One of sailing's most famous events, the America's Cup, is under way in Auckland this week. Mike Wilson remembers one of the world's first great entrepreneurial self-publicists, Sir Thomas Lipton, who competed in the race five times, and every time in a yacht named Shamrock.

As Auckland hosts the 33rd America's Cup, defenders team New Zealand and challengers Alinghi have spent an estimated $100 million to get their hands on what is quaintly called The 100 Guineas Cup. The race start last Saturday coincided with Nirvana Day, the Buddhist celebration of spiritual enlightenment and bliss.

For Sir Thomas Lipton, the Scots-born grocery and tea magnate who flew the flag of the Royal Ulster Yacht Club, spiritual enlightenment there may have been - but his five unsuccessful attempts to win the coveted trophy brought him anything but bliss.

Five times between 1899 and 1930, including a break of 17 years because of the build-up to and occurrence of the first World War, Tommy Lipton challenged for the America's Cup, and five times he lost.

As an octogenarian, he was planning his sixth assault on sailing's Nirvana when he died. Unmarried with no children, born of penniless parents from Shannock Mills near Clones in Co Monaghan and one of the richest men of his era, he was to die having failed to fulfil what many consider to have been his wildest dream.

Thomas Johnstone Lipton was born on May 10th, 1850 at 10 Crown Street in the heart of Glasgow's infamous Gorbals, the only surviving child of Irish parents who had crossed the Irish Sea in search of better fortune in Glasgow. They managed to carve out a reasonable, if not affluent existence for themselves by the time their son Tommy was born. His elder siblings John and Margaret were to die in infancy; another two siblings died during childbirth.

Having left school at just 10, against the better wishes of his parents Tommy Lipton was crossing the Atlantic steerage class by the age of 15, travelling from Glasgow's Broomielaw. He arrived in New York with just 30 shillings, his savings from working as a steward on the Burns Line Glasgow to Belfast ferry crossing.

At first, he eschewed the more traditional haunts for Scots/Irish emigrés, such as New York, Boston, Philadelphia and Baltimore, working on tobacco and rice plantations in Virginia and Georgia.

Lipton's final months of this first of many trips to the US were spent working as a grocery assistant in a New York store, and this was to ignite the young man's passion for shopkeeping and his panache for the entrepreneurial life.

He was unashamedly chameleon-like throughout his life, a skill he developed in the Irish areas of New York, where he would frequently play the Celtic card. He was quoted as saying, "When there is any argument as to my real nationality, I come right into the open with the declaration that I am a Scottish-Irishman or an Irish Scotsman, according to the leanings of the company I happen to be in at the moment".

On his 21st birthday, Lipton was to open the first of what would ultimately amount to 300 stores UK-wide, in Stobcross Street in Glasgow's Clydeside. His flair for marketing techniques was apparent from the outset. One of his early stunts, The Lipton Orphans, involved hiring a "stage" Irishman, a lookalike from the Victorian stage plays The Shaughraun or The Colleen Bawn, to lead two fat pigs through the streets of Glasgow.

With more and more outlets, he was stocking almost exclusively Irish produce, mostly from Westport in Co Mayo, procuring some 6,000 hams, 16 tons of best Irish bacon, 16,000 dozen eggs and 10 tons of butter each week from across the Irish Sea.

Lipton's horizons quickly widened, and he moved his headquarters to London, where his priority became the tea trade for which he today remains best remembered.

He also combined his flair for marketing with a streak of benevolence by offering £100 to the poor of Ireland if any three experts could tell the difference between the well-known and more reputable varieties and his new-to-the-market Lipton's blends. There is no record of how many hundreds of pounds were actually paid out to Ireland's poor.

He was, by the turn of the century, a very wealthy man, socialising in the highest echelons of society on both sides of the Atlantic, and knighted by Queen Victoria for effectively bailing out her faltering Diamond Jubilee celebrations with a cheque for £25,000.

There were also reports of a romance with the young Rose Fitzgerald, who would go on to marry Joseph Kennedy and give birth to President John F. Kennedy as part of the US "First Family". He had, by this time, thrown down the challenge to the American defender Columbia for the 1899 America's Cup, although attempts to sail under the traditional flag of the Cowes-based Royal Yacht Squadron were derailed when he was effectively black-balled and discredited by virtue of not being a "gentleman".

Lipton turned instead to the Bangor-based Royal Ulster Yacht Club, playing once more the "Irish card" and, according to Tommy Ross, the 97-year-old, recently retired historian of the club, this was little more than a flag of convenience.

"When he would come to the club for regattas, he would rarely come ashore," he said. "He had his luxury steam yacht Erin moored offshore and would use that as his base for entertaining and watching." Ross also recalls, "The story goes that he did not know his port from his starboard, or too much else about sailing for that matter; and on one occasion even failed to recognise his own Shamrock yacht. Mind you, he had his good points - his word was his bond - but it is sad that he left nothing to the club that had facilitated him for more than 30 years. Not even a cup to commemorate his membership."

Lipton's America's Cup record is not good: sailed five, won nil, lost five. But it was on Shamrock IV, following three successive 0-3 whitewashes by the American defenders, Columbia (twice) and Resolute that he was to come closest to fulfilling his dream.

In 1920, Lipton again threw down the challenge to Resolute, went 2-0 up in the five race series. Needing just one more victory to claim the famous 100 Guineas Cup, he nevertheless lost the last three races, going down again to Resolute, before losing for a fifth and final time - to Enterprise by 0-4 in 1930.

Sir Thomas Lipton had by that time turned 80 and was planning a sixth assault on the America's Cup when he died at home in London on October 2nd, 1931, leaving an estate estimated £1 million, of which £100,000 was donated to assist the poor women and children of Glasgow.

Scottish journalist and author Bob Crampsey, who wrote the book The King's Grocer about the life and times of Sir Thomas Lipton, says, "I think Lipton was fiercely proud of his Celtic roots, and, having been accustomed to such prolific success in business, found it hard to come to terms with becoming a serial loser in the America's Cup." Lipton was, however, presented with a cup specially commissioned by the Yacht Club of New York, in recognition of his being such a gracious loser. The Loving Cup, was the result of a nationwide appeal in the US that precluded anyone from donating more than $1 each - and donors included ex-presidents, captains of industry and socialites.

On presenting Lipton with the Loving Cup in New York in 1930, the mayor, James J. Walker, described him as, "possibly the world's worst yacht builder but absolutely the world's most cheerful loser". Seventy-three years on from Lipton's death, little has changed with the America's Cup he so coveted. Still, indecently wealthy men are throwing increasingly indecent sums in pursuit of a dream - a dream Lipton, characterised by the curator of the Sir Thomas Lipton Collection in Glasgow as "the prototype of Richard Branson", failed five times to realise.