Jack Sheppard is a historical figure born in 1702 in London, England. Sheppard was apprenticed to a carpenter named Kneebone and began his crime spree in 1723. Jack chose a life of crime over finishing his apprenticeship and becoming a professional carpenter. Sheppard escaped from prison four times over the course of two years between 1723 and 1724, making him a local legend among the working class. Sheppard was a short and wiry man, much like Jack in Confessions; his stature was often credited for his ability to make impossible escapes. The historical Sheppard had a minor stutter like his fictional counterpart.

Sheppard chose to remain a freewheeling thief rather than work for Thief-Taker General Jonathan Wild. Sheppard was arrested for a fifth and final time in late 1724. He was executed on November 16, 1724, at the age of 22. An autobiography of Sheppard was sold at his execution by Applebee’s Original Weekly Journal, the same publication that appears in Confessions; Sheppard endorsed this autobiography before being hanged. This autobiography was likely ghostwritten by the famous author Daniel Defoe, who was a journalist at the time and reported on famous criminals like Jack Sheppard and Moll King.