signed lower right: "J.E. Buttersworth"
oil on canvas
20 x 30 in. (50.8 x 76.2 cm.)

Provenance a private collection
with Quester Gallery, Greenwich, Conn.
the current owner

Vigilant was designed by Nathanael Greene Herreshoff and built in 1893 by the Herreshoff Manufacturing Company of Bristol, Rhode Island. Vigilant was a centerboard sloop with all-metal (steel and bronze) construction. She was owned by a syndicate led by Charles Oliver Iselin and she was skippered by Nathanael Greene Herreshoff. Launched on June 14, 1893, Vigilant beat Colonia, Jubilee, and Pilgrim to win the 1893 American selection trials for the America's Cup defense.

In the 1893 America's Cup Vigilant faced Lord Dunraven's British keel cutter Valkyrie II in a best three out of five races format sailed on alternating courses. The races were sailed October 7, 9, and 13, 1893 off Sandy Hook, New Jersey. In the first race on October 7, in light air, Valkyrie II won the start by 15 seconds and one boat length. At the first mark, Vigilant held a nine-minute lead. Vigilant crossed the finish line 7 minutes ahead of Valkyrie II. In the second race on October 9, Vigilant won the start by 5 seconds, but Valkyrie II worked out to an early lead of 5 boat lengths in a building breeze. By the first mark, Vigilant held a five minute lead and worked out to a 9 minute lead at the second mark. At the finish Vigilant beat Valkyrie II by 12 minutes 30 seconds. In the third race on October 13, 1893, Lord Dunraven, was facing elimination but was certain the Valkyrie II could equal or better Vigilant in the strong breeze. Valkyrie II led the windward leg, but lost a spinnaker at the two-thirds point of the downwind run. At the finish, Vigilant beat Valkyrie II by 40 seconds in corrected time to successfully defend the cup. The World reported it as the fastest race ever sailed, over a course of 15 miles to windward and return under reefed sail and a gale. Vigilant was Herreshoff's first victorious America's Cup design.

In 1894 Vigilant was bought by Howard Gould and became the first America's Cup defender to sail in Europe for the British yachting season. Vigilant raced in the defender trials for the 1895 America's Cup won by Defender. From 1896 to 1910 Vigilant had six different owners the last of whom was William Iselin who sailed her from 1906 until 1910. Vigilant was broken up at a New London junkyard in 1910.