By John Rousmaniere, The New York Yacht Club: A History © John Rousmaniere

When Harold Vanderbilt in 1930 turned his considerable energy and talents to the America’s Cup, he chose longtime CCA member Charles Sherman Hoyt as his chief advisor. “I have never sailed with a more proficient yachtsman,” Vanderbilt wrote of him.

Always called Sherman in honor of his granduncle, General William Tecumseh Sherman, he was a master of any boat he sailed, wherever and whenever she sailed. He started out in small boats and often led the New York 30s and 6 Metres in local and international championship regattas. Shifting to the new sport of ocean racing in middle age, he did so well in the Fastnet Race — he was skipper or first mate in three winners between 1928 and 1935 — that someone cracked that the best way to win the race was to first shoot Sherman Hoyt.

Stories about him were legion. During the 1935 transatlantic race, the 70-foot wishbone-rigged ketch Vamarie was running fast before a small gale, her sails held out by preventers, when her professional captain, Alexander Troonin, fell off the bow. The boat ran him over and spat him out in her wake. Vamarie had no engine, but that did not bother Hoyt, who was steering. He put the helm hard down until the sails were aback and braking her to a halt. Gathering sternway, he brought her bow off, got her underway again, jibed, and with the spinnaker flailing and the main boom and spinnaker poles in pieces, brought the ketch head to wind alongside Troonin, who was back on deck less than ten minutes after going overboard. Hoyt’s lengthy small-boat experience had trained him in the art of getting a feel for the wind and the boat. Still, it takes another level of genius to pull off such a feat. Sailing and seamanship appeared to come naturally to him.

So did fond and confident relations with other people. In England he sometimes raced in the royal cutter Britannia with King George V and Queen Mary. He told a story about her that has been related by a friend who heard it often, Fred Hecklinger: “It seems he was alone in the main saloon, eating some lobster salad, at a time when Queen Mary was occupied rearranging her clothing in a nearby water closet. The boat rolled unexpectedly, and the royal personage became somewhat unbalanced while seated on her throne. And due to a faulty latch on the door, Her Majesty came tumbling out into the main saloon not altogether properly dressed.” Sherman rushed to her aid, but was unsure of what to say. Not the Queen: “Mr. Hoyt, I do believe that you are more embarrassed than I.” Hoyt finished the anecdote with the comment that this probably was the first time that a Queen of England had got down off her throne before an American.

Everybody loved him. “Sherman Hoyt the whole yachting world has heard of, and I will say no more than that it is all true,” wrote Sir Fisher Dilke, who had found Harold Vanderbilt such difficult company. “He is also the greatest fun to be with. A slight, trim figure with brilliant black eyes, a skin as tanned as any I have seen, and a vast peak to his hat all set off his gay clothes to the utmost.” An English yachting journalist who knew Hoyt well from his many visits to Cowes, John Scott Hughes, described him this way: “Sherman is a smallish chap (not the ‘little runt’ he sometimes describes himself), highly charged with some extra special essence of vitality.” Hughes compared Hoyt favorably with an American general he also knew, calling him “a pocket-sized, seagoing Eisenhower” showing the same “amiable belligerency, intense tip-toe alertness, and all pervading impression of power.”

 

Defending the Cup

When Vanderbilt and Hoyt first sailed Enterprise in 1930, it was Hoyt who had the most Cup experience. Ten years earlier he was in George Nichols’s afterguard in Vanitie when she lost the defender trials to Resolute. The club then named him its official representative as the observer in Shamrock IV. As he watched the British gain a two-race lead and then fall apart, Hoyt became convinced that such a boat required a skilled, all-commanding captain, not the traditional Cup dual command shared by a syndicate manager and the helmsman. “Naturally I expect such a man to delegate authority and many details to subordinate members of his organization,” he told W.P. Stephens, “but the helmsman should be supreme and be responsible for the general policy.”

Hoyt found such a man in Harold Vanderbilt. The yachting historian Ian Dear praised “Vanderbilt’s flair for molding a team regardless of his own personality.” A team, and also a boat: Enterprise was 1930’s most innovative J. With winches and half her crew below deck, she seemed to sail herself and was dubbed “the mechanical boat,” suggesting that the skipper was “the mechanical sailor.” Some people wondered, in fact, if Vanderbilt had feelings. Your author’s father, Jim Rousmaniere, told about sailing in Vanderbilt’s Vim on the N.Y.Y.C. Cruise in 1940. One day the other 12 misread the circular and was just getting sails up when the starting gun fired, yet Vim kept racing. “The crew became uneasy. I looked at Rod Stephens and he looked at me, and he went aft and said, ‘Mike, we can’t do this.’ Rod told him Vim should go back and ask for a restart so there would be a real race.” Vanderbilt, said my father, showed not the slightest understanding of what Stephens was talking about. He eventually was persuaded, Vim sailed back to the committee boat, the race was restarted, and Vim won.

Yet Vanderbilt did occasionally reveal a touch of vulnerability. In his book about the 1930 Cup, Enterprise, he acknowledged that he came into the match knowing that most Americans wanted him to lose the America’s Cup. He understood. “None desired to lose it permanently, but merely temporarily to relinquish its possession, perhaps partly because they felt that we had held it long enough, but largely because of their love, their sympathy, their admiration for that grand old sportsman, Sir Thomas Lipton, who had spent so many years and so many millions in a futile quest.” He admitted to sharing those feelings. Vanderbilt was a boy when he first met Lipton, at Newport in 1899. Now, thirty-one years later, his Enterprise thoroughly dominated Shamrock V. Well ahead and nearing the finish of the last race, Vanderbilt handed the wheel off and went below to write in the log: “And Shamrock V, where is she? We look astern. She is about a mile behind, a badly beaten boat; not only in this race but in all the others, except possibly the first. 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?”

Another vulnerability of Vanderbilt’s was his sailing ability in certain conditions — and again he admitted it. Mostly he was confident. Frank Snyder, a future N.Y.Y.C. commodore, learned that much during his first exposure to the America’s Cup in 1937. In an oral history interview with Peggy Lord in 1999, he told how his family’s powerboat came into Newport after one of the races. “We rounded Fort Adams and came into Brenton Cove, right off of Harbour Court but very close to it, and we watched Ranger come in under sail. She sailed down before the wind almost to Newport’s docks and then Commodore Vanderbilt put the helm down and swung the bow into the wind. It looked to me like she went for ten or fifteen minutes before she stopped. And he shot the mooring as if Ranger was a little 16-foot boat, and—I tell you honestly—the bow of Ranger stopped right over the buoy. I have never seen that exhibition of sailing.”

Yet when steering upwind in light air, Vanderbilt was uncomfortable and, he was sure, ineffective. There was no weather helm and his preferred stance at the wheel, standing behind the binnacle with a mate down to leeward calling the jib, made him unresponsive to wind shifts. He discovered that Sherman Hoyt, the natural sailor, steered extremely well in these conditions, kneeling on the side deck with one hand on a spoke so he could see the jib. Whenever the wind became light enough to set one of the big, full genoa jibs of that time, Vanderbilt always passed the wheel to Hoyt. This was just one rule in Vanderbilt’s disciplined system of racing a sailboat. Hungry for information and advice, he organized his afterguards into committees who advised the designated tactician. His tactician in 1937 in Ranger, Olin Stephens, told how he and the other members of the afterguard “conferred continuously, away from the skipper, so that I would be ready without a second’s delay to answer Mike’s tactical questions, such as, ‘Should we tack or keep going?’, ‘Hold high or drive?’”

In assigning so much authority to others, Vanderbilt may have been compensating for another weakness of his own, which was a tendency toward indecisiveness when he was not leading the race. After watching Vanderbilt for many years from his position on the Race Committee boat, Gherardi Davis observed in 1928 that while Vanderbilt could do little wrong when leading, when behind he could waver. Davis put it this way: “Vanderbilt sometimes stutters.” He added, “I think he knows this.”

Holding their Breath

Vanderbilt and Hoyt came into the 1934 Cup match in Rainbow after almost losing the defender trials. Their opponent was the very fast Endeavour, with a skipper of considerable resourcefulness, T.O.M. Sopwith. These were very different men. Fisher Dilke, who sailed with both Vanderbilt and Sopwith, compared them this way: “The American, cold, efficient, scientific, most accurate, and subordinating everything, including himself, to the overpowering desire to produce as fast a boat as he could within the rule. The other of a warmer temperament, more impetuous, and allowing his natural vivacity fuller play. No less scientific or efficient but, though carrying an afterguard with talents as great as those on Ranger, centralizing action a good deal more in himself than did Vanderbilt.” To put it another way, the American was the CEO, the Englishman Sir Galahad. Because the first was the typical N.Y.Y.C. defender, and the second the typical challenger, the story of the 1934 America’s Cup match summarizes in a nutshell how it was that the New York Yacht Club held onto the America’s Cup for 132 years.

Harold Vanderbilt was an extremely unhappy man on the afternoon of September 20

Harold Vanderbilt was an extremely unhappy man on the afternoon of September 20, 1934. In what he would call “the low point in my sailing career,” halfway through the third race against Endeavour, Rainbow trailed in the four-out-of-seven series by two races and in this race by six-and-a-half minutes. In light air under genoa jib on starboard tack, Rainbow inched toward the finish line 15 miles away with the challenger sailing, as Vanderbilt recalled, “right ahead, looking very small indeed.” Gazing at Endeavour’s counter was like looking into the maw of failure not just for him but for the club. The system ruled, and Vanderbilt handed the helm to Sherman Hoyt and went below. He would recall that bleak moment this way: “As far as I was concerned, the America’s Cup was on its way back to England. Three down and one to go against a faster boat was a little too much.” Over coffee and sandwiches, Vanderbilt struggled to rationalize losing the America’s Cup while the Royal Yacht Squadron’s observer, Sir Ralph Gore, politely murmured sympathies that surely were barely half-felt. In the end he decided that no matter how good a change of hands might be for yachting, he surely did not want to be remembered as the man who allowed it to happen.

On deck Sherman Hoyt was calmly weaving some wizardry to make this race, as he would say in his autobiography, “one of the most astounding ones of my experience.” In an all but total silence, broken only by whispers by his navigator, Zenas Bliss, and the occasional clink of a winch, Hoyt sat on deck, his eyes focused on the jib luff and his outstretched right hand lying gently on a spoke of the wheel. Keeping up a precise dead reckoning plot, Bliss told Hoyt that the wind had faired enough to convert the original beat to the finish almost into a close reach.

Although he was easily fetching the finish line, Hoyt headed up until he was almost closehauled. Exactly why he did that has long been a subject of dispute among America’s Cup fanatics. Hoyt later said he saw a bit more breeze to windward, while Vanderbilt believed he was compensating for leeway. But Hoyt’s thoughts were as much on Sopwith as they were on wind. Hoyt was a master of competitive psychology. “I am certain,” he later wrote in his memoirs, “that any who have achieved success as racing helmsmen have always made a careful study of their opponents and, insofar as possible, have taken advantage of any perceived weaknesses.” He had learned a great deal about Sopwith during his summers of racing in England. One of Sopwith’s weaknesses was an obsession with covering the competition. Another was his not entirely respectful and trusting relationship with his crew, and especially his navigator. When the professional crews of both boats disputed their pay over the winter, Vanderbilt negotiated a settlement with his well-trained team of Scandinavians. Sopwith, however, refused to make an accommodation with the twenty-six Essex fishermen who asked for compensation for their lost opportunities in the Channel while sailing Endeavour home in the fall. As a consequence, this demanding 130-foot racing yacht, with her 7,500 square feet of sail and wire sheets, was handled by a pickup crew of amateurs and professionals.

An unreliable crew was bad enough. Then there was the question of the navigators

An unreliable crew was bad enough. Then there was the question of the navigators. Zenas Bliss was a university mathematics professor and experienced racing sailor who had been hand-picked for the job by Sherman Hoyt. Over on Endeavour was a merchant navy officer, Captain William Paul, who had got the yacht across the Atlantic capably enough but knew nothing about tactical navigation (reportedly, he was unable to predict the apparent wind direction on the other tack). Even if Paul knew his job, as a professional seaman in a class-bound culture with a commander who lived by a chivalric code, he was not in a position to be taken seriously by Sopwith.

So it was that three miles into the last leg of race three of the 1934 America’s Cup, Sopwith—still many minutes in the lead, still able to fetch the finish line if he headed up just a few degrees, but not trusting his navigator—decided on his own to come about onto port tack and sail over to cover Rainbow. Once the 140-ton Endeavour settled down on her new heading, which was a few degrees away from the finish, it took her many minutes to get back up to speed as her bow inched toward her opponent. “No one moved on board Rainbow, no one spoke, everyone was lying flat on deck along the lee rail,” Vanderbilt would write of this moment in his book On the Wind’s Highway. “The sea was quiet; the little ripples running along the side were quiet; the rig, the sails, the ship, the wind—all were quiet. Conditions were ideal for relaxation, yet everyone was tense, for everyone knew that a vital moment was at hand. Where would Endeavour tack? That was the burning question! Would she tack to leeward of us, ahead of us, or on our wind? I hoped she would try the latter.”

And that was exactly what Sopwith did. Very likely, as the boats neared each other, Hoyt reached into his voluminous bag of tricks and pulled out one of the oldest of them all—heading off a few degrees without easing sheets to suggest that he was sailing below the layline and, therefore, persuade the other boat to carry on. It worked. Endeavour crossed Rainbow’s bow and kept on going. When she eventually tacked to starboard to cover, Hoyt came back up and, within a few minutes, put Endeavour into his backwind. The challenger tacked again.

“How does the finish bear?” Hoyt asked.

“A point to leeward,” Bliss replied. Hoyt cracked off for the line.

Rainbow gained ten minutes on that second leg, never once coming about, while Endeavour tacked four times and lost ten minutes. “Rainbow’s Victory a Maritime Miracle,” shouted a newspaper headline the next day. The yachting journalist Alfred F. Loomis chose a different metaphor: Endeavour, he wrote in Yachting, had given the race to Rainbow “wrapped up in cellophane and handed to her on a silver platter with Sopwith’s compliments.” That platter was presented by Sherman Hoyt.