America's Cup Game Changers

How two aristocrats, a boatbuilder, a draper and a tech tycoon made a lasting impact on the pinnacle of sailing.
By John Rousmaniere ,

Because it is so old, unusual, dramatic and controversial, the story of the America’s Cup is often regarded as something out of an exotic Greek myth, with gods arbitrarily reaching down from the clouds to choose a winner and loser. Yet this international yacht competition dating back to 1851 is governed not by Neptune or Zeus, but instead by its competitors and their equipment.

From the days when the America’s Cup Deed of Gift was first announced in 1857 specifying that the races be organized with challenges from yacht clubs, not individuals, and requiring that disagreements be settled through mutual consent (meaning private negotiations with or without a mediator), the racing has become ever more complicated by the sailors’ ever greater ambitions. There have been a few times of transition in which sailors and their backers have altered the fundamentals of the game, a sort of activity that attracts singular and sometimes very difficult figures.

Here are five of them—each, I believe, embodying a comment that writer Bruce Knecht made about one of them, Larry Ellison: “To Ellison, life was an experiment, or a contest, with a singular purpose: determining just how good you can be.”

The Earl of Dunraven (1841-1926) 

Described as “above all, a great Victorian character,” Windham Thomas Wyndham-Quin, Fourth Earl of Dunraven, was a fiercely proud and independent British political figure, an enlightened social reformer and a keen and commanding member of the Royal Yacht Squadron who designed small boats. At a time when the type of yacht competing for the America’s Cup was determined by the challenger, he introduced 120-foot (36.5-meter) racing machines designed by Britain’s leading naval architect, G.L. Watson. The Americans responded with Nathanael G. Herreshoff’s first America’s Cup boats. In 1893, sailing off New York, Dunraven’s Valkyrie II lost the first contest and then, in one of the most exciting events in the sport’s history, led throughout the windy second race before finally being overtaken near the finish by Vigilant.

Lord Dunraven; Valkyrie III’s designer, G.L. Watson; and the yacht’s skipper, Edward Sycamore discuss matters before before a Cup match in 1895.

When an overconfident Dunraven challenged again in 1895, his Valkyrie III lost race one to Defender, and then won race two but was disqualified for a starting line collision. Furious and disappointed, Dunraven withdrew. Later, in England, while giving a speech he carelessly accused the Americans of cheating by altering their boat without permission. A hearing proved the charges specious. Cup racing was put on hold until the genial Sir Thomas Lipton issued the first of what turned out to be his five challenges from 1899 to 1930.

Dunraven left three legacies. His yachts established the sport’s lasting image for spectacle. He correctly observed that the America’s Cup was a whole new type of event, part sport and part nautical proving ground for national status. And his experience proved that no matter how the competitors and their backers behave, the America’s Cup will survive.

Nathanael G. Herreshoff (1848-1938)

Either of the Valkyries might well have won the Cup had their opponents not been designed and built by Nat Herreshoff of Bristol, Rhode Island. He was an MIT-trained engineer and a craftsman whose design method was to apply a whittling knife, sandpaper and his encyclopedic knowledge of boats to a block of pine. The tiny models were turned into yachts, some pretty and fast, others ugly and fast. The 1903 yacht Reliance—with a 144-foot (43.9-meter) length, a 16,000-square-foot sail area and a crew of 66—was as attractive as an I-beam, yet after she overwhelmed Lipton’s handsome Shamrock III in 1903, Lipton snapped, “I don’t want a beautiful boat. What I want is a boat to win the cup—a Reliance.”

Nathanael G. Herreshoff was one of the most influential yacht designers and builders of his—or any—time.

His son L. Francis described “Captain Nat” as a “short-spoken, unsociable man.” Known to throw journalists out of his office, he couldn’t scare away the Morgans, Vanderbilts and other rich yachtsmen who were cut from the same mold. Bristol-built boats were that good. His business was building giant yachts, and he reserved his affections for a few small boats. One was the pioneering catamaran Amaryllis that he built in 1876 and quickly showed her sterns to monohulls. There also was the skiff he and his blind brother Lewis, when they were young, sailed across France through rivers and canals. Nat developed her lines into a sweet sixteen-foot-eight-inch sailing dinghy named Coquina, in which he took quiet, solitary sails—always (of course) within sight of the busy Herreshoff yard.

Harold S. Vanderbilt (1884-1970)

“Somehow or other, Mr. Vanderbilt always won,” my father told me as he reflected on sailing and playing tennis with Harold Vanderbilt. Nicknamed “Mike” for his forceful personality, Vanderbilt loved all games and especially contract bridge (which he invented) and the America’s Cup (which he won three times). An amateur skipper in big boats usually commanded by professionals, he may not have been the most skilled helmsman, but he made up for that by being so well organized that one was always standing by. He sometimes seemed to enjoy the design and build process as much as he did the yachts. “Whether it is sailing, farming, writing books—it doesn’t matter. It is building, creating that interests me.”

Harold S. ‘Mike’ Vanderbilt defended the Cup three times in the 1930s. Here he steers the J-Class Enterprise.

“The low point in my sailing career,” he wrote, was in the 1934 America’s Cup off Newport, Rhode Island. Already two races down to the faster British challenger, his 130-foot J-Class sloop Rainbow was trailing when he handed the steering wheel to a gifted helmsman named Sherman Hoyt, who pulled off the win. His confidence revived, and no longer on the defensive, Vanderbilt altered Rainbow, sailed aggressively and won three straight races along with the America’s Cup. Three years later, he assembled a design team that created the remarkable Ranger, which dominated the Cup as thoroughly as the ugly Reliance had back in the Lipton era.

Brainy, commanding and often ruthless, Mike Vanderbilt could also be deeply sentimental. When his 1930 yacht Enterprise shut down Lipton’s last America’s Cup hopes, he wrote with sympathy in his logbook: “Our hour of triumph, our hour of victory, is all but at hand, but it is so tempered with sadness that it is almost hollow. To win the America’s Cup is glory enough for any yachtsman, why should we be verging on the disconsolate?”

Dennis Conner (1942-)

Dennis Conner was a San Diego draper when we collaborated in the 1970s on a book whose title, “No Excuse to Lose,” expressed his obsession with winning sailboat races. Back then, few would have predicted that he would be the first American to be beaten for the America’s Cup. At Newport in 1983 (in the fourth of his nine tries for the win) he was up against the fast Australia II, with a keel sprouting winglets. In the best-of-seven series, Conner’s Liberty won most of the early races, but Australia II recovered and won the decisive race seven. Conner (representing his hometown San Diego Yacht Club) established an ambitious and successful R&D effort for the 1987 Cup races at Fremantle, Australia. The product, Stars & Stripes, had a clean sweep against the Australian defender. Back home, Conner and his crew were given a ticker-tape parade down Manhattan’s Fifth Avenue and received by President Reagan at the White House.

Dennis Conner won the Cup four times during his illustrious career with the event. He also has the distinction of having lost it in 1983 to Alan Bond’s Australia II while defending for the New York Yacht Club. The club held the Cup for 132 years before the loss.

Soon, corporate sponsors appeared, and they led to salaried sailors. The role that Harold Vanderbilt considered a hobby was rapidly evolving into a business. For Conner, the boat was merely a tool of his trade. “I don’t go down to the dock and pet the boat before I take it out,” he wrote in his book, “Comeback: My Race for the America’s Cup.”

“When I do go out, I thrash the boat around the course. I punish it. I’m likely to crash it into other boats. To me, boats are simply a means to an end, although a boat’s performance has a lot to do with my happiness.” Later, after finally separating from the America’s Cup, he discovered a gentler nautical happiness, restoring classic wooden boats.

Larry Ellison (1944-)

When elimination of most of the America’s Cup nationality rules allowed skilled freelance sailors to move across boundaries, and when the old, heavy keelboats were replaced by livelier and more technically demanding craft, a new type of professional racing sailor emerged from the ranks of Olympic medalists and one-design champions. They helped stimulate more competitiveness and change in the America’s Cup during the past 30 years than occurred during the first 130 years in total. Before 1987, the races were held only in the eastern United States. Since then, such a wealth of talent has spread so broadly that Australia, San Diego, New Zealand, Spain, San Francisco and Bermuda have hosted races.

Software tycoon Larry Ellison shaped the America’s Cup as we know it today with the introduction of high-performance catamarans.

All this time, the stakes were rising and the principals became more aggressive. Disputes between challengers and the America’s Cup holder that used to be settled in quiet negotiation became argued in open court. Some lawsuits were brought by, or against Larry Ellison, the aggressive recruiter of freelance sailors and owner of the current America’s Cup defender, as well as the organizer of this year’s match at Bermuda. Bruce Knecht, who wrote a pair of books about Ellison—“The Proving Ground” and “The Comeback: How Larry Ellison’s Team Won the America’s Cup”—has speculated about why Ellison is drawn to the sport: “The cup involved all of his most motivating hot buttons: competition, money and the application of radically disruptive technologies.”

A sailor for much of his life, initially on San Francisco Bay in small boats and later in ocean racers, Ellison first challenged for the Cup in 2003, when the races were held at Auckland, New Zealand, in America’s Cup Class keel boats, which had replaced the smaller 12-Meters. After winning the cup in 2010 at Valencia, Spain, in an immense trimaran, Ellison hired Russell Coutts, a past cup-winning helmsman for New Zealand and Switzerland, to create and manage the 2013 match in 72-foot high-performance catamarans on San Francisco Bay. One of the best justifications for paying skilled professional sailors well and hiring them fulltime is this type of boat. Like an IndyCar, it is a demanding and unstable high-speed object that teaches lessons quickly—and sometimes brutally.

As the sailors learned how to design hulls so they lifted above the water on foils at speeds of 40 knots or more, the race rules, in anticipation of high-velocity crashes and capsizes, required them to wear impact-resistant clothes and helmets and carry oxygen tanks in case they went into the water. After the death of a sailor and accusations of cheating with a boat’s structure that were true, and after the inevitable disputes about racing rules, the match between Ellison’s Oracle team (flying the Stars and Stripes with just two Americans in the crew) and the New Zealand team produced thrilling racing and an even more exciting narrative. The Kiwis jumped out to a huge lead. Oracle Team USA, its performance improving rapidly with technical adjustments, chipped away and finally won.

Like Conner, Vanderbilt, Herreshoff and Dunraven, Ellison can be criticized for slicing away the romance of the America’s Cup with the sword of ruthless, businesslike ambition, but also like them, he has a soft spot for the Auld Mug. When he came aboard after the last race, instead of sounding off about his achievement, he paid due respect to the event itself, going from sailor to sailor and repeatedly asking, “Do you know what you’ve done? You’ve won the America’s Cup!”

John Rousmaniere is a yachting historian and an authority on safety at sea. He is the author of more than 20 books on sailing and boats including “The Annapolis Book of Seamanship” and “Fastnet, Force 10.”

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