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Kelly: This year’s Blue Jays see a Toronto more comfortable with winning

Five months ago, as the Toronto Raptors were getting ready to face the Cleveland Cavaliers in the NBA playoffs, CBS Sports' online operation made the mistake of being reasonable.

It posted a poll asking readers which team would win the championship: Cleveland, Golden State, Oklahoma City or "Other."

Let's agree at the outset that any reasonable person who has either seen basketball played or had basketball explained to them or heard that there is a thing called 'basketball' knew that Toronto's chances of winning a basketball title were less than nil.

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But local custom in our most thin-skinned metropolis demands that Toronto be seen freaking the hell out.

Mayor John Tory wrote a gloriously self-pitying open letter, which included this gem: "We're not in the least bit offended. In fact, we're used to being underestimated."

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Yes, the biggest, shoutiest city in the country – we're a regular Little Engine That Could. They're always underestimating us up in, like, Vancouver or Montreal or … what's another city in Canada? We've forgotten the names of the others. There's the one that starts with O and the … come on, give us a hand here.

I mean, they all said we couldn't get our public-transportation situation worked out. And guess what, pal? We couldn't! Maybe that's worth an open letter.

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The useful thing about Tory's pandering fit of pique was illustrating to ourselves how we appear to everyone else. Ridiculous. Occasionally charming in a nebbishy Woody Allen-frets-about-sports sort of way, but mostly ridiculous.

Toronto's pipsqueak tendency to put up its dukes every time someone brushes past it in the international high school hallway is a function of loserdom. Not being in it. But the jarring experience of coming out of it.

When you reflect on the 20 or so years just past when Toronto was uncompetitive at every major-league sport, it was an oddly comforting time. You watched your teams without expectation. If they won, it was a pleasant surprise. When they lost, your disappointment had already been factored into the experience. Eventually, the disappointment became the experience.

There is a perverse pleasure in feeling predictably terrible about something that doesn't matter. It makes all the things that do matter, which you also feel terrible about, seem less important by comparison.

When people outside Toronto made fun of us, we didn't notice. We were too busy raging at ourselves.

Also, no one bothers to mock the sports culture of a city that is actually terrible at sports. There are no 'Ha Ha Sacramento' jokes.

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They only come for you when you've started to achieve something. When this happens, the city is never properly prepared. It's still living in the 'Nothing good can ever happen here' stage. When something good starts happening, it creates a frenzied sort of joy. You're pretty sure this is going to end any minute. Maybe it's all a trick. But you are going to crouch at one end of the sports buffet table and tip it toward your mouth. You are getting more than your fill.

Now that you've entered the so-so sports-city club, strangers will want to take you down a bit. Burgs that have been there before find this intercity banter amusing. Toronto wheels around maniacally and has a finger jammed up your nose before you've finished making the joke. Toronto can't take jokes right now. We're just a little emotional.

That was certainly the feel over the past year as the Blue Jays and Raptors enjoyed a nice performance bump. It was exacerbated by the fact that no one expected those teams to win championships. We became the guy who orders four beers at last call – trying very hard to extend a moment that is slipping away.

As Toronto returns its attention to Cleveland ahead of Friday's Game 1 of the American League Championship Series, this feels different. It's less frantic this time around.

In many ways, Cleveland is Toronto, just a little further ahead in its civic-healing process. It won that NBA championship, its first major anything in 50 years. America still loves lobbing 'I think your river's on fire' zingers its way, but the easily wounded Cleveland of 20 years ago is gone. Because you're only able to act like you've been there before when you've been there before.

This is the new Toronto's first try at that. Unlike themselves a year ago, or the Raptors in spring, this Blue Jays outfit has the low-key swagger of a team that could actually win a World Series. Nobody wants to say it out loud, but this is the chance. Given the way the Jays are currently constructed, contract-wise, and how difficult it can be to predict regular-season baseball, maybe the only realistic chance for a while.

That low hum you hear through the city today? That's everybody getting on the same wavelength as far as that's concerned. Now or (what could seem like) never.

Were that NBA poll or any other sort of meaningless, U.S.-based provocation posted today, the reaction would be different. Among reasonable sorts, there would be no outrage. A few keener minds might find it funny.

The mayor would write no letters. Public figures would feel no need to be seen being offended – the great performance art of our time.

Because Toronto has, in some important ways, grown out of it. Not grown up. But become used to things as they should be, rather than the way they always have been.

One of the many great things about sports is how they are the advance scout of culture. They forge ahead, chopping down tree branches and clearing paths into new territory. The rest of us follow slowly behind. Eventually, we catch up.

This series can be Toronto's catch-up moment. It's where the City of Perpetual and Irritable Regret has a chance to become the City That Allows Itself to Enjoy Things and Take a Joke.

In the end, making Toronto less brittle may be a bigger achievement for the local baseball team than any trophy.

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