Olin James Stephens II (April 13, 1908 – September 13, 2008) has been described as the best-known and most successful yacht designer of the 20th century. Stephens was born in New York, but spent his summers with his brother Rod(erick) learning to sail on the New England coast. He also attended the Massachusetts Institute of Technology for a term.
Olin Stephens' name is well known in connection with the America's Cup, as he assisted W. Starling Burgess on the J-Boats of the late 1930s, including Ranger, which won the America's Cup in 1937, defeating the Royal Yacht Squadron's Endeavour II in four races. In addition, he helped design six twelve-meter defenders which made up all the defenders that won the America's Cup from 1958 with the Columbia to 1980 with the Freedom, with the exception of the Weatherly in 1962. All this time he was producing successful racing boats, including the winners of a total of eight of the nine America's Cup matches between 1937 and 1980. Other than Ranger, the most remarkable of these boats was Intrepid, the defender in 1967 and, after alterations by Britton Chance, Jr., again in 1970. She had a rudder separate from her keel to reduce wetted surface and improve steering. The separate rudder was not new, but Stephens made it work on a number of increasingly large ocean racers, most notably Thomas Watson's state of the art Palawan III, in the mid-60's before successfully using it on Intrepid.
Olin Stephens has also designed many successful off-shore and stock boats, including the Dark Harbor 20, which he designed in 1934. His brother Roderick Stephens was also a partner in the renowned yacht-designing and yacht brokerage firm Sparkman & Stephens, specializing in supervision and testing of yachts designed by the firm. Olin was working in the Nevins shipyard in 1928 as a draftsman when he first met yacht broker Drake Sparkman. They together set up an office next door to Nevins in 1929. Since retiring from the company he lived in Hanover, New Hampshire, where he spent his final years writing computer programs for designing yachts. He was awarded the Nathanael G. Herreshoff Award by the North American Yacht Racing Union in 1965 for his contributions to sailing.
Olin Stephens was also involved in ocean-going sailboats. His yawl designs Dorade (1929) and Stormy Weather (1934), his favourite design, each won the Newport Bermuda Race and the Fastnet race several times. Olin and Rod Stephens were accomplished yachtsmen. They were members of the winning crews of Dorade and Ranger. Olin served as tactician and navigator, while Rod trimmed the rig and sails. In the 1960s and 1970s, Olin contributed to the luxury yacht builders Nautor Swan of Finland and Hallberg-Rassy of Sweden.
In 1993, Olin Stephens was inducted into the America's Cup Hall of Fame. Several years later, in 2000, he wrote the autobiography All This and Sailing Too. In 2007, he was named as one of six inductees to the inaugural ISAF Sailing Hall of Fame. He was ranked member number 1 on the New York Yacht Club Member Seniority List at the time of his death. Their tribute and profile can be found at http://nyyc.org/home/article_193. In 2008, he celebrated his 100th birthday and died exactly five months later.
- Jones, Gregory O. The American Sailboat. October 1, 2001. MBI Publishing Company, p. 16. ISBN 0-7603-1002-5.
- The Dictionary of Nautical Literacy. McGraw-Hill Professional, p. 356. ISBN 0-07-141950-0.
- Rousmaniere, John. Desirable and Undesirable Characteristics of the Offshore Sailing Yacht. May 1, 1987. W. W. Norton & Company, p. 18. ISBN 0-393-03311-2.
- http://sailing.org/halloffame/21220.php (article mentioning his early years and education)
- Dorade: photos
- Stormy Weather: photos
- Website: Sparkman & Stephens Inc. (S&S)
- http://www.sailing.org/22732.php (article highlighting his 100th birthday, with a picture)
- Daily Sail Obit
- Sailing World Obit
- NY Times Obit
-  (Dolphin24.org)