Ishmael was one of seven children of Arthur and Joan Prutt, who were enslaved by Isaac Chauncey (1670-1745) of Hadley, Massachusetts. He was born in January of 1726. (Town records, 1659-1719, Hadley, Massachusetts. See also James Avery Smith, History of the Black Population of Amherst, Massachusetts (Boston, MA: New England Historic and Genealogical Society, 1999), pp. 110-111.)
Entries for Ishmael appear in the account book of Samuel Gaylord, of Hadley. Between 1782 and 1787, he purchased a penknife, clothing and shoes, had shoes repaired, and borrowed a horse and cash. On at least one occasion he paid his bill by working for Gaylord. (Account book of Samuel Gaylord, Historic Deerfield LIbrary, Deerfield, Massachusetts.)