The forgotten tale of the 5ft Scottish fisherman who took on the world, became Kaiser Wilhelm’s nemesis and set the standard for Sir Ben Ainslie in the America’s Cup

It’s a four-kilometre walk up the Barcelona coast from Ben Ainslie’s America’s Cup base to an apartment overlooking the Mediterranean Sea. Within it you will find the descendant of a man who was quite remarkable and is long forgotten.

Folk don’t talk so much about Charlie Barr anymore. Not at all, really. And to Alasdair Purves, his great-great grandson, that has been a little puzzling whenever he has stepped onto his balcony across the past few months.

He has watched the America’s Cup trials play out from that very spot on the waterfront, so he is well aware Ainslie and his INEOS Britannia crew are close to making history. Indeed, if all goes to plan over the next 10 days, commencing on Saturday, Ainslie will lead a British team to victory for the first time in the 173-year lifespan of sport’s oldest international trophy.

But he wouldn’t be the only skipper from our shores to pull it off. To date, that is a distinction held solely by Barr, a five-foot tall Scot who won the Cup three times in succession in 1899, 1901 and 1903, albeit with the devilish footnote that each of them was at the helm of American yachts and achieved against boats flying the Union Flag.

Where 16 British teams have lost in the final since 1851, with many others failing to make it that far, this working-class lad from Gourock did more than any single individual to cause their defeats.

Barr was Scottish but he won the Cup three times for the United States in 1899, 1901 and 1903

His tale, from rows and wagers with Kaiser Wilhelm II to acts of fearlessness in the name of romance, is rather fabulous. But it is also one that has been largely lost on the breeze.

‘I met Ben Ainslie recently,’ says Purves, who is 42 and emigrated to Barcelona from the south of England a few years back to work in the sailing industry. ‘I told him I have an ancestor who won the America’s Cup three times and after a couple of clues, he smiled and said: “Charlie Barr”.

‘He knows his history and I really liked that because Charlie has been largely forgotten beyond a few sailing historians, a bit airbrushed out.

‘I went to the America’s Cup museum here the other day and was watching a potted history of the Cup. It included Grant Dalton, a sailing legend who runs the New Zealand team that are going up against Ainslie.

‘They have won the past two, so he’s in the film saying no one’s ever won this thing three times in a row and I sort of rolled my eyes. I’d like more people to know exactly what went before.’

As Ainslie prepares to lead his team out on to the water, driven by £250million in funding from Sir Jim Ratcliffe, Barr serves as a fascinating snapshot in time.

Born in 1864, he wasn’t from a privileged family. ‘His mother died when he was four and his father didn’t want him going to sea, so he put him to work in a green grocers,’ Purves says. ‘Eventually he followed one of his brothers into fishing and there’s a great story I only found recently when looking over some microfiche from a long-defunct newspaper in Rhode Island.

Ben Ainslie will captain Great Britain’s INEOS Britannia team against Emirates Team New Zealand in the 2024 Cup match, a 13-race series taking place this month in Barcelona

Great Britain has not won the America’s Cup in 173 years of trying – and no boat carrying the British flag has competed in the final since 1964

‘It happened off the coast of Scotland when he was about 14. The boat was caught in a terrible storm and taking on water as it was blown further and further out to sea. The older guys were collapsing with exhaustion and eventually this skinny kid grabs the tiller and brings the boat in through these crashing waves. He was credited for saving the whole crew and that was a pivotal moment in his early life.

‘After that the local crews wanted him onboard. In 1884 his half-brother got a gig to deliver a yacht across the Atlantic to New York for a Scottish businessman, who was making wagers with other wealthy gents over there that his boat would wipe the floor with anyone. Instead of Charlie heading back he stuck around to race for him and they won every one of them. He was then invited back the next year and they won every race that year as well.

‘Where it got interesting was when he raced a boat designed by Nathaneal Herreshoff – to give you an idea about Herreshoff, he was the Leonardo da Vinci of yacht design and would become one of the greatest ever. But suddenly this crack skipper from Scotland beat one of his yachts in some regatta, in a boat that really shouldn’t have won, before disappearing off again to do another season of fishing.’

Such was Barr’s reputation at this stage, the dominant New York Yacht Club and the Wall Street giant John Pierpont Morgan made him their skipper of choice and put Barr in a Herreshoff boat to steer their 1899 campaign.

By then, the NYYC had claimed victory in each of the 10 editions that preceded it, having clamped an iron fist around the Auld Mug since it was initially contested around the Isle of Wight in front of Queen Victoria in 1851. Of those wins, British yachts had been on the receiving end in seven, with programmes backed by an Earl, a knight of the realm, a Royal Navy lieutenant and a rail tycoon in James Lloyd Ashbury, who would go on to become a Tory MP.

The next Brit up for that 1899 race was Sir Thomas Lipton, who had risen from a Glasgow tenement building and was making fortunes in the tea trade. Pitting his Shamrock yacht against Barr’s Columbia, Lipton was trounced 3-0.

Ainslie, 47, is desperate to be the first captain to lead Great Britain to America’s Cup glory

Ainslie – who was born in Cheshire – previously worked as an tactician for Team New Zealand

The final in the next two editions, in 1901 and 1903, would see Lipton return to face the same man and a 3-0 whitewash was repeated on both occasions.

‘For the last of those, Charlie was racing a radical new boat called Resilience,’ says Purves. ‘This was the Herreshoff masterpiece, but it was so powerful, with so much sail area, it really needed to be kept on a knife edge. Herreshoff is quoted as saying Charlie Barr was the only man that could safely sail it and he delivered.

‘At that moment in time he was considered the greatest skipper in the world. I find it wonderful to think that this man from the west of Scotland was over in the US and being celebrated by the richest men in America. The likes of JP Morgan, William Rockefeller and Cornelius Vanderbilt all paid him well to lead their teams.’

While Lipton’s efforts to end Britain’s losing streak extended to two more losing finals, he would eventually be regarded as the only man to ever make good money out of an America’s Cup campaign – his tea sales boomed in the US, such was the attention garnered by his refusal to give up.

As for Barr, his focus changed tack, which is how an unusual rivalry with Wilhelm II, the ruler of Prussia, flourished. The Kaiser was obsessed with yachting and had suffered regular defeats to Barr and that laid the groundwork for a showdown when Wilhelm proposed a race across the Atlantic in 1905.

‘The Kaiser was a flamboyant kind of villain, quite bombastic,’ says Purves. ‘He put forward his best yacht, Hamburg, and crewed it with the best sailors in the German navy. Even though he wasn’t going to race it himself, he very much wanted to beat Charlie and prove Germany ruled the waves.

‘Charlie had been hired by Wilson Marshall to skipper his yacht, Atlantic, and ends up in a bet with Kaiser Bill. The Kaiser said to him, “If you win, you can have anything you want off my boat”, and Charlie chose the ensign off the back, the Kaiser’s flag of this great big eagle.

Ainslie has won five Olympic medals – one silver and four golds, including one at London 2012

Ainslie pictured with one of his Olympic gold medals at London’s Trafalgar Square in 2008

‘The backdrop to this is that Charlie’s wife was very sick with tuberculosis. I have retraced the steps through libraries and family histories and she had been given two weeks to live. He didn’t want to race, but his sponsor’s wouldn’t take no for an answer and offered to supply the best treatment money could buy.

‘Charlie agreed to do it and there’s this great scene that played out halfway through when they were hit by an awful storm. The saloon of Atlantic has flooded, and Mr Marshall, the owner, has lost his nerve, ordering Charlie to slow down and play safe. Charlie’s response was apparently to say, “You hired me to win this race” and then locked him in the saloon! He went on to win and took the Kaiser’s flag.’

The record Barr set for that crossing from Sandy Hook to Cornwall – 12 days and four fours – remained unbeaten for 75 years, but Barr’s legacy seems to have faded quicker.

Time will tell if Ainslie can emulate his America’s Cup achievement in the next fortnight, or if his collaboration with Ratcliffe will follow the pattern of so many other teams from these parts. Alas, they have already set a high mark by delivering a first British finalist since 1964.

‘I hope he and INEOS win it,’ says Purves. ‘The idea of Ben drinking Champagne from the same trophy as Charlie is really nice.’

It might also breathe fresh life into a forgotten champion.