Daniel Defoe's fifth novel, Colonel Jack is the supposed autobiography of an English gentleman who begins life as a child of the London streets. He and his two brothers (both also named Jack) are brought up as pickpockets and highwaymen, but Colonel Jack seeks to improve himself. Kidnapped and taken to America, he becomes first a slave, then an overseer on plantations in Maryland and Virginia. Returning to England, he is drawn into the Jacobite rebellion and into a succession of marriages, all of which end badly for him. Escaping back to Virginia, Jack becomes a successful planter, ending his life as a gentleman despite his mistakes along the way.

Historical appendices relate to eighteenth-century Virginia and Maryland and contemporary crime, punishment, and imprisonment.