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The Michael Lee-Chin Crystal during its unveiling in 2007.Tim Fraser for The Globe and Mail

On Oct. 5, Tariq Fancy stood up at a CBC Radio mayoral candidates debate, and posed a question to Joe Pantalone. "Look, I've just returned to Toronto after spending nearly 15 years abroad," the Toronto-born investment banker said. "I have lived in New York, Paris, Singapore, and Dubai, and during that time I got the impression that Toronto lacks a brand." What were the candidates' visions for Toronto's brand on the world stage, he asked, and how would they realize that vision?

Considering how readily Mr. Pantalone and his competitors have touted Toronto as a "world-class city," Mr. Fancy had every right to expect a well-thought-out answer - instead of the predictably vague and half-hearted responses he got.

World-class city. Let those three words roll around your tongue a bit. Feel the romance. Savour the power. Even before the mayoral election, the term "world class" was bandied about Toronto in reference to our architecture and our arts, our highways and our hot dogs, with both endearing sincerity from our boosters and scathing sarcasm from critics.

Torontonians who have lived abroad in renowned cities such as Tokyo, London and New York can attest that none fret over their global status as much as Toronto does.

The roots of Toronto's world class obsession reach back to the late 1970s, when the sudden threat of Quebec separatism caused a shift of capital and population that altered the power structure of Canada forever. Suddenly, Toronto, which was always the second city, became top dog.

"I think Toronto woke up one day, and found itself the largest city in the country," says Michael Davie, a Hamilton-based publisher, who wrote the book Why Everybody Hates Toronto. "We had this inferiority complex, and had to ask ourselves, 'Are we any different from a big bland city like Milwaukee?'"

Without the confidence to grow in our own skin, we cast ourselves onto the world stage in comparison to others, boasting that we were the Chicago of the North, New York run by the Swiss, or London with Better Teeth, and uttering the phrase "world-class city" so often, we hoped it would be a self-fulfilling prophecy.

Over the years, we have pursued "world class" status with rhetoric, infrastructure, and architecture. The most iconic symbol of such striving is the CN Tower, a totem pole to end all totem poles, our very own phallus of Babel. Other structures with world class ambitions followed: SkyDome, Pearson's Terminal 1, and the ROM Crystal - each touted as a game changer that would put us on the map, each disappointing us more quickly than the last. We became the Great Gatsby of municipalities, trying to buy our way into the upper echelon of cities.

We hung our dreams on bids for the Olympics, as if having the world arrive at our doorstep (as if it doesn't daily) would seal our global appeal. Years ago, former mayor and political columnist John Sewell blasted then-mayor Art Eggleton in the pages of The Globe and Mail for chasing world-class dreams while the city decayed. "Is Toronto a world-class city or is it not? It used to be that if we only had a domed stadium, then the world would know. Then a Grand Prix Auto Race would provide indelible proof. Now there's a new challenge to prove our worth to the rest of the world: the 1996 Olympics."

But our particular brand of striving, while admirable, may, in fact, be misguided. "World class" is an elusive and amorphous title: We know Paris and London have it and Dallas doesn't, but we have no perspective on our own city, and our collective insecurity means the goal line shifts with our self-esteem, remaining always tantalizingly just out of reach. What's more, even if "world class" is something we can arrive at, maybe the definition isn't what we think it is.

Saskia Sassen, professor of sociology, co-director of the committee on global thought at Columbia University, divides city rankings into two categories: World Cities, which are places that conjure up a romantic image and emotional attachment, such as Venice, Kyoto, or Buenos Aires; and Global Cities, such as Houston, Singapore, and Frankfurt, which rank competitively based on data sets, such as GDP, purchasing power, the number of corporate headquarters and business class hotels, and other quantifiable metrics. (She isn't fond of cities calling themselves "world class," a term she associates with chamber of commerce marketing.)

The best cities, according to Prof. Sassen, combine elements of both categories: marrying the tangible attributes of a Global City with the je ne sais quoi of a World one. And some of the things that make a city worldly have to occur naturally: the small coffee shops, indie rock bands, and thriving immigrant neighbourhoods that give cities like Toronto their appeal.

"It has nothing to do with history, architecture, or a geographical site. What's unique about Toronto is its ambience," says Joe Berridge, a senior partner at Urban Strategies, an international urban planning and design firm based in Toronto. In other words, "world class" designation is sometimes something that we can plan and campaign for, but most often is it bestowed upon places by an unspoken consensus, a feeling visitors get when they spend time somewhere special.

If we needed empirical proof that we should stop worrying - and we seem to - the most recent ranking of world cities, put together by PricewaterhouseCoopers and the Partnership for New York City, places us at No. 1 in the category of "Livability." We're high up in "Skyscraper Activity" (No. 2, after Tokyo) and "Economic Clout" (No. 4, after London, Paris, and New York). When all categories are averaged out, Toronto tends to hover around the top 10 or 12, jostling with middleweights such as San Francisco and Copenhagen for pole position.

Mr. Berridge recently attended a talk with New York's Mayor Michael Bloomberg, whose administration has worked with Urban Strategies on parks in Brooklyn and Governor's Island. Mr. Bloomberg, a man fond of calling New York the "Greatest City In the World," stressed that New York needs to work doubly as hard to remain a world-class city. Today, competition between cities is a global affair, and no one can afford to rest on their laurels.

"Toronto has to be world class, or we might as well fold our tents," says Mr. Berridge. Talking about it, obsessing over it, and doing everything we can to make our pronouncements a reality is something we should be doing a lot more of, Mr. Berridge insists.

Others, however, think we ought to stop harping so loudly about the issue, because the louder we harp, the less convincing we seem. "If you are world-class, in my view, you don't need to say it," says Margaret MacMillan, a native Torontonian and professor of history at Oxford, "Everyone else simply recognizes it. Great singers do not go around telling everyone that they have beautiful voices and nor do great beauties tell everyone they are gorgeous. To do that at all sounds insecure and as though you suspect that no one is going to believe you."

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