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I want to like you, Toronto, I really do. After all, I know your reputation amongst Canadians not lucky enough to call you home, or worldly enough to assess you correctly. Still, you make it so difficult. What gives?

On paper, you look quite promising: Canada’s largest city, at around 5 million people; a diverse population of people speaking a symphony of mother tongues and worshipping at least a dozen deities; museums, art galleries, festivals, and seven professional sports teams; an integrated public transit system with streetcars, a subway, and extensive bus routes; the CN Tower, which is still a marvel after all these years.

And yet.

And yet, in practice, you suck. Not badly, don’t get me wrong. Just badly enough to make me bristle when one of your patriotic denizens pronounces on your status as a “world city.”

Not quite.

Barcelona, for example, comprises around 5 million people, too. It’s also situated next to a large body of water. It has not one but two official languages. Its museums and galleries and, ahem, UNESCO World Heritage sites blow your AGO and your ROM out of the water. And its transit system? Where do I begin?! For one thing: IT WORKS. Well. Consistently. Seriously, the TMB rarely if ever trends on Twitter as a hashtag fail.

Dislike the comparison to a European city, Toronto? Think it’s akin to comparing Valencia oranges to McIntosh apples? Fine. Let me draw your attention to another city on this side of the pond: Chicago.

Also on a large body of water—a Great Lake no less! Comprising around 8 million people—granted a little larger than either you or Barcelona, but fundamentally in the same class. And what of their high culture and professional athletics? IN SPADES. Not to mention a zoo and an effing aquarium.

Chicago also has a habit of electing civic leaders with, say, vision and, ah, competence. (See Daly, Richard M. v. Lastman, Mel; Emmanuel, Rahm v. Ford, Rob.) And don’t you go holding up your David Miller, Toronto, as proof you’re not completely hopeless when given the chance to install someone in the mayor’s chair with something approaching a brain. Having experienced both Lastman and Miller, you then opted for Ford—IN DROVES.

Yep, you seem to struggle—and struggle mightily—with the evidently impossible task of sound civic planning. When faced with what to do with your spectacular coastline, for example, you opted for the Gardiner Expressway. Chicago? Grant, Millennium and Lincoln Parks, Shedd Aquarium, Adler Planetarium, The Art Institute of Chicago, Soldier Field, Jay Pritzker Pavilion, Navy Pier

Enough said.

Granted, you’ve still got the CN Tower. Be proud of that. Honest. A shame, however, it’s situated next to that billion-dollar white elephant, the SkyDome—sold to Rogers Communications for the tidy sum of $25 million. I mean, Jesus Christ. Even Montreal, with its decrepit Olympic Stadium, can take pride in the fact its billion-dollar engineering ignominy oozes (or at least crumbles) retro-futuristic cool.

Speaking of the Olympics, nothing tops the hubris of frequently floating yourself as a candidate for them. It’s laughable. You haven’t even properly connected your airport with your public transit system; in contrast, London has dozens to its THREE major international airports and it’s still working on contingency plans to move people about.

And when last invited to host something of any international import—the G8-G20 Summit—your police force—like a newbie tagging along with Charlie Sheen on a 48-hour hooker-and-blow bender—lost its shit in orgiastic displays of Orwellian oversight and Draconian enforcement. Imagine, as London (no stranger to serious and devastating acts of terror) must do now, having to actually implement the far more robust, lengthy and sophisticated security measures necessary to safeguard an event even remotely close to the Olympics, let alone the Olympics themselves.

Get real.

No, seriously. Drop the bullshit. Either you accept things as they actually are and resign yourself to simply being the biggest Canadian fish in the world’s municipal ocean, or you buck up and set about bridging the gap between how you see yourself and how the rest of the world actually sees you.

The choice is yours. Choose wisely.

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What a weekend!

As I already mentioned, I made a quick trip to Chicago to attend a friend’s wedding this weekend. And even the fact I went straight to work from the airport upon returning to Winnipeg, hangover still lingering in my head, didn’t diminish the sheer delightfulness of it all.

What wasn’t to like about the past 36 hours?

Great food.

As always, Chi-town didn’t disappoint: a fantastic rehearsal dinner at Joe’s Seafood, Prime Steak and Snow Crab; a quick breakfast at Rick Bayless’ fantastic short-order Mexican joint, XOCO; a surprisingly wicked Moroccan lamb burger at Sable; and, best of all, an absolutely stunning dinner at the wedding itself.

Great weather.

Sure it was hot and humid and the risk of showers ever present, but, for a better part of the day on Saturday, we were able to take in the sights and sounds of the Magnificent Mile and the even more magnificent Millennium Park without a drop.

Heck, I even managed to squeeze in a quick visit to the Art Institute and, along the way, glimpsed Seward Johnson’s latest sculpture along Michigan Avenue.

Great times with old friends.

The best part of all.

On the heels of nine straight days working, I find myself sitting in the international departures lounge of Winnipeg’s James Armstrong Richardson International Airport.

No, I’m not fleeing the country for a non-extraditing South American refuge. I’m off to Chicago for a friend’s wedding. And by my count, I’ll be in the city — and what a city! — for no more than 36 hours.

Jaunt, indeed!

I’ve been to Chicago before. It’s a first-rate city and one of my favourites. Sadly, my tight schedule means I’ll have less time to sample the city’s remarkable culinary delights than I would have liked. (Alinea continues to elude me. Grumble.) Still, I’m hopeful I’ll have enough time to squeeze in a quick visit to the city’s eponymous Art Institute.

More to the point, and more importantly, I’m incredibly excited to witness my dear friend’s nuptials.

Chicago, here I come.