September 07, 1958

The portrait gallery which starts on the opposite page sketches in line and prose 10 men, each of whom in a particular way contributed to the century-long history of the famous yachting trophy, the America's Cup. The history of any great trophy is not only a matter of the statistics of victory and defeat, but also, and primarily, it is a human record. It is perhaps enough to know about the America's Cup that it was won in an English regatta in 1851 by the schooner America; that after nearly being melted down for inscribed medals it was pulled from a carpetbag half-forgotten in a Greenwich Village townhouse in 1857, and deeded to the New York Yacht Club as a challenge cup open to challengers from foreign countries; and that 16 times British yachtsmen have challenged for the cup and on each occasion have gone away empty-handed—a remarkable testimonial to American yacht-racing skill.

But it is the men involved in competition for the cup who have made its history one of the most colorful in sports—a history always flamboyant, and marked with competitive spirit at its highest. They spent freely, even prodigally, of their time, their money and their energy to build sailing craft which were the finest in the world, in which to compete on open ocean waters for a trophy which through the years assumed the status of a legend—and thus they acquired, each to some degree, something of a legendary character themselves.

The bettor who started it all
He was the son of a Hoboken family of railroad pioneers, the playboy of the family, a fancier of cricket (he tried unsuccessfully to introduce the game in the U.S.), a gambler who wagered as much as $10,000 on a horse race, the founder of the New York Yacht Club in 1844 and, in 1850, the organizer of the syndicate which built the schooner America, for which the cup was to be named. His motives in ordering the yacht were twofold. As a keen competitor he felt compelled to accept the British suggestion that this country send abroad a representative of American nautical skill; as a gambler (in those days cash bets running to thousands of dollars were an accepted adjunct to yacht racing) he thought any investment would be returned many times over. Unhappily, the first sight of his rakish craft in English waters discouraged not only all betting but almost all racing; the only tangible return to Stevens' investment was the famous silver pitcher, worthless as a container, being open at both ends, and valued at perhaps $40 on the bullion market. It scarcely augured its momentous role in history.

A seasick builder with a passion
He seemed to have none of the attributes one would expect of the yacht designer. His great love, the sea, treated him roughly: he was made seasick by the slightest swells; to compound his miseries, he could never leave New York Harbor without suffering extreme pangs of homesickness and while he traveled to England aboard the famous yacht which he created, the trip was torture for him. Yet he had a passion for yachts; he was only 10 years old when he built his first boat—a scow so dangerously unseaworthy that his older brother destroyed it. He was just into his 30s when he designed and built America, staking his career on the bold concept of her lines, absorbed in her, spending his off days adzing and smoothing the surfaces of her hull. She was so fast that after her victory around the Isle of Wight a rumor swept the Solent that she had a propeller. Curious sightseers in rowboats circled her stern. "I would not wager a guinea against the Yankee craft," said a famous clergyman, "but I will give a hundred to see her bottom"—an unintentional tribute to the remarkable genius of her young designer.

The dandy who evened the odds
The first challenger for the cup, John Ashbury was a tall, pale man with a habit of running delicate fingers through his beard, a dandy who bathed every night before dinner—to the vast suspicion of the Saturday-night-bathing American public. The New York Yacht Club looked upon him with equivalent suspicion which mounted, eventually, to horrified indignation. Able to thwart Ashbury's first challenge in 1870 by sending a fleet of 23 yachts against him, they found themselves recipients of such a storm of letters, counterplots and threats from the outraged Englishman that they were forced to bow to him and permit his second challenge, also unsuccessful, to be run as a match race between two yachts much as it is today. The change was not made gracefully. Ashbury's letters were so vindictive that the New York Yacht Club returned three trophies he had donated. Despite his methods, however, his determination to even the odds between defender and challenger was the first great shaping force in the cup's history.

Protests, outcries, Furies
The Abchvillain in the annals of the New York Yacht Club is not Ashbury, but an English peer who came along 22 years later to contest for the cup. He was Lord Dunraven, twice a challenger with his two Valkyries and famed in yachting history for accusations of fraud and deceit as shrill as any war cries uttered by the Teutonic Furies after which his yachts were named.

When he first challenged, Dunraven was in his early 50s. He was a soldierly, energetic man with a large nose and a ruddy face. He had given up violin playing for yachting following his graduation from Oxford: "The violin," he said in explanation, "requires suppleness and delicacy of the hands and fingers; handling ropes, rowing, etc., are incompatible with that necessary condition." His first challenge in no way forecast the unpleasantness that was to come. He lost in three straight races, all close but without incident. He was a popular loser. He had tried hard—even to the extent of attempting to improve the physical condition of his crew with a nonalcoholic health mixture of his own devising, a black-hued concoction referred to in the press as a Valkyrie cocktail. For his colorful though bizarre personality (he kept monkeys and an aviary of birds in his hotel suite), he was widely feted by New York hostesses; his style of dress (he wore pink shirts) and particularly his footwear were copied by a few of the more eccentric elegants of the day—a witness to the extent of his popularity since at the time Dunraven was suffering severely from gout and limped around New York in a brown shoe and a slipper.

The first inkling of the disastrous break in relations that subsequently developed was contained in a letter from Dunraven to the New York Yacht Club just before the start of the series between his second challenger Valkyrie III and the American boat Defender. It was a request that both challenger and defender be measured and marked at the waterline. Dunraven pointed out that it was possible to add ballast surreptitiously to increase the waterline length. Since it is axiomatic that the lengthier the hull in the water the faster a yacht is capable of moving, Dunraven was implying the possibility of deceit. It was a strangely worded request, and no one is quite sure what prompted Dunraven to make such an implication, except that possibly he had heard a rumor prevalent that year that tampering with water ballast had been alleged on a yacht owned by C. O. Iselin, the manager and a member of the Defender syndicate. In any case, the New York Yacht Club dutifully appointed a committee, and the day before the first race measurements were taken.

Late that same night, Valkyrie's crew noticed some strange activity aboard Defender. They reported to Dunraven that the tender Hattie Palmer was lying alongside Defender and that, amid the sound of hammering and clink of iron, the crews were seen carrying bulky weights from one boat to the other.

Naturally, Dunraven took a good look at Defender the next morning, and she seemed to him to be three or four inches lower in the water. Following his defeat in the first race, he called for another measurement—which was found to be an eighth of an inch off the original, such an insignificant figure that the New York Yacht Club considered the matter closed.

Dunraven made no further mention of ballast during the series, which was unfortunately marred by other incidents and protests, but on his return to England he made public his charge that ballast had been added to Defender before the first race. The reaction of the New York Yacht Club was immediate. C. Oliver Iselin called for a full investigation. "I stand before the world," he wrote, "solemnly charged with an offense as base as could possibly be imputed to a sportsman and a gentleman." A hearing was called, and Dunraven recrossed the ocean to personally repeat his charges. He failed to prove them. The testimony disclosed that the suspicious activity aboard Hattie Palmer was simply cutting in half lead pigs momentarily removed from the narrow bilge of Defender in order to stow them farther down and thus increase her stability. Public feeling turned completely against Dunraven when he persisted in his charges; he finally became the subject of a pun repeated ad nauseam ("has he done ravin' yet?") and left the country a thoroughly disliked figure...casting a pall upon America's Cup racing that only the benevolent figure of Sir Thomas Lipton, 3 years later, could dispel.

A misanthropic wizard
To his few acquaintances Nathaniel Herreshoff was known as Captain, or "Mister," Nat, but to the outer world he was famous as "The Wizard of Bristol"—an accurate sobriquet which suggested not only the magic of his inventiveness as a designer and engineer, but also indicated something of the mystery of his personality. He was a gloomy, taciturn New Englander, who stalked around his yards in Bristol, R.I. with a walnut stick tucked under his arm; highly strung and irritable, a misanthrope of extraordinary secretiveness, whose sole satisfaction was in hard work to which he dedicated himself from 6 in the morning until 10 at night. The first boat he designed was the sloop Violet, whose performance so disappointed him that he smashed her model with an ax. In later life he designed five cup defenders, all successful. In 1937, nearly 90, bed-ridden, he was still absorbed enough in his life's passion to watch his yards recondition the J boats Ranger and Endeavor II. They were not long down the ways when he died.

The world's greatest loser
Of his five challengers—all named Shamrock and with a small potted shamrock below for luck—not one was able to lift "the ould mug," as Sir Thomas Lipton called the cup. Sympathy for him in his vain attempts was so widespread that following each defeat Sir Thomas would humbly accept a substitute trophy—a loving cup that the American public got in the habit of giving him—and he would vow to try again with a boat that "would make Americans sit up." By his fifth attempt, nationalism had gone by the boards and, when he cried out "I cannot win! I cannot win!" following his defeat in the 1930 series, there was, as Ring Lardner wrote, "hardly a dry eye in any American speakeasy." One sympathetic lady, short on nautical knowledge, wrote him that the Americans were putting something in the water to prevent his Shamrocks from winning. Yes, Lipton wrote back ruefully, yes, they were putting faster boats in the water.

He was a tall man, his face the familiar one that graced the tin boxes of his tea—the white mustache, the little tuft of hair on the underlip and the undersized yachting cap which he set at a jaunty angle and wore on all occasions. Once during an ocean voyage a lady passenger spotted the cap, mistook Lipton for a deck steward and tipped him a shilling when he was successful in producing a deck chair for her. "I took the shilling," Lipton reported of the incident, "and tipped my cap to her in the approved manner."

He came from humble beginnings, born in Glasgow, Scotland, the son of Irish parents who had fled their native country to escape starvation in the Black Year of 1846. At the age of 10, Lipton was hired as a messenger boy in a stationery shop, running his errands barefoot across the winter streets for four shillings (about 60¢) a week.

As a young man he left for America to seek his fortune. He returned with barely ¬£100 (about $500) in savings, along with a rocking chair and a bag of flour promised his mother who had professed a craving for American-style pancakes.

His Cinderella rise in fortune started on his return. He invested his savings in a small provision store, and utilizing present-day promotion and selling methods, parlayed it over the years into an immense chain. He was a pioneer in many aspects of business—the originator of hard-sell advertising. To proclaim the ham products in his provision stores, for instance, he marched battalions of pigs through the Glasgow streets, each with a cloth covering on his back with the lugubrious message for all to read: "Lipton's Orphans Bound for Lipton's."

At the turn of the century, famous and rich, Lipton received his baronetcy through the strong backing of the Prince of Wales, later Edward VII. The prince was a staunch friend; a great yachtsman himself, he interested Lipton in yachting and in the great challenge posed by the America's Cup.

Lipton's yachts did well with the marked exception of cup competition. He had so many trophies on display in the main dining salon of his steam yacht Erin that there was not enough room to serve meals. Yet Lipton can hardly be classed as a true yachtsman. He rarely went aboard his cup challengers. The only recorded instance of a visit to Shamrock IV when she was in America was in the company of a dress manufacturer and a flock of models for a publicity photograph. As for the races, he watched them from the deck of his Erin, leaving the management of the Shamrocks entirely to the designer and captain. His application to yachting was essentially romantic. "Ah," he said once during his last days in Newport waters, in his 80s then, frail, the jauntiness fading, "look at her lines—tell 'em anywhere—the lovely green lady," and no one quite had the heart to tell him that he was actually peering at the American defender Enterprise.

Following his last defeat, yet another loving cup was given him, this one on the suggestion of Will Rogers on behalf of Americans wishing to show their appreciation for his good sportsmanship. The cup stood two and a half feet high and was worth many times the monetary value of the America's Cup Sir Thomas had spent 21 years and an estimated $5 million trying to capture. The loving cup was presented in a tear-drenched ceremony in which Lipton broke down during his acceptance speech. One of the many symbols engraved on the cup was a spider and its web, with above it the word "perseverance."

A head-standing genius
He was an odd, multifaceted genius, whose designing brilliance he inherited from his father (designer of three America's Cup defenders in the 1880s) along with the family habit of somersaulting in exultation, or standing on his head—a position from which he often, and at considerable length, quoted from the poems of Algernon Charles Swinburne. He was a flamboyant dresser, sported a giant drooping mustache like Robert Louis Stevenson's, and arrived in the boatyards in a stripped-down Lancia, with a trained seal sitting up next to him in the front seat. While he worked, the seal sported in the harbor around the hulls of Burgess' remarkable creations: the great J boats. Into the lines of these yachts, more than 80 feet on the waterline, up to 135 feet over-all, with masts that towered as high as a 14-story building, went Burgess' modern theories of aircraft engineering and aerodynamics—a "mechanical invasion" decried by the traditionalists, but which culminated in the famous Ranger. The "ultimate conception" she was called, so fast her speed might be matched but never surpassed.

The great professional
Recurrent in Sir Thomas Lipton's troubled dreams of cup contests was the nightmare figure of Captain Charles Barr—a laconic Scotsman with a slight, calm voice who signaled his crews into action with spare hand motions—directing crews that numbered over 50 men, some of them stationed 100 feet forward of the steering post on the immense defenders, a few of them, the mastheaders, as much as 80 feet aloft. They were molded into teams of such remarkable efficiency that yachts captained by Charlie Barr were considered nearly unbeatable. He successfully defended the cup three times, and in 1905, in the schooner Atlantic set a record for transatlantic crossings for sailing vessels which still stands after 53 years—12 days, four hours, and one minute. Even his death was attributed to speed: a hidden reef, so the story goes, once stopped the onward rush of a yacht he was commanding so suddenly that Charlie Barr was slammed up against the spoked wheel and suffered internal injuries, which ultimately closed out the legendary career of the greatest and last of the professional skippers.

The great amateur
He was the first amateur skipper of a defender, as neat and tailored ashore as befits a director of 50 corporations, treasurer of Harvard College and Secretary of the Navy in Herbert Hoover's cabinet. But on the water Charles Francis Adams appeared in soiled and tattered duck trousers, a nondescript sweater and a battered canvas sailor's hat with the brim tugged down to his cheekbones. "The Deacon" they called him, because of his abstemious habits—he never drank a drop of liquor in his life—but his sulphurous deep-sea cussing was famous all along the New England coast. He sailed in any craft he could get into. The first time Lipton saw him, Adams was racing in a dinghy. At the starting gun he caught his mainsheet on a marker buoy and in a confused tangle revolved tightly around the buoy like a dog chasing his tail. Unhappily for Lipton, the error was no indication of Adams' ability. He sailed all yachts, regardless of size, with equal skill—slave of a passion for racing, and an indefatigable love of the sea so consuming that on occasion his friends would remark they were surprised he ever came ashore at all.

The grand old man
Although it was an inherent part of the drama and tradition of the America's Cup that the competing yachts were the largest ever to engage in a series of match races, most of the skippers commanding them were trained in the dories and dinghies of their youth. Harold S. Vanderbilt was one notable exception. Though he started in a 14-footer at the age of 11, afterward he raced almost exclusively in large boats. Bouncing around like a cork in a Snipe or a Comet, while it appealed to Charles Francis Adams, was not Vanderbilt's idea of sailing. He missed the feel of the sense of power present in large boats. In 1937, in a widely publicized event, Vanderbilt and four other J boat skippers stepped gingerly into little Brutal Beast 12-footers to compete for a trophy donated by Arthur Knapp Jr., then a member of Ranger's afterguard, one of the best small-boat sailors in the country and today skipper of the 12-meter Weatherly. The two races sailed were both won by T.O.M. Sopwith, the English challenger who was never that summer to have the satisfaction of leading Vanderbilt across the finish line in a J boat. In both events Vanderbilt finished last.

Victory in these small craft did not come easily to a yachtsman who only three years out of college won the 1910 race to Bermuda in a 53-foot Herreshoff schooner, Vagrant, and in 1913 while still in his 20s was sailing another Vagrant—which was 80 feet on the waterline. In such yachts Vanderbilt was almost unbeatable. Generally recognized as the finest large-boat skipper who has ever lived, he is in many ways a composite of the outstanding men who preceded him in the history of the America's Cup.

As a skipper he equaled Charlie Barr's record of three successful defenses of the cup and, aboard the defenders Enterprise (1930), Rainbow (1934) and Ranger (1937), he commanded his crews with the same firmness and brilliance, coupled with a voice of command that, though rarely interspersed with Charles Francis Adams' deep-sea oaths, could cut through a gale of wind. Much like Adams, Vanderbilt's competitive spirit was a consuming passion—in marked contrast to the professional skipper aboard Shamrock V, his first opponent, a man who admitted he raced solely to earn his salary from Sir Thomas Lipton, his true passion being neither the sea nor racing, but the standing of the soccer teams in Britain's Football Association.

By nature, Vanderbilt is shy, with as little liking for the tumult of public acclaim as Captain Nat Herreshoff; yet as a designer and experimenter he was a perfect partner to the bizarre extravert genius of Starling Burgess—appreciative of the technological developments that would make such J boats as Ranger invincible.

Last spring Vanderbilt, now in his early 70s, was honored at a testimonial dinner given him by the New York Yacht Club in its enormous Model Room, whose walls are almost hidden behind the wooden hull models of famous yachts—among them, of course, all those associated with the America's Cup. After the dinner Vanderbilt gave a lecture illustrated with slides showing the giant J boats in action. The last slide he showed was his favorite: the famous Morris Rosenfeld photograph of five J boats running before the wind in 1937—Ranger, Rainbow, Endeavor I, Endeavour II, Yankee. Vanderbilt's Ranger is far in the lead, flying the largest sail ever made, an 18,000-foot parachute spinnaker which bellied so far out over the bow that a temporary bowsprit was set up to catch it and keep it out from under the boat if it ever collapsed.

Vanderbilt remarked that it was unfortunate that these beautiful yachts "were sailing to a destiny which turned out to be the scrap heap." Not one of them exists today. A few spreaders and spars remain to decorate the walls of New England taverns. To build another would cost an astronomical sum, more than $1 million. But Vanderbilt has always believed that "size and importance are brothers," and up until last year he hoped the British would challenge with a J boat. He felt so strongly that any diminution in size of competing yachts would demean the historical value of the trophy that he might have financed, had the British so challenged, the construction of an American J class defender.

Now he has changed his mind. In his final remark to the members of the New York Yacht Club he indicated his delight that the America's Cup would once more be raced for by "smaller, but no less worthy contenders." This summer, as a member of the America's Cup committee that will select a defender, he has been watching the trials off Newport from the deck of his motor sailer Versatile. As the trials have progressed, he has become absorbed, until he now seems as involved in the cup defense as when he was at the wheel of Ranger. His motor sailer, flying the cup committee pennant, is immediately recognizable in the spectator fleet, not only for the way she dogs the heels of the 12-meter contenders so that Vanderbilt can keep a close eye on them, but also because he keeps her under sail—purportedly to steady the yacht in rough weather but more likely because he is at home with canvas aloft.

The crews of the contending yachts admit that with Vanderbilt's Versatile close aboard, hearing him bellow commands to keep her well clear of their wind, they are conscious of being scrutinized by a great skipper from another era, a living legend, but a man still considered the most perceptive yachtsman in the country. At Newport his presence is very much felt as the date approaches for the opening of a second century in the history of the fastest yachts in the world and the men who race them.


Eagle (-2)
Birdie (-1)
Bogey (+1)
Double Bogey (+2)