Cuff was enslaved at the Whitfield House in Guilford from 1772 to 1775 by Joseph and Sarah (Ruggles) Pynchon. He was a gardener and teamster and later may have served in the Continental Army during the Revolution. The first known owner of Cuff was Thomas Ruggles Jr, pastor of the First Congregational Church in Guilford. In Ruggles’ will, he lists Cuff as “moveable” item in his estate, writing about “all the remainder of my moveables, (Except my Silver Tankard Silver Teapot Gold Seal Ring Library & wearing apparel Husbandry tools and Negro Servant Cuff).” He also prescribes that the individual inheriting Cuff must ensure that “he be Comfortably Taken care of & Provide for During Life by my Heir.” In addition, Ruggles ordered that Cuff remain in the household of his daughter, Sarah Ruggles Pynchon, and her husband, Joseph Pynchon, until their son, Thomas Ruggles Pynchon, comes of age, at which point Thomas would inherit Cuff. This arrangement meant that while his son was still young, Joseph Pynchon was able to “rent out” Cuff to neighbors. One who took up the opportunity was Eli Foote, grandfather of Harriet Beecher Stowe.