When Hilary Weston, former lieutenant-governor of Ontario and matriarch of the second-richest family fortune in Canada, leans in to speak, her clear, plastic, stick-figures earrings dangle. “Aren’t they fun!” she laughs. “Everybody adores them—my grandchildren . . . And everybody wants to tear them off my ears.” They’re made by Miu Miu, the Prada offshoot whose appeal skews so young its 2011 spokesmodel was 14 years old. And yet on Weston, who is 71, they’re somehow fitting. Although she hides her face behind oversized shades, Weston seems none the worse for wear for having hosted an art exhibition the night before and presided over a champagne-fuelled after-party.
She’s sitting on the courtyard balcony of the Westons’ Florida home in Windsor, the country-club gated community—complete with art gallery—in Vero Beach that she and her husband, Galen, founded in 1989. According to its planner, Andrés Duany, it’s “a little odd” to have “an emphasis on culture in a holiday place. But that’s the personality of the Westons.”
Windsor’s layout is orderly, the architectural code so strict it has turned off some potential buyers. In devising it, Hilary Weston says, “We wanted to create a special, unique experience that we would enjoy and our family and like-minded friends would appreciate.” The phrase “creating experiences” is one of her favourites—as if she sees herself as a curator for people’s lives.
And now the Gallery at Windsor is courting the world. Its new exhibition, presenting the surreal work of emerging Cologne-based twins Uwe and Gert Tobias, is the second of a three-year collaboration with the Whitechapel Gallery in London, where it will run in the spring. It’s the first Windsor-based exhibition to travel elsewhere. For next year’s exhibition, says Whitechapel curator Iwona Blazwick, they plan to bring in a “great master” of contemporary art.
Just as Windsor is inviting people in (by appointment, which is the only way to see the gallery), Hilary Weston is cautiously opening up. Since her governorship ended, she has kept a reserved public image while devoting much of her time to philanthropic causes, including the Hilary Weston Writers’ Trust Prize and the Canadian Ireland Fund, which she founded in 1978. In recent years, she has tended to speak only in a few heavily stage-managed interviews with luxury-lifestyle publications. But now, Weston is gingerly edging back into the spotlight. “I have a body of work,” she explains, “and I have something to talk about.”
On the road to Windsor from the airport in Melbourne, Fla., half of the properties have “for sale” signs. In the wake of the subprime mortgage crisis, the area’s name, the Treasure Coast (a 1715 Spanish fleet carrying silver was lost in the Atlantic Ocean nearby) seems ironic. But if you cross the Indian River to a barrier island, you’ll find something of a little utopia. It’s a vision of a tidier future: the 224 houses are all built close to its narrow streets and painted in muted colours; residents drive golf carts and wave as they pass one another; the village store and restaurants are cashless, accepting only customized cards. Even the palm trees, unlike their rough-hewn brethren nearby, have had their browning “beards” shaved.
The Westons founded Windsor on the site of a failed grapefruit plantation; it’s based on the New Urbanist tenets of Duany and his wife, Elizabeth Plater-Zyberk, who also planned the famed community Seaside, in the Florida panhandle. The idea was to build a walkable development with a vibrant, easily accessible town centre and houses that, although built closer together, retained privacy through a courtyard-based design.
“We toned down the colour palette radically.” What’s more, he says, Windsor eschewed “the kind of pseudo-classicism that is a plague in the more pretentious developments in Florida.”
This strategy led to their turning down “some very substantial sales, because the owner’s architect insisted on arches. I don’t know of any other developer that would have done that . . . simply for a belief in the visual integrity of the place,” Duany says.
Windsor offers a glimpse into the famously private Westons’ aesthetic sense and way of life. A walk around its 170 hectares reveals none of the expected ostentation. Although the community has super-rich and famous residents (such as two generations of Swarovskis and tennis legend Ivan Lendl, who plays on Windsor courts designed by Wimbledon champion Stan Smith), the architectural code “protects people from each other,” says Weston, “and they really like it.” The design philosophy seems to translate to Windsor’s other residents’ personalities too: according to former Toronto-Dominion Bank CEO Charles Baillie, who lives there part of the year, “It’s a really interesting group of people as you start to peel back the onion. No one is trying to impress you. It may be that all of us feel that we can’t compete with Galen and Hilary, but they’ve set a tone.”
Still, Windsor’s design has served to curb the New Urbanist ideal of forging a connection with the world outside. In the planning stages, Duany told the Westons they were working in “one of the safest places in America. And they said, ‘Yes, but we noticed that Seaside and other projects are full of architectural tourists peeking through the windows.’ ” He laments, “That’s the only flaw of Windsor. You can’t have a really vital town centre and not let people in.”
The Westons have good reason to value their security. In 1983, the Provisional IRA attempted a kidnapping at their house near Dublin; the police, having been tipped off, laid an ambush, and in the ensuing firefight, four guerrillas were wounded. “It’s not something I really want to talk about,” says Weston, her husky voice going even quieter than usual, “but I had young children”—her daughter, Alannah, was 11, and her son, Galen Jr., was 10—“and I think it was important not to be seen.” Six years after the attack, Windsor was built with a gatehouse.
And yet, for those without business or friends in Windsor, the art gallery beckons. It opened in 2002, at the behest of Alannah Weston. “I feel that if you don’t share with the locals,” she says, “or even with visitors, then somehow it’s less real.”
The gallery is now a reflection of her mother’s tastes. Hilary took it over in 2003, after Galen privately bought the high-end English department store chain Selfridges and appointed Alannah as its creative director. The matriarch takes her task seriously: at the launch of the Tobias exhibition, she closed the open bar after an hour or so and funnelled all the guests—who included Museum of Modern Art director Glenn Lowry and Princess Michael of Kent—downstairs for an onstage chat between Whitechapel curator Blazwick and the artists. None of the work at the Windsor Gallery is for sale, and despite the Westons’ own extensive private collection—which encompasses everything from Renaissance drawings to contemporary work by Alex Colville and Peter Doig—she asserts, “I don’t want to possess things. I’m just so interested in the mind—what goes on behind the making of the work.”
Some of the exhibition’s first visitors, she says, found the dreamlike, collage-based art, with disembodied heads grafted onto the bodies of insects and birds, “uncomfortable” viewing; she notes with satisfaction that it’s still “challenging” her. Blazwick praises Weston’s “fantastic eye.” Together, they went around Art Basel Miami, the famously manic art fair. “I’ve been doing this for 20 years, and she saw things that I missed,” says Blazwick. “She doesn’t take it for granted that someone is great, which I might do. It’s like having a great editor.”
A 2011 proﬁle of Galen Weston in the Financial Times characterized Hilary as an “unsung hero” of the family. “I don’t really agree with that at all, but it’s nice that they think that,” she says. Her family, she admits, did push her to take up the lieutenant-governorship in 1997. “Both my son”—Galen Jr., or “G2,” is the executive chairman of Loblaw Companies—“and Alannah said to me, ‘Mother, you’ve got to do it!’ ”
She recalls the objections that greeted her appointment. “The media just went hell-for-leather. I had to say, ‘Listen, I wasn’t born with a silver spoon in my mouth. I’ve worked hard all my life, and you don’t know me.’ ” Her father died when she was 17; with her mother chronically ill, she left school in Dublin—and along with it, her dream of studying drama in London—and modelled to support her younger siblings. And yet the press branded her an entitled trophy wife: Globe and Mail columnist Margaret Wente sniped that “millions of girls” might learn from her that “if they are lucky, they may meet an amiable, handsome young billionaire. (Don’t worry about higher education, gals!)”
In fact, she worked to reinvigorate the office of lieutenant-governor as more than a ceremonial role: “Being dressed up in fancy ball gowns, going into gala events, was not what I felt the office was about,” she says. She criss-crossed Ontario, visiting institutions she felt might need help or exposure, from women’s shelters to mental hospitals. “I would go quietly, meet with the social workers, visit the sanctuaries, and therefore learned a lot about where I could help or draw attention to it.”
Windsor too proved influential. It was a risk when the Westons had it built—Hilary recalls how “real estate agents thought, ‘This is not going to work, because we have never seen anything like this before.’ ” But in central Florida now, says Duany, “You can’t believe how many buildings look like Windsor. The genetic material of Windsor is extraordinary. You see the style everywhere.”
For her part, Weston says, “We’re passionate about this place; we’re passionate about the art, and it’s very nice for you to ask one to be interviewed. One only does things if we feel that it’s a benefit to the organization.”
It’s possible she learned her use of the third person from her friends in the British royal family—who are also her neighbours, as the Westons spend summers in Fort Belvedere, near the original Windsor, in England. But it also dovetails with her desire, when asked anything personal, to throw attention elsewhere.
Alannah recalls when she was 17, and starting to attend parties: “I said, ‘Oh Mum, it’s so intimidating going into a room full of people that you don’t really know. Does that ever go away?’ And she said, ‘It never goes away.’ ”
But when hosting a large post-exhibition dinner in the courtyard of the Windsor guest houses, Hilary seems in her element, drawing energy from others. And when she and Galen have said their goodbyes, as the artists hold court in the wee hours, Blazwick reflects on her friend’s “tremendous sense of fun. She likes the mischievous, and she’s not afraid of things that are rule-breaking. She’s not conservative—she’s open-minded.”
These aren’t traits for which Weston is known, although perhaps at this time in her life, she’s ready to let them emerge. In her stately transatlantic accent, she says, “Being Irish, I think, you don’t take yourself too seriously.”