrive in New York and suspicious events keep happening like they think they're being followed and 2 strangers were on their boat.

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Jack calls his father from Florida to discover that the authorities are looking for him.  He travels back to New York to meet his lawyer, Mr. Newman who believes that Jack doesn't have to worry too much about his punishment.  Unfortunately, the prosecution's lawyer, Mr. Tepper, has a lot of incriminating evidence.

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Jack waited at the Chelsea hotel before his sentencing day and he was hurting his face because he felt awful about his circumstances.  He tried to apply to some colleges, he went to the bars, he watched the news about the prison riots and he buried the extra drugs in Central Park.

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Jack has his court day and tries to show remorse, but the judge doesn't buy it. Jack is sentenced to 60 days - 6 years. His first night in jail is terrifying because he was exposed to a lot of violence and he even saw customer, Lucas in a terrible situation.

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The prison is filled with drugs, however Jack is not using them because he wants to get out sooner. His job as an x-ray tech is helping him stay safe and build strong relationships with the other prisoners. Jack has a meeting with his parole board and they tell him he has to wait at least 2 more years before he can see them again.