Colonel John Chester fought gallantly in the Revolutionary War as a lieutenant and later a Colonel. Chester headed a troop of about one hundred select highly skilled soldiers, and fought in the Battle of Bunker Hill until being forced to retreat. In 1776, Lieutenant John Chester was promoted to Major and was one of the first officers to re-enter Boston after the evacuation of the British. Later that same year, he was appointed Colonel to one of the regiments under General George Washington at New York where he fought in the Battle of Long Island. Soon he was made Brigade Commander and continued to fight in many more battles.
Family tradition holds that this sideboard was purchased by Colonel Chester after the Revolution. Apparently it was one of three sideboards made by the same cabinetmaker, and George Washington purchased one at the same time for Mount Vernon.