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Top: Standing from left to right are Lord Lovat, also known as Simon Lovat; Catherine Nugent; Bruce Bailey. aldenbyPhoto by Trevor Haldenby

Though TIFF beckoned with red-carpet shimmer, a bespoke invitation thick enough to press flowers promised a more eccentric soirée. Bruce Bailey, an art dealer, venture capitalist and bon vivant, was throwing a party for a somewhat bemused Simon Fraser, The Rt. Hon. Lord Lovat and Chief of the Clan Fraser. By day, the 35-year-old commodities analyst works for a French hedge fund, where he goes by Simon Lovat: Not only does he have a series of titles to choose from, he has a selection of surnames.

In case people missed the Highland connection – the Frasers fought at Culloden – the keening sounds of a piper summoned them into a downtown oyster bar to nibble on Scottish smoked salmon and slurp oysters provided by the son of Summerside, P.E.I, Rodney Clark. The guest list included enough Westons, Blacks, Jackmans and Frums to bedazzle the most jaundiced partygoers. And if some of them were detained elsewhere, there was an eclectic blend of artists, intellectuals, and performers of various ages and stages, including the photographer Geoffrey James, visual artist Shary Boyle, Canadian Opera Company general director Alexander Neef, society doyenne Catherine Nugent and former politician Belinda Stronach.

"He's our Gatsby," a guest whispered affectionately about Mr. Bailey between canapés, while a jazz group played in a terrace corner. As for the guest of honour, he stood nobly while COC soprano Sasha Djihanian serenaded him with "O mio babino caro" from Gianni Schicchi and Mr. Bailey toasted him as a figure out of Jane Austen. With his erect carriage and smouldering dark eyes, Mr. Fraser could have played Mr. Darcy, the romantic swain of Pride and Prejudice, except that he wasn't surly and his ancestral lands had been sold to pay off the debts incurred by his forebears. The urge to restore the family seat thrums in his veins. Unlike his antecedents, who made their money fighting foreign wars in a burgeoning empire, he serves global capitalism, making his way buying and selling mining stocks for Carmignac, the hugely successful French hedge fund. Hence he, too, finds himself in Canada.

The Clan Fraser has a bloodcurdling past that includes an ancestor who was hanged, drawn and quartered next to Scottish patriot William Wallace (the Braveheart played by Mel Gibson in the Academy Award-winning film) in the 14th century, and another called Simon the Fox, who was beheaded at the Tower of London in the 18th century for his role in the Jacobite rebellion headed by Bonnie Prince Charlie. After their defeat at Culloden, the Frasers' lands were forfeited. It was said the English government left them "not so much as a cock to crow the dawn of day."

Determined to recoup the family fortunes and restore the clan, Simon the Fox's son (who, not surprisingly, was also called Simon) raised a regiment and changed sides to fight with British General James Wolfe on the Plains of Abraham in 1759. This was the beginning of a long and valiant intermingling with Canada that continues today with the Quebec-based ceremonial regiment, the 78th Fraser Highlanders.

When he is not trading mining stocks, the current Lord Lovat is the honorary Colonel in Chief, a role he assumed as a teenager. And therein lies another heartrending tale. Over a glass of wine, Mr. Fraser begins with his romantic war-hero grandfather, the 15th Lord Lovat, the swashbuckling character played by Peter Lawford in the film The Longest Day. He led a commando troop in the invasion of Normandy on June 6, 1944, accompanied by his personal piper, Bill Millen, who marched up and down Sword Beach pumping "The Road to the Isles" while the Germans picked off at least a dozen of his comrades. The Germans didn't shoot the piper "because they thought he was mad," Mr. Fraser said. Mr. Millen, who died in 2010, lived long enough to play the lament at his commanding officer's funeral in 1995.

By then, Mr. Fraser had suffered his own losses. Although the third of four siblings, he knew that he would one day inherit his family's hereditary titles. "Ask my sisters what they think about primogeniture," he retorted, deflecting the obvious question. But he didn't expect it to happen when he was 17, a student at Harrow, and more interested in girls and escapades than assuming the family mantle. In 1994, his father suffered a fatal heart attack when they were riding to hounds. "We had 200 horses behind us and a pack of hounds in front. I was next to him and he fell forward and his hat fell off. His last words were: 'Where are the hounds?'"

That's when he learned that his father, who had been trying to modernize the family business, had incurred massive debts. "We had to sell everything," he said. "Suddenly, all the assets that would have backed up this enormous responsibility disappeared – and I had nobody to tell me what to do."

Being young and callow probably saved him. "If I had had more emotional maturity, I probably would have been much more affected by it. But I just got on with it."

Speaking of getting on with it, Mr. Bailey – for all his bonhomie – adheres to his own timetable. As the clock struck 8:30 p.m., he pulled out a stash of manila envelopes from his breast pocket and paid off the musicians. On cue, a waiter passed with a tray of sweets. "Oh, here come the chocolates," somebody said. "Time to go." And the party moved on.

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