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An inflatable cowboy looks out over visitors at the Calgary Stampede on Sunday, July 6, 2014.

Jeff McIntosh/The Canadian Press

Two prominent Calgary clubs share nearly the same name but couldn't be more different. There is Ranchman's Cookhouse and Dancehall, which is part of the unbuckled stereotype of the Stampede: a 10-day epic binge of libation and libido that wreaks havoc with livers, STD statistics and marriages.

Across the Macleod Trail at the Ranchmen's Club, however, you'd find a more buttoned-up version of the classic event. Established in 1891, this wood-panelled, members-only establishment was championed by Sir James Lougheed as Calgary's answer to Montreal's St. James Club and became the stomping ground of the city's early oligarchs. Its oldest surviving members, called the Kremlin, play cards here every Wednesday, and it's also where members of newer powerhouses and descendants of old powerhouses – Cross, Macleod, Mannix – do a little business beneath a plaque of a member's brand or paintings of an idealized West. (No notes or papers allowed here, only handshake deals). The networking here reaches fever pitch around this time as oil executives, Stampede leaders and diplomats sit down with flimsy paper plates full of food and some solid agendas.

The two Ranchmen may have different definitions of hooking up, but come Stampede time they are equally important to the city. The event is not just a dream vacation for prairie hedonists or rodeo spectators. It's also vital to the city's business class. Calgary transforms into a giant trade fair, a real-world LinkedIn collision of schmoozing and boozing that's critical to the city's – and in turn, the country's – economy.

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"Stampede isn't just a spectacle. It's a culture," former Stampede president George Brookman told me at the venerable Ranchmen's as I tried my first prairie oyster. "It's not just about cowboys and chuckwagons. There is much more to it."

I was explaining to Mr. Brookman that I was a Toronto bumpkin who like many Canadians had never been to Calgary, let alone the Stampede. Were the rodeo, chuckwagons and grandstand really just one long excuse for self-abuse or was there more to it? Did the city's rapid response to the flood last year create a halo effect for this year? I was there for a 48-hour inhalation of a city that I always respected from afar but never understood.

By coincidence, I had bumped into the right person. The CEO of the printing company West Canadian, Mr. Brookman is known as Mr. Calgary. Tell people you've hung out with this force of nature and they ask you how exhausted you are. People urged him to run for mayor, but he didn't need the two-in-the-morning irritations that come with the extra power. Spend a few hours with him and the idea seems obvious. He charges through the Stampede and knows everyone's name, whether he is a CEO or a door-opener. That high-low sensibility carries over to his conversational style, which toggles madly between sacred and profane.

A major arts devotee, Mr. Brookman sees the Stampede going to the next level. On one hand, it's creating a year-round agriculture education centre. He also explained how he overcame some resistance among some traditionalists and championed art. He raised $2-million to bring kid-friendly bronze horse sculptures to the fairgrounds and led the charge for an impressive venue for regional painters and musicians called the Western Oasis. "I didn't want somewhere that people went on rainy days. I wanted a destination for real art."

Talking about the Stampede's challenges for the future, he said it was its ability to constructively engage animal-rights activists. Already the Stampede was under criticism for the death of a horse. "It's as if they think we don't care that an animal dies. Of course I feel emotional about it. It's terrible."

As for the more lurid side of the Stampede, he offered some wisdom: "If you're a young man at the Stampede and you're not getting laid, you are lazy."

While breaking off some peanut brittle ("A little hard," he said), he gave me a history lesson on the Stampede. "Just imagine that the world's most testosterone-driven event in the world was created by man named Guy Weadick." An American, Mr. Weadick brought the idea of a stampede to Toronto and Winnipeg, but both cities turned him down. Eventually he persuaded four of Calgary's wealthiest men – Ranchmen's Club members – to kick in some money and the first Stampede appeared in 1912.

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In hindsight, Toronto or Winnipeg could have sustained the event for a time, but only that Calgarian alchemy of mutual trust and unfettered moxy could keep the self-declared "Greatest Show on Earth" going. The oil would come later, and a gusher of money, but the Stampede forever branded Calgary as Canada's cowtown.

Like New York or Dallas, Calgary is a city of newcomers, which in many ways levels the playing field when it's not Stampede time. No matter who they are, they have bought into the idea of what Calgary means and bring an entrepreneurial vigour to it. Add Stampede gear to the mix and that becomes the other equalizer. Walk around the grounds and you see South Asians, Africans, Filipinos in jeans and boots and hats, a Sikh wearing a hat over his turban. Clothes, not multicultural messaging, become the lingua franca. It's a 10-day melting pot.

Overheard at the rodeo:

These are the most comfy shirts because the fabric is light and they only have one seam, so you can lift your arms, like this! That is my insight for the day.

Businessman in checkered shirt #1: I have four leads already. Big ones. The key now is to delegate.

Businessman in checkered shirt #2: Delegating is key.

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If cowboy outfits are the equalizer for socializing, the casual dress takes the self-importance out of networking. Having a discussion in suits at the Air Canada Centre in front of a Maple Leafs game may not be the loosest setting, but put two executives or sales reps in outfits at a rodeo or chuckwagons and no one can take one another too seriously.

"When you're back in the barns with your client and real cowboys, it's all very informal," said Scott McArthur, Fluor's general manager of business development and sales, in his corporate box while the rodeo was blaring in the background. "It's building new relationships or seeing people you haven't bumped into in a year. It's not transactional."

While there is much waxing over the Stampede's barrier-breaking culture, its Stampede leadership has created high-end hosting venues such ground-level boxes and more recently, two grandstand eating clubs, Ranahans and the Lazy S, which complement each other the same way as say, the Westin and W hotels. The former is more traditional, the latter more boutique-hotel urbane where you can take a table for $12,000 for the 10 days. The price includes food, but not booze.

For the casual but imposingly big Halliburton executive John Gorman, Stampede is a critical time to host bosses who've flown in from Denver or clients from far-flung countries such as Japan, where companies give employees family travel vacations to the Stampede and Banff as bonuses.

Mr. Gorman, the company's Canada-area vice-president, said that in general, the networking is "a precursor to a lot of business getting done," but as he also explained, it's a good time to have constructive conversations in a less-charged environment. "Look at it this way: I can take a CEO of an oil company to have a serious discussion at Ranahans about what we're doing on his properties," he said. "It's good to be able to have a frank talk in that kind of environment."

As he and business development manager Tom Pierce explained in an office that overlooks the sweep of downtown Calgary, there is also an etiquette to whom you entertain. "I invited a guy in the oil and gas to the infield. He said he'd love to, but we're in the tender process with your company."

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During Stampede time, Mr. Gorman and Mr. Pierce circulate in the grey margins of entertainment and work. Their Outlooks are stuffed. Further down the food chain, where there are more bosses, it's a little more nuanced. In the old days, two former Exxon workers tell me, the company would give them a few hundred dollars to go spend on the town. Nowadays, there is no free-roaming cash. It's more disciplined. The general sense I got was that middle managers could stray from work but not for too long, and if they do, they have to justify their absence. And they have some must-attend corporate events. "The work is more flexible than usual, and we have corporate events we go to," said Tanya Vetter, the lubricants manager at Imperial Oil.

When I gave her a puzzled look about her title, she said not to bother making jokes. She'd heard them all. After all, it's Stampede.

I invited some people out to go to a shisha bar. A few days later the boss of my firm says to me, 'I heard you've been enjoying yourself.' I said I was having a great time. He then says, 'I heard there were some strippers and hookers.' I wondered what he was talking about. And then I realized that something got lost in translation. It wasn't strippers and hookers. It was shishas and hookas.No matter if you're at the famous slosh pit Cowboys or at a tony party hosted by the Blakes law firm on a lawn at Fort Calgary, there is a lot of stumbling, but there is also some etiquette to it. If someone bumps into you, they take your arm, look you in the eye, and sincerely apologize. "In Toronto they'd just punch the other in the junk," said a transplanted lawyer from Ontario after someone jostled me.

George Brookman said a New Orleans official once remarked the difference between Mardi Gras and the Stampede was that in New Orleans, they have to dispatch thousands of policemen with clubs to keep the peace. In Calgary, they just need a 71-year-old grandmother to control the crowds. "All she has to say is 'Don't do that, boys,' and they don't."

Calgary may have outsized ego and ambition, but its small-town manners even out the bravado. I wanted to meet headhunter and woman-about-town Catherine Brownlee, who I had heard receives a hundred party invitations. I thought she was at the Stampede grounds but I was wrong. Mr. Brookman stuck me in his new black Beetle convertible and drove me 40 minutes out of town to see her – but not before he showed me his new prized possession he shipped in from New Mexico: a giant sculpture of a red bird, which he stuck in the middle of his parking lot.

I met Ms. Brownlee at a party held in a garage of Nortruck, a distribution company located in an industrial park. Blunt and vivacious, she told me how she sifts through her invitations: She calls around to see who is going where, if she has friends who are going, and figures out where the best opportunities are. Like many Calgarians I spoke to, she also wants to know if there is a charitable angle, an opportunity for non-profit matchmaking. To pace herself, she tries not to drink before 4 p.m.

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It is past 4 p.m. Running late to meet her friends at a whiskey bar, she offers to give me a lift in her BMW back to the city. As we drive, we talk about the light comedies of her life and her flagging career as a matchmaker: The number of eligible bachelors was declining, she lamented. It is a very New York conversation, suggesting that Calgarians are like New Yorkers without the neurosis and with a remarkable level of trust.

Calgarians, someone told me, are friends until they are really friends.

Stuck in Toronto-like traffic, Ms. Brownlee starts making calls and apologizes.

"You're also going to be late," she tells me. "Here's what we should do. You're going to drop me off, go to the Stampede and pick me up later. How does that sound?"

"In your car?" I said.


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