Jonathan Ashley was born in Westfield, Massachusetts, and entered the ministry after graduating from Yale College in 1730. From age 20 until his death in 1780, Ashley served as the first minister for Deerfield, Massachusetts, his first and only parish. His liberal theology was typical for the region in contrast to the more radical theology of the Reverend Jonathan Edwards, the minister in nearby Northampton, Massachusetts. Ashley's conservative politics subsequently placed him at odds with Deerfield's Whigs (Patriots) at the time of the American Revolution (1775-1783).
Ashley and his wife Dorothy had nine children, six of whom survived to adulthood. Boarding and tutoring young men in Latin and Greek in preparation for the required entrance exams at Harvard and Yale provided an additional source of income but also increased the work of running a large household.
The Ashleys enslaved three people: Jin (Jenny) Cole (ca. 1722-1808), her son Cato (1738-1825), and Titus. Ashley purchased Jin and Cato in 1738. He bought Titus from the Reverend Samuel Kendall of New Salem, Massachusetts, and sold him ten years later, in 1760. Both Cato and Titus performed mainly agricultural labor. Ashley also made money by renting them out to work for other local farmers. Both men served in the French and Indian Wars (1754-1763). After Ashley's death, Jin and Cato remained with Ashley's widow, Dorothy. Jin and Dorothy died three weeks apart in September 1808, after which Cato lived with Ashley's eldest surviving son, Elihu. According to Deerfield's town historian George Sheldon, the Ashley family ceased holding Cato in slavery after Massachusetts ratified its state constitution in 1780, but he remained a servant in the Ashley household until his death in 1825.
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