One of the finest yachts of the 19th century, DAUNTLESS was built as the 97 foot sloop L'HIRONDELLE in 1866 by Forsyth & Morgan at Mystic, Connecticut for S.D. Bradford Jr. A year after launch she was sold to publisher of the New York Herald and member of the New York Yacht Club James Gordon Bennett Jr.

Bennett was famously a serious yachtsman and also something of a rogue. He was as much news maker as publisher and tales of his drinking, lavish spending and carousing were often in the papers.

Soon after acquiring L'HIRONDELLE Bennett commissioned John B. Van Deusen to redesign her, lengthening the yacht to 120 feet and rerigging her as a schooner. Renamed DAUNTLESS, she was introduced to the New York yachting scene that same year.

Here we see DAUNTLESS at the start of that 1867 racing season making a striking debut in the waters off Manhattan's Castle Garden. Along with the NYYC burgee she still flies the private burgee of her former namesake, a white l'hirondelle, or swallow, on a blue field, of course with a swallowtail. Buttersworth painted DAUNTLESS many times, but rarely with this flag, and both the setting and the details of the work tell the story of one of the great 19th century America's Cup yachts at the start of her career.

The painting sets off the reborn yacht perfectly, with a dramatic sky letting in shafts of light that illuminate the landmarks and the ship itself. At her bow, two US Navy Ships sit at anchor while in the distance we can make out two paddlewheelers at the vessel's stern. Buttersworth has given DAUNTLESS a slightly exaggerated reflection to create more interest in the water, a key characteristic of his work in this period.

DAUNTLESS went on to have a long and storied racing career. She would defend the America's Cup in 1870 and would go on to become the flagship of New York Yacht Club. She is considered by some as the most famous sailing yacht of the 19th century, often entering races with a reputation of being nearly invincible.