John was thirteen years old when he moved to South Carolina and soon after he entered the mercantile business house of Colonel John Kershaw in Camden as an apprentice beginning his career as merchant at the expiration of his apprenticeship. By 1776 he was a member of the firm which had extensive and progressive branch stores throughout South Carolina. In 1765 he was appointed Inquirer and Collector for St. Mark. By the time of the Revolution his landed estates were very large. He was a delegate to the first Provincial Congress, which met in Charleston, South Carolina in 11 January 1775 and again on June 1st, of the same year he was elected the Committee of Continental Association. He was appointed "Justice of the Quorom" of the Orangeburg District in 1775, Justice of the Peace in April 1776 and was Paymaster, with the rank of Captain in the Third Carolina Regiment at the beginning of the Revolution, but a severe attack of rheumatism compelled him to resign. Recovering after the war was over he was prominent in politics, and in 1788 a member of the convention to frame the Constitution. He went to the State Senate twice, and was among the first election of trustees for the new South Carolina College. His intimate friends were leaders of the day, and among them were Charles Gotesworth Pinckney, Governor John Rutledge and Colonel Wade Hampton. John Chesnut was a very rich man, he owned numerous houses, giving a weekly ball an supper. He often traveled in a coach and four to Charleston or Columbia in the winter and rarely missed a visit to Virginia and Philadelphia or New York during the summer, traveling with servants and horses taking at least a month for the journey. He was well educated and had a fine library. During President Washington was taking a tour of the South during his first term, Washington was entertained by John Chesnut, and in the family archives was a letter from the president to his host, in which he describes the uses of "one of my drill plows," which he was sending Chesnut, as he had promised. On the walls of the hall at Mulberry hung a portrait of Washington by Gilbert Stuart, along with portraits of John and his son James and his wife, by the same painter. The portrait of John Chesnut was owned by his great grandson, David Rogerson Williams III.
John was born at
Shenandoah Co., Virginia, on 18 June 1743. He was the son of
James Chesnut and
Margaret Cantey. He married
Sarah Cantey at
Camden, Kershaw Co., South Carolina, in 1770. John died on 1 April 1813 at
Camden, Kershaw Co., South Carolina, at age 69. His body was interred in April 1813 at
Kershaw Co., South Carolina. Buried in the family buring ground at Knight Hill..