John Tory’s family has long been Toronto high society — is it time for the city’s old guard to move aside?

1989.

A day in June.

Destination: SkyDome, as Toronto’s largest stadium was known then.

With a crowd 55,000 people deep, out to mark the opening of the radical new cathedral with the retractable roof, those who were there remember the lasers, the sky divers and the fireworks, but mostly … well … they remember the downpour. In a classically Toronto moment — cue the “Curb Your Enthusiasm” theme — the roof ended up jamming and some were drenched when the clouds opened.

Busybodies who were at the gala still bring up memories of that pageant of wet, yup. But what others remember is this: how much it was also raining VIPs. Awash in plutocrats, politicos and socialites — names including Koffler, Godfrey and Nugent making their mark — it functioned as a 1980s time capsule of who’s who in Toronto. To that end? One couple certainly in the mix (and staying dry in their box seats, namaste) were the late John Tory (Sr.) and his wife, Liz.

Indeed, the indomitable Liz — whom I once dubbed the closest thing to a dowager countess in this town — had been fairly instrumental in the lead-up to the whole thing, chairing the volunteer gala committee for the once-in-a-gen event.

Reading the tea leaves all these years later, after the tempest that has gripped our city in recent days — when their son, John Tory resigned as mayor of Toronto after copping to an inappropriate relationship with a much younger woman — I could not help but think of the elder Torys. And the family legacy, in general.

To the untrained eye, this might all register as simply a local politics story or merely that tritest of things — a sex scandal — but what struck me is how much it is also a story about a family brand. One family brand among a web of family brands that largely defined this metropolis for so many decades — criss-crossing spheres of business, politics and philanthropy — and how this represented a fraying that has been happening for a while of an old guard.

What would Liz have to say about this whole imbroglio? The one whose energy was unmatched at one point (“the term socialite does not really fit Liz; social powerhouse is more apt,” Rosemary Sexton wrote in her seminal 1993 tell-all “The Glitter Girls”) and who was never at a loss for words (“Liz is the most frank of all society women,” reported that same book). The one who is not seen much these days but is still about. (Last May, her son, the mayor, posted, “Happy Mother’s Day with much love and gratitude to my mother, Liz Tory, going strong at 90, seen here with great granddaughters Piper and Reese. Wishing a wonderful day to my mother, wife Barb and all mothers across Toronto!”)

Someone who is acquainted with the matriarch kind of gave me their best guess: “Liz always liked to know everything about everyone and usually did, so if this scandal was about anyone else she would be burning up the phone lines. That it is about her son, and affects his wife, Barbara, and their children … I can only imagine how embarrassed she is.” That whole canard about airing dirty laundry, etc.

Certainly, we have an inkling of what her late husband would have said. Co-founding the Bay Street law firm Torys LLP before moving to act as adviser to two of the most powerful companies in the country — the Thomson family empire as well as the communications behemoth built by Ted Rogers — he was famously of the Keep Your Head Down and Limit Your Own Publicity vintage. His namesake said as much when John died at his home in Florida in 2011.

“He used to shake his head at me when I was in politics because so much time was taken up by what was in the newspaper, magazines and on the radio,” Tory Jr. told Maclean’s at the time, although he stressed that his father was a big believer in public service. “He thought a lot of it — probably correctly — was unproductive. So he stayed away from it.”

Tory Sr. never did see his son become mayor of the city, but did see his challenges as the former leader of the Progressive Conservative party of Ontario, as you might recall. And Tory Jr. shared then that dad surely preferred staying behind the scenes.

Ahem.

Tory Sr., indeed, spent much of his career working on behalf of others who, like himself, were not publicity hounds. Lured in 1973 to work for the Thomson family’s holding company, Woodbridge Company, he helped Lord Thomson’s son, Kenneth, and later grandson, David, transform the business from a media company into a global giant, now Thomson Reuters. Although Tory officially stepped down from the job in 1998, he remained a trusted family adviser to the end, legendary business writer Peter C. Newman once describing John Sr. as “a kind of secretary general of the multibillion dollar corporate confederacy, prodding, solving, appointing, acquiring, divesting, troubleshooting, running the damn thing …”

Likewise, his relationship with Rogers, which he helped transform from a modest cable empire into a major player in wireless and beyond. “They were a great pair,” his son told Maclean’s (the son who also worked for Rogers, initially as a cub reporter at a radio station and later as head of the all-important cable division, and who still sits on the Rogers board). “Because my dad was so quiet and analytical whereas Ted was the consummate entrepreneur — colourful, impulsive and all the things my dad wasn’t.”

Liz, the matriarch, was no slouch either, as I mentioned. Her fingerprints are on so much in this town. A mother of four, she was a founding member of the board of the Metro Toronto Convention Centre. Likewise, she sat on the board of the Toronto Symphony for years. Together with her husband, she co-chaired the Brazilian Ball (for decades, the splashiest gala in Canada) one year and, another, ran the party for the 25th anniversary of the Shaw Festival.

Well into the 2000s — when I would see her around town — she was still massively engaged. Down with Luminato, the arts festival. Seen at openings at the Art Gallery of Ontario. Still holding her legendary Old Bags lunch, which raised oodles for Sunnybrook Hospital. And even, indeed, instrumental in getting the $130-million Ripley’s Aquarium off the ground. (It was Liz, the story goes, who gave the final fateful push to get Jim Pattison, the B.C. billionaire, to build the thing when Liz met him a dinner party years ago.)

This was the world from which the John Tory in the news these days famously sprung. In the parlance of today, he is a “nepo baby.” While a certain era of Toronto has been fading for a while — partly because of the passage of time but partly because, in the social media age, influence has shifted and there are simply many more orbits in what is a much bigger city — the bombshell of the last week makes me wonder if his resignation represents another tipping point.

Old society fixtures like Peter Munk or Galen Weston Sr. have died, after all. Families of the old WASP fiefdom — such as the Eatons — have contracted. The canteens that they used to frequent — think Bistro 990, La Scala or Prego Della Piazza — are long gone. Yet, spillover generations still cast an outsize influence here, be they Westons or Torys or Rogers.

Maybe, just maybe, we will eventually get a mayor who reflects a new Toronto, not a bygone one.

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

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