The painting depicts the "Volunteer" running under spinnaker towards the "Thistle", who is still beating towards the windward mark. Clouds cast deep shadows on the water in the foreground and a patch of sunlight spotlights the racing yachts. Rain squall clouds follow astern of "Volunteer." The challenger "Thistle" is plunging through the waves as she battles to windward in the fresh breeze. She is carrying her topsail but it would be debatable wether she would sail faster if she had taken it down and then set it again on the run to the finish. In a fresh Easterley wind on September 30th 1887, the yachts raced 20 miles to the windward mark followed by a 20 mile run to the finish off Sandy Hook, New York. "Volunteer" rounded the windward mark 15 minutes ahead of "Thistle", but "Thistle" gained on the homeward run, with "Volunteer" winning by 12 minutes and taking the America's Cup. "Vounteer" at 106 feet on deck was designed by Edward Burgess and built for a Boston syndicate at Wilmington. "Thistle" at 108 feet on deck was designed by George Watson for an English syndicate.