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Lara Brennan is accused of murdering her boss after an altercation at work. Her college professor husband John Brennan becomes obsessed with the idea of breaking her out of jail.

John consults Damon Pennington, a hardened criminal who has successfully escaped from prison seven times, after reading Damon's book on the subject. Damon advises John to study the prison, saying "any prison has a key". Damon also warns him that the initial escape from the prison will be easy, compared to avoiding capture after the escape. To that end, John must obtain false passports, new social security numbers, and a "truckload of cash" to have a chance of building a life elsewhere. Damon also suggests going to an unstable foreign country that is politically hostile to the United States, so that there would be no extradition or cooperation with United States authorities. John learns the city's plan for capturing escaped prisoners—15 minutes after the escape, the police are to block the nearby roads, and that within 35 minutes, the block will extend to train stations and interstate toll stations, and that their descriptions will be at every airport and train station, though it may take longer for digital photos to be sent. John plans the escape meticulously and obtains the passports and social security numbers after some painful efforts.

Throughout the movie, John is shown assembling maps, photographs, notes, and other papers on a wall of his house. He tears them down and stuffs it into several garbage bags before leaving to rescue Lara, leaving one bag in the trash can outside his own house, and the rest in a dumpster some blocks away. As it turns out he did this selectively to misguide the detectives, to focus them on flights from Canada to Haiti, giving his family time to board a flight from Toronto to Caracas, Venezuela.