Stevens’s challenges for one-on-one match races—except one lone client of his railroad business. The squadron’s caution occasioned the Times of London to accuse the club’s members of behaving like pigeons paralyzed by the appearance of a sparrow hawk.

There was, however, one squadron race open to America —a fifty-three-mile circumnavigation of the Isle of Wight on August 22, 1851. The prize was a bulbous silver ewer called the Royal Yacht Squadron £100 Cup. The British exempted America from several rules that might have prejudiced her. She also was a little lucky. Because she inadvertently received the wrong race instructions, she sailed a slightly shorter course than her competitors, a few of the best of which were damaged or otherwise forced to quit the race. But her luck was winner’s luck. Faster on every point of sail, America stretched out to a lead of more than seven miles. Night was falling as she crossed the finish line, and her competitors were somewhere back in the murk. The Times later reported the following exchange between two spectators:

“Is the America first?”

“Yes.”

“What’s second?”

“Nothing.“

That may be the source for the America’s Cup’s most enduring legend, which has it that Queen Victoria, watching the race with Albert from the royal yacht, asked who was second, and a deckhand answered, “Madam, there is no second.”

America also won her single match race, and Stevens was making plans to take her to London when an Irish nobleman offered to buy her at a price providing a nice profit. That unsentimental transaction completed, Stevens and his friends went home with the ewer, which came to be called by the name of its first winner.

Stevens arrived in triumph. “Like Jupiter among the gods, America is first and there is no second!” exclaimed Daniel Webster. Britain’s reputation as the monarch of seafaring seemed shattered, and by a yacht carrying another country’s name. Subsequent events might have taken a different path had Stevens named the schooner for his hometown, Hoboken.

Soon after Stevens’s death, in 1857, the surviving syndicate members turned the trophy over in trust to the New York Yacht Club, with a Deed of Gift dedicating it for use as “a perpetual Challenge Cup for friendly competition between foreign countries.” A challenge to the cup’s holder could come only from a yacht club from another country, and competitors should negotiate terms (for example, the schedule of races and the types of boats to be sailed).

The first challenger, in 1869, was an Englishman, James Ashbury. Like Stevens, he expected a match, but when the contest was finally held in 1870 he got a fleet race, in which his Cambria was badly

beaten. The winner was a schooner named Magic. Over the next twenty-five years there were eight true one-on-one matches, two involving Canadian boats and the rest British challengers. Most of these races were exciting just because the hundred-foot-or-larger boats were so imposing, with their towering rigs, but a few were thrilling because they were close. One of the most gripping races in all cup history was the final one in the 1893 match between the challenging Valkyrie II, owned by the Earl of Dunraven, and Vigilant, the first of five cup defenders created by Nathanael Herreshoff, of Bristol, Rhode Island.

In a fresh 25-knot easterly breeze that had both boats deeply reefed, Valkyrie walked away at the start and built a two-minute lead in fifteen miles of beating to the windward mark, almost obscured by the huge spectator fleet and the black smoke billowing from their stacks. She rounded the stake boat, headed back to the finish, and, the fierce wind now at her stern, set her spinnaker, which promptly tore to shreds. Behind her Nat Herreshoff, in command of Vigilant, also set a spinnaker. Then he went about the risky job of shaking out his reefs. One of his crew of seventy climbed onto the boom and, with a taut halyard tied around his body to keep him from falling into the water, crawled ninety feet to its end, cutting the reef points. Valkyrie meanwhile kept her reefs in and blew out her second spinnaker. Vigilant, her mast shaking wildly, raced by at twelve knots to win by two minutes and take the series, 3-0.

Although challengers sometimes came close, they won only three races in the first thirteen matches. Even when fast and ably sailed, they labored under several disadvantages. Their boats had to be heavier to survive the long voyage to New York that was required before a ruling in 1956 allowed them to be shipped on freighters. Because the races were held on the defender’s course, the conditions were often unfamiliar. The challengers also had to submit to the New York Yacht Club’s sometimes arbitrary authority in assigning handicaps and deciding on-the-water disputes. Still, sailors kept coming, drawn, then as now, by challenge, patriotism, and spectacle.

The cup was a spectacle and a spectator sport long before it was covered by television. A greater proportion of the potential audience watched the races in person a century ago, when New York’s population was only two million, than does on television today. Public interest was fueled by the vast population of Irish-Americans in New York who fervently hoped for the defeat of English challengers, and the media fed this interest. Mass-circulation newspapers covered the cup even more thoroughly than they did

baseball; the first use of the wireless telegraph was to report cup races from the water; and Thomas A. Edison sent an early motion-picture crew out on a spectator boat to film a race in 1899.

When crowding made the New York Bay course dangerous for competitors and audience alike, the races were moved out into the Atlantic off Sandy Hook, New Jersey, but with little effect. Even out on the rolling ocean, the course was lined with big passenger and ferry boats packed to the rails with thousands of paying spectators. They were entertained by brass bands blaring patriotic anthems—American, Irish, or British as suited the patrons. The spectator fleet sometimes wandered onto the course, prompting racing crews to display signs reading KEEP AWAY. By 1899, the crowding was so bad that the Navy had to provide patrol boats to manage the traffic. In 1930, the races decamped to Newport, Rhode Island, but even there a thousand or more spectator boats could be counted on.

The excitement was as great for the owners as for the crews and onlookers. J. Pierpont Morgan, who helped finance several of the hundred-thousand-dollar-plus defenders, was no sailor, but after his Columbia won in 1899, he hefted his bulky frame aboard the sloop from a launch and, according to the New York Tribune, threw his arms around another syndicate member “with a shout of delight…and danced about with joy.”

That moment almost did not come about. In 1895, after the Earl of Dunraven lost his second match, he nearly ended cup racing altogether when he accused the Americans of cheating. Hearings revealed Dunraven’s case to be circumstantial at best, but the nasty controversy and accompanying outsized nationalistic feelings appeared to doom the contest. “For the sake of peace and quietness, such events as races for the America’s Cup are rather to be deprecated than otherwise,” the Times of London editorialized.

The fact is that “peace and quietness” have rarely surrounded the America’s Cup over its long history. The event needs public passion. The best people involved with it have always succeeded in stirring things up without an excess of rancor, and the very best of the best was Sir Thomas Lipton.

Lipton broke the post-Dunraven funk when he challenged from Northern Ireland in 1899. He returned four more times over the next thirty-one years. His sole failing was that he never won the cup. Everybody loved him, and almost everybody wanted him to win; because of this, the America’s Cup thrived. So did Lipton’s international tea and grocery concern, leading a British journalist to call Lipton’s challenges “virtually the finest advertising stunts the world has ever known.”

In his third match, in 1903, Lipton came up against the second of six cup superboats (America had been the first). This nautical version of Secretariat and Joe DiMaggio’s Yankees was Herreshoff’s Reliance. Stretching half the length of a football field from

the tip of her bowsprit to the end of her boom, she carried more than a third of an acre of sail and had a hull so delicate that a rough sea could dent the bow. Under way, her huge sails teetering over her low hull, she looked like an immense tightrope walker. After the slaughter, people tried to console Lipton with assurances that at least his Shamrock was the prettier boat. “Give me the homeliest boat that was ever designed, if she is like Reliance,” he snapped back. Lipton got his ugly boat for the next match in 1920. Shamrock IV won two races but found no way to win the necessary third.

Lipton had one challenge left in him for what he called “the Auld Mug,” but that, too, ended badly. The world’s profound affection for the old merchant-sportsman reached even to his hard-boiled final opponent, Harold S. Vanderbilt, owner-skipper of the defender, Enterprise, in 1930. Near the end of their last race, with Shamrock V well astern, Vanderbilt handed the helm to a shipmate and went below. “Our hour of triumph, our hour of victory, is all but at hand,” Vanderbilt later wrote in the log, “but it is so tempered with sadness that it is almost hollow.”

Harold Vanderbilt competed in three matches in the 120-foot-plus J-Class yachts in the 1930s and won them all. Wealthy enough to pay his way and more, he was even more valuable as a brilliant organizer of men and equipment. He also was an innovator who constantly pushed his technical advisers in new directions, including using experimental materials that would later influence all sailboats (he bought the first synthetic sails for the races).

For the 1937 contest, he undertook a program of testing design ideas with small models towed in a tank at the Stevens Institute of Technology in Hoboken. His design team, the veteran Starling Burgess and the twenty-nine-year-old Olin Stephens, came up with the third of the cup’s superboats, Ranger, the first of Stephens’s six cup defenders. She compiled a 32-2 record with an average winning margin of a mile and easily won the match. Five years later, she and most of the others were broken up, the steel in their hulls and the lead in their keels gone to war.

“It is a game for the wealthy, so let them choose the type and size of craft,” Nathanael Herreshoff once said of the America’s Cup and its vessels. Because of high taxes and inflation, wealth meant something different after World War II. Cup competition remained dormant until the Deed of Gift was altered by the New York courts to permit more economical boats of the 12-Meter Class (the name referred to their measurement under a handicap

rule), with crews of eleven amateurs instead of the twenty-five professionals that had been standard. The first of the new-style matches was held in 1958, when the American Columbia easily beat the awkward British Sceptre.

The chief competition now came from Australia, which first challenged, in 1962, with Gretel, a fast boat belonging to the publisher Sir Francis Packer. The skipper of the American defender, Weatherly, was the talented and shrewd Emil S. “Bus” Mosbacher. Normally the most aggressive man on the course, he realized that this time he had to lay off and try to win by his wiles. His strategy worked, yet sometimes Gretel was simply too fast. In the second race,  Gretel caught a huge wave and surfed by as her crew shouted war whoops. In the fourth race the Australians were moving up so rapidly that Mosbacher, hoping that they did not know where the finish line was, tried to lure Gretel off course onto a slow point of sail. She fell for the trick, and Weatherly held her off to win by only twenty-six seconds. In 1967 (after another American crew had won an easy victory over the British in 1964), Mosbacher made sure to return in the fastest boat. Designed by Olin Stephens with a radical keel separated from her main rudder and with almost all her crew belowdecks, Intrepid was another America’s Cup superboat. She beat the Australian challenger Dame Pattie by an average of more than four minutes, or half a mile per race.

In 1970, the America’s Cup underwent four changes whose cumulative effect, while not obvious then, was to transform competition and lead inevitably to a challenger’s win. First, a generation willing to spend far more money arrived on the scene. Also that year, the New York Yacht Club accepted a second challenge from the Packer syndicate with Gretel II and, more important in the long run, one from the French manufacturing tycoon Baron Marcel Bich, the man behind the Bic pen.

Second, because there were two challengers, the boat that ultimately sailed against the defender was honed by close combat in elimination races.

Third, in 1970, the Americans for the first time came to seriously question their technology. The New York Yacht Club had usually been at the forefront of most developments, from yacht design to construction using space-age materials like titanium. But that year the model testing system that Americans had developed to a high exactitude somehow misled their designers into producing slow, lumbering hulls.

And fourth, an extremely aggressive public relations campaign on the part of the challengers began to shift control over the event away from the New York Yacht Club.

Although the trimmer Gretel II had a speed advantage over the redesigned Intrepid, she lost the match because her crew simply did not sail well. They

won the second race easily but were later disqualified by the New York Yacht Club’s race committee for colliding with Intrepid at the starting line. Though in the wrong on the rules, the Australians won the public relations battle. “An Australian skipper complaining to the New York Yacht Club is like a man complaining to his mother-in-law about his wife,” Frank Packer insisted in one of his more colorful protests. Gretel did win one race and came close to winning two more, but in the end her crew either did themselves in or were outsmarted by the American skipper Bill Ficker. The dispute put the New York Yacht Club on the defensive for the first time, and it finally relinquished some of its authority over the cup by appointing an independent international jury to decide fouls.

Power was being defused in other ways too. A new method for financing defenders arrived in 1974. The money for a cup campaign would now be raised not from a small number of millionaires, all New York Yacht Club members and friends, but from thousands of people, through tax-deductible donations to foundations or educational institutions that owned the boats. By 1980, the American skipper Dennis Conner could confidently declare, “I have 300 million Americans to represent. I have a lot to think about, and I don’t want to let them down.”

The defenders’ $1.5 million budget that year looked skimpy compared with the increasing outlays by the Frenchman Bich and a growing band of challengers, including Sweden, Canada, and Italy as well as Britain and Australia (in time Japan, Spain, Switzerland, and Russia would also challenge). The Swedes, in 1977, developed the “industrial challenge,” in which Volvo and more than sixty other Swedish companies supplied money, technology, and research. Not unlike America in 1851, Sverige was intended to show off her country’s technology in the international trade fair into which the America’s Cup was rapidly evolving. The difference lay in the now blatant commercial interest. Other competitors asserted their own financial goals. Alan Bond, a Western Australian real estate developer, said that he challenged four times between 1974 and 1983, partly because Newport offered an excellent opportunity for making contacts and doing business. “Successful men come to the America’s Cup to be with other successful men,” he said.

By 1980, the America’s Cup was the sailing equivalent of the arms race. Defenders and challengers alike ran full-time multi-year testing programs and demanded a new level of commitment from crews. “The days when a New York stockbroker will leave his business for a month or two and race in the America’s Cup are over,” declared Nat Herreshoff’s grandson Halsey, who often sailed in cup boats. The last amateur skipper of an America’s Cup winner was Ted Turner, who took a few months off from his broadcast company in 1977 to sail (and win in) Courageous .

After that a new type of professional sailor took over. The forerunner was Dennis Conner. The most successful racing sailor of his generation, he will have sailed in all eight cup seasons between 1974 and 2000, and has won four times. He came up through the ranks of yacht-club organizations but eventually became independent, forging his own alliances with corporate sponsors and media companies to create his own racing entity, Team Dennis Conner.

In the 1970s, Conner and other Americans cut back on basic research on boat design; after the problems with small models in 1970 and again in 1974, they used large models but fewer of them. Conner, apparently deciding that naval architecture had gone as far as it could go, concentrated months at a time on developing superb crews and fast sails. But the challengers stayed focused on design innovations. In 1980 the British developed a curved mast that permitted a larger mainsail. The idea was copied by the Australians for the match against the defending Freedom. Australia had a speed advantage that won it a race, but Conner used unorthodox tactics (as skippers of slower boats had done before) and prevailed, 4-1.

The challengers could see the prize on the near horizon. Alan Bond, in three increasingly effective matches, had learned the lessons of tight organization and advanced technology. Like Thomas Lipton, he was a master of public relations, but where as Lipton’s public presence had been soothingly benign, his was aggressively sharp-edged, aimed at keeping the New York Yacht Club on the defensive. Behind this screen, Bond in the early 1980s put together a multimillion-dollar campaign whose lead designer, Ben Lexcen, conducted research on keels at a model towing tank in the Netherlands. The result was the 1983 superboat Australia II, which carried a novel, highly efficient keel with winglets under a small, light hull designed to perform in the gentle winds that had come to prevail off Newport. Olin Stephens, now retired, congratulated Lexcen on the success of his work, but the New York Yacht Club challenged the keel on several fronts. When Bond presented an angry public counterattack, the club briefly considered canceling the match altogether.

Australia II, raced by John Bertrand, swept the challenger eliminations but had a much tighter series against Conner’s Liberty. Sailing brilliantly, Conner overcame the speed difference to gain a 3-1 lead, but damage to his mast and some chancy tactics cost him two races. Liberty led the rubber race until halfway down the fifth of the six legs. On a run square before a dying breeze—the conditions that the challenger was designed to excel in— Australia II gained rapidly. Conner jibed away to look for wind, but Bertrand swept by to win the race and the cup. The world’s longest winning streak ended on its twenty-fifth challenge, and the cup went to Perth, Australia.