There were a further six challenges before the turn of the Century, including the first of what came to be called the Lipton era of the America’s Cup. Sir Thomas Lipton, the Irish/Scottish tea baron challenged five times between 1899 and 1930. He became the loveable loser; a man whose good-natured approach to the obstacles stacked against him turned him into a folk hero and promoted his business interests in America as well.
While Lipton didn’t win the America’s Cup, he became one of the first to introduce the idea of sports sponsorship, and he realised a financial windfall from it. Lipton’s final challenge in 1930 was the first in the new J-Class boats. This was a period of magnificent beauty afloat, as the towering masts carrying an improbable amount of sail powered through the chop off Newport, Rhode Island. Harold Vanderbilt was selected to defend for the New York Yacht Club that year and did so with ease.