Born in Stamford, Connecticut, he forfeited 202,000 ha near Albany, New York, by taking up arms for the King on the outbreak of the American Revolution. He raised the Loyal (Jessup's) Rangers and served under Burgoyne. This corps was disbanded at the end of the war, its members settling in the present Leeds and Grenville Counties, and on the Bay of Quinte. In return for his services, Jessup received extensive lands from the Crown. In 1810 a townsite was surveyed on this grant which he named after Robert Prescott, Governor-in-Chief of Canada, 1797-1807.