In 1743, Jonathan and his older brother Othniel cleared land in Charlemont, Massachusetts, and built Taylor's Fort there in 1754. By 1760, he was living in nearby Heath, Massachusetts.
In 1746, Jonathan bought shoes for Prince, who was probably enslaved by him. That same year he also borrowed money from Joseph Barnard to pay "Sharp", which refers to a man of African/Indigenous heritage who was known as "Sharp Caleb" and "Caleb Sharp." In 1771, Taylor purchased an enslaved man named Titus from Daniel Arms of Deerfield. He paid 20 shillings. (Healy, Allan, Charlemont, Massachusetts, 1765-1965)
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