Royalty! Riches! And Hilary and Galen Weston’s greatest wealth of all: a 55-year-long love story

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It is 1991, an autumn eve, and Galen and Hilary Weston are in the midst of one the great double acts in the social history of the city: each a table of their own, inside a ballroom at Toronto’s Royal York.

To the left of Hilary — as the Nova Scotia salmon comes around, and goblets are eagle-eyed — sits Prince Charles. Next to Galen, at his constellation: a tiara-announcing Diana.

A you-had-to-there gala, held to benefit two charities — Pearson College and ABC Canada, a literacy group — the night is most remembered now among a certain set for some of the wry seating-drama that preceded it (“You can’t put people like Conrad Black and Peter Munk in the second row!”) but also for the dancing that later ensued. The princess in the arms of Mr. Weston. The prince with Mrs. Weston. The princess, again, with the then-socialist premier of Ontario, Bob Rae (their jive together spurred bemused international headlines). Notably, no dance between the prince and princess (already, in the throes of their fraying marriage).

“Toronto society won’t ever be the same since Prince Charles and the Princess of Wales graced it with their royal presence last Saturday night at a gala dinner-dance …” wrote columnist Rosemary Sexton at the time. I was still sowing my oats, so I missed the whole thing, but I know that was the night the Westons (who had just bought Holt Renfrew in 1986) cemented their status as “the king and queen of the Canadian Establishment” as Peter C. Newman once wrote.

And something I couldn’t help but think about when billionaire Galen died at 80 last week, putting an end, at the same time, to one of the all-time power couple arcs — in Canada, or anywhere. Unlike so many couples about whom that term is cavalierly thrown around, there was never a sense that she was an appendage (like so many society wives are), or that he was her purse-holder: they really did seem a genuine team over their 55 years of marriage, deftly combining both work and play.

Flush with the glow of the fortune-favoured, and a certain sang-froid that made it feel as if they’d just wandered in from an old Slim Aarons photo, Galen and Hilary seemed to have it all. But more than their vast fortune fluffed by a bevy of worlds (everything from Selfridges and Brown Thomas and Fortnum & Mason to Loblaw and Shoppers Drug Mart), or their many playpens (their leased stead in England that is Fort Belvedere, the Crown-owned former home of Edward VIII, where the King once abdicated, or their Valhalla dubbed Windsor, in Florida, complete with tennis courts designed by Stan Smith), it was something else that always struck me: just how good of a time they seemed to be always having. Together. Not anything to be taken for granted, given the vast gallery of the dour rich.

And, well, just how much of a wide berth they gave each other. Indeed, when Hilary was appointed Ontario’s Lieutenant-Governor (a post she anchored from 1997 to 2002), her husband was proud, even riffing on a quip once made famous by JFK: “I may not be the man who accompanies Jackie Kennedy to Paris, but I am the man who gets to accompany Hilary Weston to Timmins, Kingston or Kenora.”

It started in 1966. She was the ingenue from an Irish seaside town of Dun Laoghaire (pron. Dunleary), one of five children from a moneyless clan whose father had died when she was a teen. He was the tall tennis-playing golden child, three generations of a made-in-Canada mint (bread, man!), who one day spotted Hilary, then a model, on a billboard in Dublin (sporting hot pants!), and who finagled an introduction later at a dinner party. Theirs was a wedding held at Remenham Church, near Henley-on-Thames, complete with cruise down the river in a vintage steamboat (someone fell overboard — splash!). Theirs, too, was an early idyll in Roundwood Park, back in Ireland, complete with two children — Alannah and Galen Jr. — but one blotted by a kidnapping attempt by the IRA, which then had them eager to spend even more time across the pond (the IRA plot was botched due to a tip-off, by the way, the gun battle between police and the terrorists all happening while Galen played polo).

Scene-change: Toronto. Where Galen was needed, anyway, to help his father rescue the then-failing grocer, Loblaw Co. While it took Hilary some time to acclimatize — “Toronto is not a very welcoming city. I had no one — and Galen was so involved in the business,” she once said — her confidence eventually soared. Along with the trappings of their wealth. While her husband has always said the stylish Hilary was key to his business interests — especially in his more haute ventures — the ante was upped when she became vice-chairman of Holts, building on her involvement with Brown Thomas in Ireland, not to mention her ne plus ultra role in philanthropy, like leading a boffo capital campaign for the ROM (complete with a personal cheque of $20 million!).

Someone who got it: Graydon Carter. Having once given them a feature spread in Vanity Fair when he was the editor there (“Weston Civilization” blared the headline!), and having them on his usual roster for the annual VF Oscar party (where the couple would cross paths with everyone from Beyoncé to TaySwift over the years), it was a mutual appreciation society. Carter told me over email the other day: “I liked Galen and Hilary. A lot. They threw a wonderful dinner for me years back during the Toronto Film Festival. I even scouted restaurants with him in London.”

Did anyone have a good time as much as these two? Not many. From Art Basel, in Miami, one year, where Hilary and Galen hosted an exhibition opening for painter legend, Jasper Johns, to a stay on the Greek island off the Peloponnesian coast, where they schmoozed Carolina Herrera and her hubby, Reinaldo … to sitting with Prince Albert and Princess Charlene of Monaco to celebrate the centennial of the Ritz-Carlton, at a gala in Montreal. At Loulou’s in London, and Bymark in Toronto. The pics themselves tell the story: hosting Gwyneth Paltrow and Jake Gyllenhaal here, schmoozing with Julian Fellowes and Joan Collins there. See them now in their best formal wear at a party for 80 in London to celebrate the 70th birthday of King Constantine of Greece (a party that brought out more strands of European royalty in one room than there have been since).

The Frieze Art Fair. The Cartier Queen’s Cup. The Grano Speakers Series. They were everywhere, even after they had become grandparents. And poring over some old photos, I have one takeaway: as much as some of this might have been for “business,” it does not seem like Hilary and Galen, together, ever got jaded. They stayed interested. Wanted to be in the thick of it.

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In part, because they were such good dance partners.

“In a lot of ways, their courtship never ended,” someone who has worked with the Westons for over three decades told me last week. “It was always like they were on one long date.”

Shinan Govani is a Toronto-based freelance contributing columnist covering culture and society. Follow him on Twitter: @shinangovani