An enslaved man's life reveals slavery's entanglement with the early prison system On December 21, 1811, Prince Mortimer?an elderly, ailing enslaved man believed to be around eighty-seven years old?was sentenced by a Middletown, Connecticut, judge to life in prison for attempting to poison his enslaver by putting arsenic in his chocolate drink. He spent the next sixteen years confined in Newgate Prison, a former colonial copper mine repurposed as a dungeon to serve as Connecticut's first state prison. When Newgate closed in 1827, Prince and the other inmates were transferred to the newly built Wethersfield State Prison. Though designed with reformist intentions, conditions at Wethersfield remained harsh, and Prince died there in 1834 at the reputed age of 110 in a cell just three and a half feet wide. His life?beginning with his capture as a child in Guinea around 1730, followed by more than eight decades of enslavement and over two decades of imprisonment?offers a rare window into overlapping systems of captivity in early America. Despite the paucity of direct source documentation, Denis R. Caron was able to draw on extensive archival research to piece together Prince Mortimer's story by examining the institutions that shaped it. The result is a carefully documented account that will attract readers with such varying interests as African American history, early American law and history, and the development of the American prison system. Through his examination of Prince's life, Caron traces the persistence of institutional unfreedom in a period often associated with liberty and progress.