In December 1866, New York Yacht Club schooners, Henrietta, Fleetwing and Vesta raced across the Atlantic from Sandy Hook to the Needles, Isle of Wight, England, each owner subscribing $30,000, winner take all, "play or pay". This is certainly one of the most famous ocean races in the history of the sport, the likes of which will never be seen again. The race was conceived at a lively October dinner at the Union Club when George Osgood, son-in-law of Commodore Vanderbilt and owner of Fleetwing, with his brother Franklin, discussed the relative merits of Fleetwing versus Vesta with her owner, Pierre Lorillard, Jr. When James Gordon Bennett, Jr. heard about it, he requested and was granted permission to enter, thus making the stake $90,000 winner take all.
Amidst a large fleet of spectator craft the three yachts crossed the starting line on December 11th at 1:00 pm on a cold clear day before a fresh westerly with all sail, including square-sails set. Henrietta and Vesta followed modified great circle courses across the Grand Banks and Fleetwing took a more southerly route. She was the only one of the trio with a cockpit and on December 19th in the worst gale of the race, six men were swept overboard and lost. Henrietta finished on Christmas afternoon after a remarkably fast passage, Fleetwing and Vesta in that order finished early the next day, only a few hours behind Henrietta, making it a close race over such a long course. James Gordon Bennett, Jr. was the only owner aboard his own yacht in this rigorous contest, for which he received much public acclaim and was probably one reason why he was elected New York Yacht Club Commodore in 1871 when only twenty-six years old.