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If there is one thing Naheed Nenshi has never lacked it's confidence. Asked what Calgary's chances would be if the city decides to bid for the 2026 Winter Games his answer is quick and unequivocal.

"I'm quite convinced that if we bid for them we'll get them," the mayor said in a recent chat in his City Hall office.

He's likely right. The International Olympic Committee loves the way Canada runs these mega-extravaganzas. The Vancouver Olympics in 2010 is arguably the greatest version of the Winter Games ever staged. In any ranking, Calgary's 1988 show wouldn't be far behind. The IOC craves the stability that comes with dealing with this country. There is very seldom any drama or unpleasant surprises.

But are the Games still worth fighting for? That's the biggest question facing Mr. Nenshi and his council, one for which there is no simple answer.

There is little doubt the Olympics can provide a city, a province, a country, with an emotional and economic lift. People in Vancouver were genuinely depressed when the circus left town seven years ago, so wonderful was the party and the memories. And to be sure, you can look around the city and see all sorts of tangible benefits left behind: brand new hockey and curling rinks. The Richmond speed-skating oval is an architectural jewel and now an incredible community recreation centre.

But then, the Vancouver Games were exceptionally well managed. There were no nasty financial surprises when they were over. And there could well have been in the hands of an executive not as talented as the one that oversaw those Olympics, especially amid a global financial crisis.

Still, for all the potential benefits, there is still something that feels unseemly about dealing with the IOC, an organization laden with corruption, imbued with arrogance and entitlement. You really feel like telling them: keep your Games, you tiny, horrible, faux aristocrats. Why should anyone pay for you and your cronies to fly around the world, expecting to be dined and feted by cities looking for the honour to spend billions to host the Games? The entire bidding system is just so horribly archaic and vulnerable to abuse. Wouldn't it be wonderful, I've often thought, if everyone just said, "Forget it, we don't want your Games under these circumstances."

Then I jolt from my daydream and realize that will never happen and get on with my day.

As for Calgary, the mayor believes the Games could be staged for much less than any recent Olympics because most of the facilities built for 1988 are still in good condition. More debatable is the matter of whether staging the Games is the prudent thing to do.

"What I've heard from citizens, and what I personally believe is, if we are having to take on any deficit then it's a no-go," the mayor told me. "So the IOC really needs to make sure that the host city is not responsible for the upgrading deficit, which could be as much as $400-million. So if we can't fix that then I think we're out of the Games."

But the mayor added: "I think we're going to be able to solve that."

Yet that's only a small part of the mayor's challenge. He has to persuade Ottawa and the Alberta government to cough up about $1.2-billion each, amid conflicting reports about just how economically beneficial these Olympics will be for the city and country. There is also the not-so-small fact that the province is just emerging from a horrible oil-slump recession, which has left it with a pile of debt.

Jason Kenney, the leader of the United Conservative Party, has already declared his opposition to any bid on the basis that the province can't afford it. He is already planning to make fiscal stewardship the heart of his election campaign in 2019, setting his sights on the billions in arrears Alberta is in because of what he insists is the "incompetence" of Premier Rachel Notley's NDP government. A decision by the NDP to give Calgary more than a billion bucks to host the Games plays right into the narrative Mr. Kenney is crafting.

However, there remains a decent argument that Mr. Nenshi's town could use a party after the grim run it's had recently. Calgary hasn't fully emerged from "the troubles" yet but things are definitely trending in the right direction. The Olympics could give people here something to rally behind and look forward to.

I have no doubt what the mayor would love to do.

"I'm a big Olympics nerd," he told me. "I go to the Games. I have buddies and that's what we do every four years. I love hanging out at Canada House with the families and the athletes."

So if Calgary does host the Games, you'll know where to find him.

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