The storytelling frequently jumps between interviews with the real people portrayed in the film and the actual events performed by actors.
In 2003 in Lexington, Kentucky, Spencer Reinhard is an art student who feels his life has no meaning and that he needs something exciting, even if tragic, in his life to inspire greater artistry. Warren Lipka is a rebellious student on an athletic scholarship, though he does not care much for sports and is pursuing the education only to please his family.
After Spencer is given a tour of Transylvania University library’s rare book collection, the two plan to steal a first edition of John James Audubon’s The Birds of America and other rare books. Warren travels to Amsterdam to meet black market buyers who express interest. Upon returning to the U.S., he informs Spencer that they could make millions of dollars, much to their excitement.
Realizing that pulling off the heist will require more people, they enlist the help of childhood friends Eric Borsuk, who helps provide the logistics, and Chas Allen, who will be the getaway driver. They prepare for the job, learning that the only person guarding the books is the special collections librarian, Betty Jean Gooch.
On the day of the robbery, they disguise themselves as elderly businessmen and enter the library. After noticing that there are too many people in the special collections library for the job to succeed, they abort the heist and retreat. Three of the conspirators want to give up, but Warren calls the library asking for a private appointment the next day.
They drop the elaborate disguises. While Spencer acts as a lookout, Warren and Eric enter the library dressed as businessmen. Warren clumsily tases the librarian and makes Eric help tie her up and gag her. They take the rare books and blunder to an exit. In a panic, they drop and have to leave the biggest prizes, two enormous Audubon books comprising “The Birds of America”. All four manage to escape with two of the rarer books.
They take the books to Christie’s auction house in New York to get the authentication of value that Warren had said the Dutch buyers required. Spencer is told he has to return the next day and leaves his cell phone number with an assistant. In the van outside, Chas berates everyone for their stupidity, and they return to Lexington with the books. Shortly after, Spencer realizes that the police will be able to trace them from emails they used in setting up the heist as well as his cell phone number.
The thieves show signs of great stress as they try to lie low: Warren attempts to shoplift from a grocery store; Spencer gets into a car accident; and Eric starts a bar fight. Inevitably, the FBI raid their homes and arrest them. Movie titles show they each were sentenced to seven years incarceration.
After prison, the real-life robbers express their regret, noting how much pain they have put their families through. It is also revealed that Warren may have lied about going to Amsterdam, fabricating the story to get the others to agree to the heist. An epilogue describes their lives after prison. Eric lives in California as a writer, and Chas has become a fitness coach in Los Angeles. Warren has re-enrolled in college and studies filmmaking in Philadelphia. Spencer still lives in Lexington making a living as an artist, specializing in birds. Betty Jean Gooch, the librarian, still works at Transylvania University.