This weekend, for the first time since Irish-Scottish tea baron Thomas Lipton lost the 1920 race to a New York Yacht Club syndicate led by railroad tycoon and art collector Henry Walters, the city will play host to the world's most famous boat race when the Louis Vuitton America's Cup World Series sails into town.
Instead of elegant yachts, the six teams competing in the Louis Vuitton World Cup series ahead of next year's America's Cup in Bermuda
will face off in carbon-fiber catamarans that look like jet airplanes, capable of going up to 40 miles per hour.
The boats may have changed beyond recognition but one thing has remained the same in the 165-year history of the America's Cup -- its allure for the world's wealthiest people and power brokers.
"The people who are attracted to the America's Cup are the people who are attracted to competition at any level, at any time," America's Cup historian and sailing author John Rousmaniere said in a phone interview from New York. "And Sir Thomas Lipton was at the top of the heap."
The current Cup holder is U.S. billionaire Larry Ellison, co-founder of software giant Oracle. He'll be up against five challengers including Olympic sailing legend Ben Ainslie, who next year hopes to be Britain's first victor since sailing's premier event began in 1851.
Lipton, a self-made man who was born into poverty in Glasgow, was the most persistent challenger in the America's Cup, plowing millions of dollars into five campaigns between 1899 and 1930 through the Royal Ulster Yacht Club. But all of his Shamrock boats were defeated, endearing him to the American public as a "folk hero" and "lovable loser" according to the event website.
Lipton wasn't the only illustrious name involved in the America's Cup at the turn of the last century. U.S. financier John Pierpont Morgan co-owned the 1899 and 1901 Cup winner Columbia, while the Vanderbilt family, whose wealth came from railroads and shipping, helped fund three Cup winners between 1895 and 1937.
The closest Lipton came to winning was in 1920, when Shamrock IV took the first two races before Resolute won the next three to retain the trophy for the New York Yacht Club.
That series was highly anticipated across North America, with New York hotels having to turn people away because they were at full capacity, while special trains brought in spectators from Canada, the New York Times reported on July 15, 1920.
"Resolute Wins Final Race By 19 Minutes 45 Seconds; America's Cup Stays Here," headlined the Richmond Times-Dispatch on July 28, 1920.
Lipton's relentless pursuit of success helped put the event on the map in the U.S., Bob Fisher, a sailing historian and author of numerous books on the sport, said by phone from Lymington on the English south coast.
"He was much loved by America and the Americans," Fisher said. "He was persistent, he wanted to win the Cup and spent a lot of money doing so."
Lipton may have spent as much as $2 million on his two challenges in 1920 and 1930, Rousmaniere estimated. That's roughly $27 million in today's money
Born in 1848, Thomas Johnstone Lipton became interested in the sport when he persuaded his parents to let him sail to New York from Scotland when he was just 14 years old, according to the America's Cup Hall of Fame website.
While in the U.S., he learned about the grocery trade and the power of advertising. Lipton returned home to his parents in Scotland five years later.
By 1914, he'd expanded the family's grocery shop into 500 stores -- laying the foundation for the nation's first supermarket chain.
He also created the Lipton tea brand, which is still in existence today.
Although Lipton never won the Cup and wasn't much a sailor himself, his highly-publicized attempts boosted his business in the U.S. as it helped promote his tea, Fisher said.
The 1920 race was the 13th edition of the America's Cup, and the first since 1903 after the outbreak of World War I prevented the race from taking place in 1914.
After New York Harbor became too busy with commercial shipping, the 14th edition moved to Newport, Rhode Island in 1930. It stayed there until 1983 when Alan Bond's Australia II beat Liberty to end the NYYC's 132-year dominance, the longest in sports.
During the 1920 races, New York Harbor was so filthy with oil and coal that the yachts had to be hauled out every two days to be cleaned, Rousmaniere said.
"The only person who wanted to have it in New York was Sir Thomas Lipton," Rousmaniere said. "All the people from his club and the New York Yacht Club wanted to have it in Newport where there was better wind, cleaner water and better sailing. But Lipton had a lot of followers and friends in New York and he made the decision. Most people would say it was the wrong decision because the wind was very poor for his boat."
Lipton didn't fare much better in his final attempt a decade later in Newport, where Shamrock IV was beaten by Enterprise -- skippered by Harold "Mike" Vanderbilt.
Lipton's reward after the final race: a specially designed cup for "the best of all losers."
Vanderbilt, who was a schoolboy when Lipton launched the first of his five challenges in 1899, preferred sailing over the family railroad business. A triple America's Cup-winning skipper, he helped develop the yacht racing rules, according to the America's Cup Hall of Fame website.
Vanderbilt summed up the feelings of the American public after the final 1930 race.
"Uppermost in our minds is a feeling of sympathy for that grand old sportsman, Sir Thomas Lipton, with whom our relations have been so pleasant," he said.
Although this was "perhaps his last attempt to lift the America's Cup," Vanderbilt said, "it has been our duty to shut the door in his face. In defeat lies the test of true sportsmanship, and he has proved to be a wonderful sportsman, quite the finest it has ever been our good fortune to race against."