Enslaved by a series of prominent Saybrook residents during the mid to late 1700s, Tamar would see two of her children sold away from her and her own promise of freedom disappear when her enslaver died in debt and she was sold to someone else. In 1774, her labor was the focus of a legal dispute between John Kirtland and Samuel Whittelsey, who both claimed rights to her time and labor. As a result, Tamar and her young daughter, Phillis “about two or three years old,” were “attached” while the dispute was being settled. Within a few years, apparently facing financial woes, Kirtland had sold Phillis to Samuel Hart. In 1785, Kirtland sold Tamar’s daughter, Rose, to Gen. William Hart, Samuel Hart’s brother. Shortly after, in 1787, Kirtland died. To help settle Kirtland’s debts, his heirs sold Tamar and her infant son, Cato, to Gen. Hart. Other than Phillis, who was enslaved at a Hart house down the road, Tamar’s family was at that point reunited, and soon Tamar would welcome another child into the household, Cyrus. The records do not tell us when or how Tamar died, but her children, and especially her daughters, Rose and Phillis, lived long and relatively well-documented lives. Both are remembered in newspaper obituaries and on their grave markers which stand next to each other in Cypress Cemetery. Tamar and her two daughters are also united with three Witness Stones markers installed in a small garden at the Gen. William Hart House.