D'Antonio's 'Cup' runneth over on Thomas Lipton

It's a truth almost universally acknowledged: rich, powerful men like to race sailing boats. Think of Ted Turner at the helm of the Courageous in the '70s, and, more recently, Oracle billionaire Larry Ellison, who spent millions wresting the America's Cup back from the Swiss. Before them both was Sir Thomas Lipton, founder of the eponymous tea company, who rose from the gritty streets of Victorian Glasgow to build a vast commercial empire.

A cheerful eccentric and master of publicity, Lipton is the subject of Michael D'Antonio's entertaining new biography, "A Full Cup: Sir Thomas Lipton's Extraordinary Life and His Quest for the America's Cup" (Riverhead, $26.95). Lipton made headlines wherever he went, and his participation in the 1899 America's Cup turned the event into a grand spectacle (though he lost). In a recent phone conversation, D'Antonio - a Miller Place resident, sailing aficionado and former Newsday staffer - talked about the man who Will Rogers said "made losing worthwhile."

Could we say that Lipton was the first celebrity tycoon?

He was the first playful celebrity tycoon. Prior to Lipton, men like Rockefeller, Morgan and Vanderbilt were celebrity tycoons of a sort. But these were men that broke strikes and developed monopolies; they were viewed with as much resentment as admiration. Lipton's role model was P.T. Barnum, not Ebenezer Scrooge. He thought that consumers could be reached through quality, fairness and fun. A jolly, somewhat doughty millionaire eccentric from the British Isles, he was happy to play a character.

Lipton himself couldn't sail, so why was he so consumed with winning the America's Cup?

Well, first of all it was the most visible sporting event in the world. Whenever something big was happening, you could always count on him to be there. He was also a child of terrible poverty who wanted to prove himself against the elite in a pursuit dominated by rich men of the sort he didn't quite match. His ambition to win was actually very American, as was his belief that a person with his origins could compete in sport of millionaires and, quite literally, kings.

Today's America's Cup boats are almost as advanced as the space shuttle, but weren't the racing vessels of Lipton's time also marvels of technology?

Yes, they were both works of art and the height of engineering. A lot of metallurgy developed around boats. Sort of like aeronautics today, the drive for stronger, lighter materials in yachting produced metals useful in other industries.

Between 1899 and 1930, Lipton lost five America's Cup attempts, yet he did so with grace, charm and humility. Where did his fortitude come from?

He considered the project of his life a magnificent victory, so losing a yacht race every five to 10 years, while painful, wasn't crushing. Everything was part of a whole creation, and that creation was himself. He is still associated with the America's Cup, and sailors still talk about him today.