Somewhere en route from his swanky hotel room to New York’s City Hall, Sir Thomas Lipton may have permitted himself a wry chuckle at the glorious irony of it all.

He was, after all, a Gorbals boy who hauled himself from the Glasgow slums to become one of the world’s greatest and wealthiest merchants.

A charming and resourceful entrepreneur, who broke the shackles of low birth to mingle with kings and captains of industry at the highest echelons of society.

He had built up a hugely profitable grocery business which would serve as a template for the modern supermarket and established a global tea brand bearing his name which survives to this day.

A retailing genius, his life appeared set upon an unerring trajectory of success. And yet, here he was on a chill December day in 1930, a jovial octogenarian passing sidewalks lined with well-wishers cheering him on his way to be honoured for three decades of abject failure.

For all that his business interests had made him as rich as Croesus, his untold millions were never enough to help him land the one treasure he came to prize above all others: the America’s Cup.

Yachting had been the grandest passion of Lipton’s life – one he shared with the future Edward VII – and he yearned to become the first Briton to hold aloft the sport’s most prestigious trophy. Five times his crew raced; five times they came up short.

In more than 30 years of trying, he once quipped, he never managed to ‘lift that auld mug – surely the most elusive piece of metal in all the world’. 

What he did win, however, was the hearts of the American public, a large number of whom appeared to be rooting for this indefatigable Scot rather than their fellow countrymen.

As his fifth and final attempt ended in defeat, a smiling Lipton shook the winners’ hands, said the best team won and insisted that the 30 years he spent chasing his dream had brought him some of the happiest hours of his life and ‘splendid friends’.

His perseverance and sportsmanship only endeared him further to his transatlantic hosts who felt that such good-natured pursuit of his great sporting ambition should not go unrecognised.

Hollywood and high society mobilised to launch a public appeal which led thousands of Americans, including future US president Franklin D Roosevelt, to donate funds for an alternative trophy.

The two-handled solid gold ‘loving cup’, designed by Tiffany’s, features a representation of the America’s Cup on an enamel shield depicting the red, white and blue of the American flag and bears the inscription ‘To the Gamest Loser in the World of Sport’.

On each side of the base, fashioned from 25kg of silver supplied by miners from Utah, are four symbols of Fraternity, Integrity, Courage and Perseverance.

The many letters sent in by contributors were turned into a bound volume presented to Lipton along with the spectacular trophy.

The mayor Jimmy Walker joked that Lipton was ‘possibly the world’s worst yacht builder but absolutely the world’s most cheerful loser’. Roosevelt, meanwhile, wrote: ‘Sir Thomas and his good sportsmanship are a lesson to every American.’

Lipton was so overcome by emotion he was unable to finish his speech and a friend had to step in to deliver his words of thanks.

Within a year, Sir Thomas Lipton was dead having bequeathed the bulk of his fortune ‘to benefit the poor of Glasgow’. His many sporting trophies were also donated to the city of his birth, including his precious Lipton Cup. 

Yet now, this uplifting tale has taken an unhappy turn after it emerged the Cup was stolen from its display case in Glasgow’s Riverside Museum in mysterious circumstances.

Last month, police revealed the theft had taken place overnight on October 22 last year and was only reported by cleaners the next day as there had been no signs of forced entry to the museum.

Detective Sergeant Bob Carrigan, of Police Scotland, said the crime was kept quiet at the time to minimise the risk of the 18-carat gold trophy, estimated to be worth around £500,000, being destroyed. He said the trophy was ‘of significant historic value’, adding: ‘Extensive inquiries remain ongoing and have included CCTV review and conventional inquiry, including within the art world.

‘I am now appealing to the public for their help as part of our investigation to find and return the item to the museum.’

Interpol has since been notified along with the Art Loss Register, which is meant to alert international art dealers (reputable ones anyway) to stolen goods and prevent any attempted sale. A £25,000 reward for information leading to the cup’s recovery has even been put up by a local radio station.

Yet, seven months later, no sightings of the Lipton Cup and no arrests have been made.

As time marches on, hopes fade for its recovery and a question arises: has a trophy struck to honour the world’s best loser itself now been lost for good? Jane Rowlands, the head of museums and collections at Glasgow Life, called the theft disgraceful.

She added: ‘This is not only a loss for the museum, but a theft from the people of Glasgow, whose shared heritage our collections represent.’

What this audacious theft has done is cast a light back onto the rather extraordinary life of one of Scotland’s most controversial tycoons, whose exuberant public persona hid a conflicted private life – some of which may have raised more than an eyebrow among his adoring American fans.

A shameless self-publicist, who placed himself and his name at the heart of his business empire, Lipton cultivated his image as a carefree ladies’ man, the world’s most eligible bachelor. 

Yet one biographer’s dogged research unearthed an early marriage he tried to hide despite fathering two sons and a secret gay affair at a time when homosexuality was considered a crime.

Such conflict may have been personally damaging had it emerged back then. Instead, Sir Thomas Lipton’s career only thrived on his consummate myth-making. 

His legend began in the overcrowded slums of the Gorbals where he was born on May 10, 1848 – or 1850. Historians still cannot agree on which year, and both are referenced in textbooks. 

The youngest of five from a farming family who fled the Ulster potato famine in Co Fermanagh, his siblings all died young, leaving young Tommy to work in his father’s small shop, which sold ham, butter and eggs.

On leaving school, he worked as a cabin boy on a steamer running between Glasgow and Belfast, forging an early passion for ships and the sea. Crew members fired his imagination with tales of the United States and in 1865, Tommy had saved enough to pay for a passage to America.

He stayed for five years, working on a tobacco plantation, as a door-to-door salesman, a farmhand, and, finally, as a grocery assistant in a New York department store. It would transform his life.

He learned America’s ‘pile ‘em high, sell ‘em cheap’ philosophy, eye-catching marketing techniques, and how buying goods direct from the producers, thereby cutting out ‘the middle man’, allowed him to turn a tidy profit on small margins.

Returning home in 1871, he opened his first shop in Glasgow’s Anderston area, working 18-hour days, often sleeping on a makeshift bed under the counter.

Within ten years, he established a chain of stores across the UK using his mastery of the publicity stunt; he would stuff giant cheesewheels with gold sovereigns and sell them off in portions to clamouring crowds, and have pigs walked to his shops bearing a banner declaring, ‘I’m on my way to Liptons – The Best Place in Town for Bacon’.

Always looking for new opportunities, he alighted on the foodstuff still linked to his name today: tea.

Once a precious commodity worth more than gold, its price had tumbled by the mid-19th century and it fast became the beverage of choice of the Victorian middle classes.

Lipton sought to break the stranglehold of the London teabrokers by buying his own tea plantations in Ceylon (now Sri Lanka) and importing his own branded tea direct.

By the 1890s, his grocery empire had brought the Lipton name to the most fashionable streets of Victorian London and its multi-millionaire founder was mixing with the cream of Victorian society at his new mansion at Osidge, Southgate.

He was celebrated for his philanthropy, stepping in with a £25,000 donation (£2million today) to save a last-minute charity feast for the Queen’s diamond jubilee celebrations in 1897 organised by Alexandra, Princess of Wales. The following year he was knighted and later created a baronet.

‘He becomes overnight an A-class celebrity,’ Laurence Brady, director of children’s charity, the Sir Thomas Lipton Foundation, told a BBC documentary.

‘And all those other characters and skills he has... he is so charming and he’s so easy to deal with. Everybody loves to be with him.’

He claimed to have never married, insisting no one could match up to his beloved mother, Frances. The truth was far darker, according to biographer James McKay.

His 1998 book, The Man Who Invented Himself, recounts Lipton’s shotgun marriage to teenager Margaret McAuslan, an illiterate millhand who seduced him when he was 22 and already running his first shop.

When McAuslan discovered she was pregnant, the couple married. Lipton, a staunch Presbyterian, was so ashamed he gave his address as a cheap lodging house. Their son, Thomas, was born seven months later, on Christmas Day 1871, but died aged ten months of bilious fever.

Their second son, William, was born in September 1873. It is understood that shortly after the birth Lipton paid his wife and child to move to America, where McKay learned his son became a preacher and died in New Jersey during the 1920s.

During his brief marriage Lipton was already involved with William Love, his gay lover, whose name he passed on to his second son.

Together as manager and cashier the pair ran Lipton’s burgeoning business and after the break-up of Lipton’s marriage, Love moved in with Lipton to a large Glasgow flat at a time when homosexuality was still a crime.

Later they shared a huge house called Johnson Villa, which Lipton had bought for his parents in Cambuslang, Lanarkshire.

Love became Lipton’s confidant and companion and would rise to become general manager over the next 30 years.

‘Lipton lied about almost every aspect of his life, from family origins to his date of birth,’ McKay said. ‘There is ample evidence that Lipton covered up his only marriage and little doubt that his relationship with his general manager was of a sexual nature.’

The two men stayed friends after Lipton’s move to London, with Love allowed to remain at Johnson Villa and gifted ownership of several Glasgow stores.

Love would make occasional visits to London to see his old companion in what had diminished to a simple friendship. The pair eventually fell out when Love announced he planned to marry at the age of 70 and in a fit of pique, Lipton evicted him from Johnson Villa.

In public, Lipton’s popularity never waned and he used his fortune to pursue his passion for yachting and, in particular, the America’s Cup.

He had built at vast expense a succession of sleek yachts named Shamrock (to reflect his Scots-Irish roots) and would throw lavish parties aboard his luxury steam yacht Erin where the guest list included President Roosevelt, Kaiser Wilhelm II, and eminent scientists Edison and Marconi.

Yet, despite his wealth and influence, every challenge ended in failure.

Ironically, on at least three occasions, his American rivals’ boat was skippered by a Scot, Charlie Barr, who was born just a few miles down the Clyde at Gourock.

For Sir Thomas Lipton, there was only the consolation cup presented to him the year before his death in 1931. Now even that is gone.

The stores, too, have gone, and with no living relatives to pass his fortune to, he left the bulk of it to benefit the poor of Glasgow. Sir Thomas was buried beside his family in Glasgow’s Southern Necropolis. As for his legacy, Lipton’s Tea alone survives. Now owned by Unilever, it is still America’s favourite tea brand, worth around £8.35billion.

But what of the famous tea man’s lost cup? Will it ever be recovered?

Like the witty inscription on the golden trophy, the search seems to have failure written all over it.