This outstanding figurehead is from one of the most famous racing yachts of all time- George and Franklin Osgood’s FLEETWING. Both members of the New York Yacht Club, the brothers Osgood would own several racing yachts over the years and would compete in America’s Cup races among many others. FLEETWING was part of the regatta that defended the first challenge of the America’s Cup in 1868. However, it was the first transatlantic ocean race for which both men and FLEETWING would be best known.
One night in 1866, over after dinner drinks at New York’s Delmonico’s restaurant, George Osgood and fellow NYYC member Pierre Lorillard debated the merits of centreboard versus keel yachts. FLEETWING was a keel yacht while Lorillard’s VESTA was a centerboard. As the alcohol flowed the debate became more heated, and eventually Lorillard challenged Osgood to prove the superiority of his yacht’s design by racing him to England. Osgood agreed saying they should set off in December in order to get the roughest weather for sailing. Lorillard is said to have replied, “The rougher the better!”
The men set a small wager to cover expenses and within a day word of the race got around to every sporting man in town including fellow NYYC member James Gordon Bennett, Jr. son of James Bennett, founder of the Herald newspaper. Bennett Jr. begged Lorillard and Osgood to allow his yacht HENRIETTA to join the race. The two agreed on the condition that the stakes be raised to $30,000 each- about $450,000 today. Bennett agreed.
Built by Van Deusen of New York in 1865, FLEETWING was 206.1 tons, 106.6 feet overall, 23.8 beam and 11.8 draft. FLEETWING was considered to be of superior design and was the favorite in the race going in.
All three schooners set off from Sandy Hook, Connecticut on December 11, 1865. Only Bennett was aboard his ship though he, like the other two, had professional captains and crews aboard to do the actual sailing. The winter seas quickly turned the race into a battle against the elements. On day two FLEETWING’s jib boom broke, though she continued on. By day four all three schooners were taking on so much water that bailing over took racing. Days of hard weather and skillful navigation followed before Bennett’s HENRIETTA would reach Cowes on the Isle of Wight at the fastest time of 13 days, 21 hours and 55. Both FLEETWING and VESTA would arrive the next day, within an hour of each other, FLEETWING coming in second.
The race was avidly followed by the world’s press, and the drama of the race caught the attention of sporting fans on both sides of the Atlantic. After this yacht racing was seen as a legitimate sport, which continues to thrill fans to this day.
This race and its vessels were painted by all the great maritime artists of the period, including six known works by James E. Buttersworth. We are fortunate to currently also have in our inventory one of the best of these Buttersworth depictions of the race, The Start of the Great Transatlantic Yacht Race which can be found here
The hand painted plaque atop the eagle reads:
Schr. Yacht Ocean Race - Sandy Hook to Needles I.W.
Dec. 11-25, 1866, Stakes $30,000 each.
Yacht : Owner : Time : LAW
Henrietta : J.G. Bennett, Jr. : 13 d, 21 hrs, 55 min : 92
Fleetwing : G.A. Osgood : 14 d, 6 hrs, 10 min : 95
Vesta : P. Lorillard, Jr. : 14d, 6hrs, 50 min : 98
first name :