A young George Jung and his parents Fred and Ermine live in Weymouth, Massachusetts. When George is 10 years old, Fred files for bankruptcy, but tries to make George realize that money is not important.
As an adult, George moves to Los Angeles with his friend "Tuna"; they meet Barbara, an airline stewardess, who introduces them to Derek Foreal, a marijuana dealer. With Derek's help, George and Tuna make a lot of money. Kevin Dulli, a visiting college student from Boston, tells them of the demand for marijuana back home. They start selling marijuana there, buying marijuana directly from Mexico with the help of Santiago Sanchez, a Mexican drug lord. Two years later, George is caught in Chicago trying to import 660 pounds (300 kg) of marijuana and is sentenced to two years. After unsuccessfully trying to plead his innocence, George skips bail to take care of Barbara, who dies from cancer. Her death marks the disbanding of the group of friends.
While hiding from the authorities, George visits his parents. George's mother calls the police, who arrest him. He is sentenced to 26 months in a federal prison in Danbury, Connecticut. His cellmate Diego Delgado has contacts in the Medellin cartel and convinces George to help him go into the cocaine business. Upon his release from prison, George violates his parole conditions and heads down to Cartagena, Colombia to meet with Diego. They meet with cartel officer Cesar Rosa to negotiate the terms for smuggling 15 kilograms (33 lb) to establish "good faith".
As the smuggling operation grows, Diego is arrested, leaving George to find a way to sell 50 kg (110 lb). George reconnects with Derek in California, and the two sell all the cocaine. George then goes to Medellín, Colombia and meets Pablo Escobar, who agrees to go into business with them. With the help of Derek, the pair become Escobar's top U.S. importer. At Diego's wedding, George meets Cesar's fiancée Mirtha and later marries her. However, Diego resents George for keeping Derek's identity secret and pressures George to reveal his connection. George eventually discovers that Diego has betrayed him by cutting him out of the connection with Derek. Inspired by the birth of his daughter and a drug-related heart attack, George severs his relationship with the cartel.
All goes well with George's newfound civilian life for five years, until Mirtha organizes a 38th birthday party for him. Many of his former drug associates attend, including Derek, who reveals that Diego eventually cut him out as well. The FBI and DEA raid the party and arrest George. He becomes a fugitive, and his bank account—heretofore under Manuel Noriega's protection in Panama—is seized by Noriega. One night, he and Mirtha get into a fight while driving. They are pulled over by police and Mirtha tells them George is a fugitive and has stashed a kilogram of cocaine in his trunk. He is sent to jail for three years, Mirtha divorces him, and takes custody of their nine-year-old daughter, Kristina Sunshine Jung.
Upon his release, George struggles to maintain his relationship with his daughter. He promises Kristina a vacation in California and seeks one last deal to garner enough money for the trip. George completes a deal with former accomplices but learns too late that the deal had been set up by the FBI and DEA, with Dulli and Derek having leaked the nature and location of the action in exchange for pardons for their involvement in his prior action. George is sentenced to 60 years at Otisville Correctional Facility in upstate New York. He explains in the end that neither the sentence nor the betrayal bothered him, but that he can never forgive himself for having to break a promise to his daughter.
While in prison, George requests a furlough to see his dying father, Fred. His mother denies the request. George records a final message to Fred, recounting his memories of working with his father, his run-ins with the law, and finally, too late, his understanding of what Fred meant when he said that money is not "real". An old man in prison, George imagines that his daughter finally comes to visit him. She slowly fades away as a guard calls for George. The film concludes with notes indicating that Jung will not be eligible for parole until 2015, and that his daughter has yet to visit him.
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