The painting depicts the scene as it may have looked from the transom of Yankee, on one of the races in Long Island Sound, in the first summer of the J Class. With Weetamoe to the left and Whirlwind to the right. On the far left is J.P. Morgan's motor yacht Corsair and on the far right Mr. Vanderbilt's motor yacht Vara.

America Cup defence contenders 1930 sailing in Long Island Sound

In 1930 four syndicates called on the cream of American designers to create contenders for the honour of defending the Cup. Enterprise came from the drawing board of W. Starling Burgess and was built at the Herreshoff yard in Bristol. Her sponsors were a group of seven including Winthrop W. Aldrich, Harold S. Vanderbilt, Vincent Astor, and George F. Baker, Jr.

Junius S. Morgan and George Nichols formed a group to finance Weetamoe, designed by Clinton H. Crane and also built at the Herreshoff works. Paul Hammond, Landon K. Thorne and George M Pynchon engaged L Francis Herreshoff, son of the famous "Nat", to design Whirlwind for construction at the Lawley yard in South Boston.

And in Boston the fourth group, headed by John S. Lawrence and Charles Francis Adams, went to Francis C. Paine, whose forebears were responsible for Puritan, Mayflower and Volunteer, to design Yankee, also built by Lawley.

All four would be racing against each other along with Resolute and Vanities in the summer.

Enterprise, Yankee, Weetamoe and Whirlwind were launched in April and May 1930. Variations in their measurements were slight, less than one per cent in sail area. Designers' individuality was evident to the practiced eye above the waterlines. All the boats had steel frames with bronze plating, except Whirlwind, which had a double-planked wooden hull. Below decks they were bare, all bulkheading omitted. Instead of having the spacious furnished staterooms and quarters of earlier boats they were fitted with winches, racing gear, and lockers for the many sails they used. Above decks they were not unalike.

On June 17th the four 'J' boats, along with Vanitie and Resolute, met for the first time midway between Mattinicock Point and Peningo Neck on Long Island Sound for a 23.1/2 mile triangular race. It was the beginning of a long struggle that lasted through ten weeks. Before the defender was chosen, five series and twenty-seven races tested the contenders in all kinds of weather. Weetamoe, skippered by George Nichols, won the first race in which all four contenders participated. For the rest of the season, it was a hard fought duel between Nichols in Weetamoe and Vanderbilt in Enterprise.

The final trials, sailed over the same Newport water where the Cup races were later held, started on August 20. After two races in which the contenders were paired. Enterprise with Weetamoe, Yankee and Whirlwind. Enterprise was chosen to defend. During the second race Vanderbilt set an all time record for the 30 mile course, averaging 10.64 knots.