The dark blue hulled "Endeavour II" and the "Ranger" had an even start in the race for the 1937 America's Cup. Both yachts are flying large quadralateral jibs.
The committee boat, "Wilhemina", flying the New York Yacht Club and Race Committee flags, is anchored astern of "Ranger". It is very hazy, a 12 knot wind is blowing and many spectator craft are in position around the course. Sunlight warms the water on the left hand side and a cloud casts a shadow across the foreground.

"Ranger" was the faster yacht to windward and soon pulled ahead of "Endeavour II", rounding the windward mark 4 minutes 13 seconds ahead. This was the fastest 15 mile windward leg sailed in an America's Cup race up to this time. "Ranger" went on to win the race by 4 minutes 27 seconds. She also won the fourth race and thus the America's Cup.

Both Olin and Rod Stevens raced on "Ranger", with Harold Vanderbilt on the helm. "Ranger" was designed by Starling Burgess, with assistance from Olin Stevens. She was the most successful "J" Class yacht in history winning 32 of the 34 "J" Class races of the 1937 season.