This paper tells the story of Pesach Rubenstein and how he cheated the hangman in 1876. Rubenstein was charged, tried, and convicted in Kings County, New York, for the 1875 murder of his 19 year-old cousin, Sarah Alexander. The Rubenstein case is noteworthy in that it received unprecedented media attention in the 1870s, involved the use of rudimentary forensic evidence at the trial, and divided the community on issues of religion, ethnicity, immigration (the victim and defendant were recent Jewish immigrants from Poland), and imposition of the death penalty. Using a case study approach to analyze the trial transcript, newspaper articles, and historical accounts of the murder investigation, Rubenstein’s trial, and his incarceration at Brooklyn’s Raymond Street Jail, this article offers a glimpse into the operations of an urban jail in an earlier era when our criminal justice system was in its infancy.