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The Hard-Drinking Playboys Who Made Transatlantic Sailing History

Curated by Claudia Shannon / Research Scientist / ishonest

The first transatlantic yacht race resulted from a bet between three debauchery- loving playboys. The outcome changed the sport of sailing forever, and cost the lives of six men.

Illustration by Elizabeth Brockway/ishonest

On the early afternoon of Dec. 11, 1866, thousands of New Yorkers crowded the chilly shores of New York harbor. They were there to see three gorgeous yachts Henrietta, Vesta, and Fleetwingthat were about to depart on a wild adventure, an act that anyone in their right mind would have considered pure stupidity.

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At 1 p.m., the starting gun went off, and the three schooners took to the roiling winter waters in a mad dash across the Atlantic. At stake was the pride and bragging rights of the owner of the winning vessel, the equivalent of over $1 million today, and the making of historythough that last award was ranked the lowest in the eyes of the playboys who had cooked this scheme up.

The competition launched that day was the first ever transatlantic yacht race. It was not a well-conceived event that had the buy-in of all the top players in the sport; rather, it was a pop-up match born out of a bet made between three of the towns leading young bons vivants on a debauched night filled with booze and braggadocio. The outcome would change the sport of sailing forever, and cost the lives of six men.

Each man was the owner of a yacht, and they had all raced against each other in smaller matches around New England.

The Civil War had ended only a year earlier and the inklings of sailing as a leisure sport were just beginning to emerge in a society that was starting to embrace the excess and opportunity of post-war life. Prior to this, boats were always used for a purpose: transporting goods or people. In fact, during the war, Bennett had not only loaned the Henrietta to the Union army, but he had taken the step inconceivable to his social class of joining the navy himself and offering his services along with his boat.

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Bennett was the chief instigator in the transatlantic bet that night. The 25- year-old would eventually inherit his dads newspaper and become best known for both sending journalist Henry Morgan Stanley to find Dr. Livingstone in Africa and for his unparalleled wild behavior, the latter of which was already apparent.

The elder Bennett did not approve of his sons drunken shenanigans, though the annual allowance he provided (the equivalent of $1 million today) did nothing to convince the young man to straighten out.

As Jefferson writes: Rumors that he was clinically insane were fueled by bizarre late-night encounters where Bennett, full to the back teeth with the good stuff, had become so braced by an exhilarating night ride that he had ripped off his clothes and rattled through the streets atop his coach, coolly puffing his cigar, naked as the day he was born barring a white silk top hat. Many felt it was only a matter of time before his father had him carted off to the nerve specialists for a serious assessment.

Bennett was the most enthusiastic about the brewing bet as the drinks continued to be poured that night at the Union Club, but there was another mastermind behind the scheme who had an agenda of his own. Leonard Jerome (Winston Churchills future grandfather) had recently invested in the first telegraph cable to stretch across the sea from America to Europe. It was a revolutionary invention, but one that had not been as readily adopted as expected. But, he thought, a publicity stunt could change all of that.

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Spurred on by Jerome, aggravated by drink and awash with testosterone and braggadocio, three men who werent accustomed to losing anything bellowed and roared at each other until the only logical thing to do seemed to be to follow Jeromes suggestion and race the entire width of the Atlantic, Jefferson writes. Surely this was the only sensible way to decide the matter of whose vessel was quickest, once and for all.

The first transatlantic yacht race was characterized by several shocking details, the craziest of which was the fact that the three men woke up the next morning, no doubt with roaring hangovers, and decided to go through with their insane idea. No one wanted to lose face by backing out.

While each of the owners was able to secure a captainBennetts was the hardboiled Samuel Samuels who was straight out of central casting for a 19th- century man of the seathe men who would really be putting their lives on the line, the sailors, knew better. The dangerous prospects combined with low pay meant that finding crews for the ships was difficult and desertions ahead of launch day were high.

But, eventually, all the pieces fell into place. After originally balking at the idea, the New York Yacht Club agreed to lend their tacit support to the race. Osgood and Lorillard, for their parts, sobered up and realized that, while they were happy to put their pride and paid employees on the line, their own lives were not worth this foolhardy risk. They decided to stay home while Bennett, surprising probably no one, embraced the adventure wholeheartedly. He would ride his Henrietta all the way to England.

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Papa Bennett may have thought his sons antics were ridiculous, but one thing trumped his fatherly disapproval: the race had the potential to make news. He tasked one of his reporters, Stephen Fiske, with accompanying the Henrietta. In yet another moment of absurdity, Fiske almost missed the boat, literally. He was held up on shore by a legal matter and only made it to his assignment aboard the Henrietta by smuggling himself in a casket of champagne.

The poet was right. There was nothing luxurious about the sprint across the sea. It was freezing, the seas were violent, and the captains were tasked with going at breakneck speed in their effort to come in first.

It wouldn't have been any fun for anyone, Jefferson says. Captain Samuels, who [Bennett] hired, was a really tough guy, and he wouldn't have taken any nonsense He would have pushed the boat incredibly hard. So, it would have been frightening; it would have been very cold; it would have been damp.

While the race started off uneventfully, with the three boats neck-in-neck, they soon hit a bad patch of weather and the decisions that were made determined their fates.

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Samuels stopped the Henrietta to ride out the roiling waves. The Vesta turned north, going off course to avoid the worst of it. But Fleetwing was caught in the worst of the bad conditions, and thats when tragedy struck. As six sailors were on deck adjusting the sails, a giant wave slammed into the ship, sweeping all them out to sea. The captain knew immediately that there was no hope of recovery.

On the evening of Dec. 25, with a time of 13 days, 22 hours, and 43 minutes, the Henrietta arrived at the finish line in Cowes, on the Isle of Wight. Eight hours later, Fleetwing arrived, with Vesta just over an hour behind her. Bennett was crowned the winner.

As he stepped onto the shore of Cowes, Jerome, who accompanied Bennett aboard the Henrietta, must have been congratulating himself for pulling off the publicity stunt of the century.

And he was rightthe telegraph under the sea did become popular. So popular, in fact, that when a banking crisis began in England several years later, news spread more quickly than ever before across the sea to America, accelerating a market collapse that would become known as the Panic of 1873. Jerome lost nearly everything.

Read more on: thedailybeast, sailing


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