“Toronto is on uncharted waters.”

Such has been the refrain here these past few days. You can hear it from the journalists who cover City Hall, the bureaucrats who work there, and even the city councillors themselves. Nobody has a whole lot of experience with mayors getting caught on video smoking crack. Everybody has been equally speechless when they view an even more damning video, released by the Toronto Star on Thursday, of a deranged Mayor Ford (that’s the only appropriate word) acting like a curious combination of the Cowardly Lion and Al Pacino in “Scarface.” In other words, the people who can generally be relied upon to put the city’s issues into context for the rest of us have peered out from the fore-deck of the municipal ship of state—North America’s fourth largest—only to announce that they have no idea where we are.

As everyone who watches “The Daily Show” or “David Letterman” now sort of knows, Toronto elected Rob Ford to be its sixty-fourth mayor, in 2010. Asking why a city of two and a half million mostly sane people would do such a thing makes for an interesting conversation.

The usual answers have to do with the political divide between urban and suburban notions of what a city should be. Or with the anger that the ordinary folks of the outer city reserve for the opera houses, bicycles, and liberal inclinations of the inner. Often, the discussion turns back to the controversial move, taken in 1998, to amalgamate six associated but distinct municipalities into what’s now known (ominously, I always think) as “the megacity.” Ever since, the old urban center—the polity that, with a certain wistfulness, is still sometimes referred to as “the former City of Toronto”—has been outnumbered by what it used to regard as its suburban satellites.

It is one such former satellite, Etobicoke, that Mayor Rob Ford has always called home.

Before becoming mayor, Ford had been a relatively obscure and isolated city councillor for a decade. He was known mostly for his ample size (Toronto journalists turn themselves in pretzels trying to avoid the most obvious adjective to describe him), his confrontational encounters with the press, and his dogged refusal to spend what he considered the excessively high office budgets given to city councillors. His commitment to frugality was enabled in part by the fact that, even though he styled himself an “ordinary guy” and man of the people, he is, well, rich.

When his (apparently delusional) hope of becoming a football player fizzled out, along with his intention to become a university graduate, he managed to find a well-paid position at his father’s successful label company. After showing very little interest in venturing too far from the woods behind the playing fields of Scarlett Heights High School, it wasn’t a great surprise that Ford decided to become an Etobicoke city councillor. Nor should it have been a surprise that his suburban credentials, conservative values, and family money helped him to convince the residents of Etobicoke, Scarborough, York, East York, and North York that their precious tax dollars were being frittered away at City Hall—which, of course, was downtown.

“Stop the gravy train” became Ford’s rallying cry, and even though the latte-drinking, media-controlling, tax-and-spending élite of the former City of Toronto did not share enthusiastically in the choice, Rob Ford was elected overwhelmingly. He was seen as the champion of the overburdened taxpayer—the suburban purveyor of common sense who, even if he was a little rough around the edges, knew what a dollar is. To this day, as his administration falters, Ford never fails to address his apparently unshakeable core. With no legal mechanism by which to remove him from office unless he is actually convicted of a crime, and with a base of apparently unshakeable supporters, he might actually get reëlected next autumn in order to make good on his promise to save taxpayers money.

So, as you can see, there are any number of ways to approach a conversation about Rob Ford. And in Toronto, during these past few surreal days, it feels as if every single one of them is being tested out, repeatedly, by every single person in the city. You can leave the conversation in one downtown Starbucks, walk fifty or a hundred feet to the next downtown Starbucks, and find yourself immediately back in the middle of the very same discussion. There’s been no lack of community involvement on this one.

But really, when you get right down to the nuts and bolts of the question—Why, exactly, did a reasonable kind of place like Toronto elect its current mayor?—you have to conclude that it doesn’t matter anymore. Why we did it is the least of our problems. The only point worth making at this juncture is that Rob Ford turned out to be a staggeringly bad choice.

The problem is this. Nobody knows what to do with a mayor who will not resign, even though he has ticked most of the boxes in the “You should resign immediately if…” section of the customary understanding between elected officials and their electorates. Such as:

If you smoke crack.

If you sometimes find yourself in the condition that Mayor Ford has now immortalized as “a drunken stupor.”

If you let late-night visitors smoke pot in your City Hall office.

If you consort with criminals.

If people with whom you were recently photographed—in front of a suburban crack house, it should be noted—start turning up dead, or splayed on the ground beneath windows from which they have just mysteriously fallen.

If you publicly malign the reputations of any politician, civil servant, or journalist who (correctly) raises the suspicion that the Mayor has a substance-abuse problem.

If you are seen reeling through the streets of Toronto on several festive occasions while being, in the Mayor’s own vivid description, “hammered.”

If (and it was this offense that seemed to really rattle many Torontonians) you urinate in public—or, to be fair, if you urinate in public enough to be captured on police surveillance cameras.

Oh, and about those police surveillance cameras: you should probably resign as the mayor of Toronto if you are the subject of a costly police investigation—during the same period that you, as mayor, will preside over the upcoming police-budget debates at City Hall.

All this has been particularly worrisome, especially for older voters. As you can imagine. There was a time, not so long ago, when “uncharted waters” and “Toronto” were words that only rarely appeared in the same sentence. Toronto was nothing if not predictable. But times change. And even when it unfolds in slow-motion, there’s nothing very predictable about an unqualified, jaw-dropping political disaster.

For example: I didn’t expect Rob Ford’s confession that yes, as a matter of fact, he did smoke crack—nor did his staff, or the startled media—when, apropos of nothing, the Mayor decided to admit what he’d been denying for six months. After what must have been an interesting internal debate, Ford apparently concluded that attributing his crack smoking to a drunken stupor would appear more mayoral than simply saying he liked to get high. I’m guessing he thought it was just a good time to get it off his chest. Nobody could have guessed that something so legally inconsequential would send so many ships adrift.

But here we are, bobbing along on what feels like a sea of identical conversations. From the literati assembled at this week’s Giller Prize gala in downtown Toronto to the drug dealers of East Etobicoke, Torontonians of all walks of life want to know: Who is the man in the first video whose off-screen voice goads Mayor Rob Ford, crack pipe in hand, to launch into his now-infamous homophobic and racist remarks? What’s on the mysterious second video? Is there now a third video? (At this stage, anything is possible.) Which is less forgivable: extortion, or urinating on a tree in a park? These are the kinds of questions—to our considerable surprise—that we find ourselves asking these days.

But no historian has stepped forward to point out a precedent. No elder statesman has reminded us of some previous historical episode with parallels to Toronto’s current crisis. It’s the one thing on which most people in Toronto agree. We are way out of sight of land.

David Macfarlane is a writer based in Toronto. A U.S. edition of his novel “The Figures of Beauty” will be published by HarperCollins next fall.

Photograph by Chris Young/AP/The Canadian Press.