Voters make their way in and out of the polling station in Toronto in 2015. (Ian Willms/Getty Images)

I lived briefly in Toronto a few years ago, and it was a revealing experience. Suddenly, I understood where so many Canadian tropes came from.

Toronto is flamboyantly multicultural and aggressively trendy, a city where daily life does seem to be taking place in the permissive, postmodern country you read about in Economist cover stories.

Toronto also embodies classical Canadian insecurities. Like Canada itself, until quite recently the city was known mostly for being homogeneous, stuffy and dull; a city, all the tour books remind, once nicknamed “Methodist Rome”; a place where storekeepers shut their blinds tight on Sunday to prevent even window shopping on the Lord’s Day. The new Toronto has something to prove, grasping for relevance in the 21st century after being dismissed in previous ones. When locals recite oddly qualified boasts about things in “the fourth-largest city in North America,” you can hear the desperation.

Small wonder, then, that Toronto politics have been a source of such heated emotion. Film festivals and pride parades get you only so far; true world class-status requires a solid infrastructure of sane and respectable government. On this front, recent headlines remind that Toronto still has a ways to go.

Until 2014, the mayor of Toronto was Rob Ford, the babbling, perennially offensive right-wing populist whose chronic substance abuse issues (and unconvincing denials thereof) provided endless fodder for late-night comedians. Liberals blamed the Ford win on amalgamation, the ’90s-era process through which Toronto absorbed the more conservative municipalities surrounding its downtown core. It was a process that engorged the city with a heroic population but clearly helped suburbanize its politics as well.

Despite the often grotesque character of his reign, Mayor Ford’s small-government obstinance earned him credibility with Toronto conservatives, which, after his death, helped legitimize the ascent of his brother and right-hand man, Doug Ford. Elected premier of Ontario in June with the backing of “Ford Nation” (that is, middle-class north Toronto), Ford II now plans to religitgate old battles and use provincial power to prune the size of Toronto’s city council from 47 seats to 25, a move progressives find nearly as offensive as the Trump-supporting premier himself. The reform would give Toronto one of the most legislatively lean governments in Canada, prompting worries of further eroding responsible governance of a municipality once described as “both too big and too small.”

Premier Ford’s council reforms come just three months before Toronto’s Oct. 22 municipal elections, and the ensuing debate has helped overshadow the unfolding preposterousness of its mayoral contest.

Rob Ford was succeeded as mayor by John Tory, a man who, whatever other qualities he may possess, does not exude the status of a “world-class” leader. He lacks the ideology of a Bill de Blasio, the energy of a Rahm Emanuel, or the guts of a Sadiq Khan. He simply is what he is: a tired denizen of the Canadian elite elected as a compromise candidate promising normalcy.

Yet, no bolder figure from the city’s political establishment has emerged to contest Tory’s bid for a second term, a fact that has not only exposed a paucity of ambition in Toronto’s leadership class but also ensured that his two most high-profile rivals are firmly on the fringe.

Early polls have declared Tory’s most serious competitor to be recently resigned city planner Jennifer Keesmaat, who though well-known to city hall watchers, is hardly a household name.

As a bureaucrat, Keesmaat was said to have an arrogant style, which spiraled into self-parody last week when she tweeted that Ford’s council reforms would justify “secession” from Ontario. Though her tweets claimed to be clear-eyed (“Now that I have had a chance to sleep on it. Secession. Why should a city of 2.8 million not have self-governance?”), she has since sought to sow ambiguity. In a subsequent interview, she dubbed her words an “expression of … frustration, it was not a policy statement,” while still insisting “sometimes you do stand up and say enough is enough.”

“Enough is enough” is certainly the mantra of alt-right pundit Faith Goldy, who also made an 11th-hour filing to challenge the man she calls “Weak John Tory.”

Once relatively mainstream and well-connected, over the past three years Goldy’s politics have exponentially become extreme. She was previously a mainstay of the Sun News Network and Conrad Black’s “The Zoomer,” but her increasing comfort with the toxic vocabulary and characters of white nationalism has exiled her to ever-darker corners of the internet’s underground. Following widespread denunciation of her sympathetic coverage of the Charlottesville rioters, she was fired last year from Rebel Media after a cheerful appearance on a podcast run by the viciously anti-Semitic Daily Stormer.

Goldy’s audacious but significant candidacy — she is surely the highest-profile alt-right celebrity to seek elected office — is deeply embarrassing to the city and is likely to be ignored by its press and politicians. Years of celebrity have probably earned her more admirers than many care to contemplate, however, and her racialized rhetoric panders to real anxiety over surging gun violence. It would no doubt expose awkward truths about the city’s pretenses of unqualified tolerance if her run were  treated seriously.

In justifying his decision to spend a life covering politics, Charles Krauthammer once said that if you get the politics wrong, nothing else matters. Toronto has plenty of ambition, but at present its politics hardly look right.

Read more:

J.J. McCullough: The decline of Canada’s anti-Americanism

Michael Taube: The rise of Doug Ford in Ontario

David Moscrop: Doug Ford brings the American culture wars to Canada

Peter Loewen: Did Canada just elect a ‘Trump light’? Not exactly.

Doug Moscrop: Canada is not your utopia