In this documentary, filmmaker Lucas Jansen explores the strange life of J.L. Rountree, who is best known as the oldest active bank thief. For most of his life, Rountree is an affluent white-collar man with a satisfying home life. However, in time he suffers both personal tragedies and financial ruin, after which he decides to turn to crime. Rountree executes his first heist at age 86 and his last at 92, only to end up in prison for the holdups he masterminded as a senior citizen.