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 Fleetwing—that were about to depart on a wild adventure, an act that anyone in their right mind would have considered pure stupidity.
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 history—though 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 town’s 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.
“There was just pure arrogance,” Sam Jefferson, author of Gordon Bennett and the First Yacht Race Across the Atlantic, tells The Daily Beast. “It was just, ‘We're gonna do this race now because we’re rich and that’s what we do.’ You wouldn’t do a yacht race now in December. Even with all the weather forecasting…you still wouldn't do it now. And so, back then, it was very foolish.”
It all began one night in October, two months before the starting gun fired. James Gordon Bennett, Jr., the son of the legendary New York Herald owner; Pierre Lorillard, a tobacco dealer; and George Osgood, who was involved in finance, went out for a night on the town. They ended up at the exclusive Union Club, where they got deep into their cups.
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.
Bennett was the chief instigator in the transatlantic bet that night. The 25-year-old would eventually inherit his dad’s 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 son’s 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 Churchill’s 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.
“Spurred on by Jerome, aggravated by drink and awash with testosterone and braggadocio, three men who weren’t accustomed to losing anything bellowed and roared at each other until the only logical thing to do seemed to be to follow Jerome’s 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.”
Each of the contenders agreed to contribute $30,000 to a winner-takes-all $90,000 pot. Their boats would set sail in December.
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 captain—Bennett’s was the hardboiled Samuel Samuels who was straight out of central casting for a 19th-century man of the sea—the 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.
Papa Bennett may have thought his son’s 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.
This event was unlike any that had come before, and both countries eagerly followed the race, though news of the boats’ progress went dark as soon as they left shore. In a letter dated December 13, 1866, Henry Wadsworth Longfellow wrote: “I suppose you have seen something in some paper about a yacht race to England. I enclose you a paragraph about it. Pretty cold work, I should say.”
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.
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 that’s 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.
The race may have been foolhardy, but “it blazed the trail to say, this is a valid thing to do,” Jefferson says, though history has not rethought the stupidity of its December timing. It also provided a step in mending the relationship between the two countries, which had suffered after England quietly lent support to the Confederacy during the Civil War.
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 right—the 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.