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Joe Cressy is the NDP’s candidate for the federal riding of Trinity-Spadina.

From the glass towers of the waterfront to the hipster enclave of Liberty Village, the burgeoning southern portion of Toronto's Trinity-Spadina riding is a political wildcard that could prove to be the difference in the upcoming by-election.

This one of the youngest neighbourhoods in the country. The sidewalks hum in early evenings with a parade of multicultural professionals. They're creative types with sunglasses, beards and yoga mats tucked under toned triceps. Children and the elderly are rarer sights. It's a condo land, running south of Queen Street to the lake shore, from Yonge St. to Dufferin St. – and with new towers rising all the time its political character is still under construction.

The south will not only play an important role this time, but also in the 2015 general election when it is re-born as a riding in its own right, Spadina-Fort York.

Roughly 90 per cent of the 65,000 people here live in high-rises. More than 55 per cent live alone, twice the Canadian average. Three quarters of all households are led by someone younger than 45, and the average household income of $113,000 is well above the national level (figures from Environics Analytics enhanced census data).

Young, wealthy, living alone in a tower, they could be mistaken for characters in a fairy tale. They're unlikely to vote for Stephen Harper, but the task before them is to decide whether the Liberals or NDP are best placed to claim his throne.

The federal by-election pits a relatively young candidate in Joe Cressy of the NDP against a high-profile Liberal city councillor in Adam Vaughan. Mr. Cressy inherits a massive 20,000-vote, 30-percentage-point margin from his predecessor and former boss Olivia Chow, who resigned to run for mayor. A recent Forum poll, though, placed Mr. Cressy a distant second. The NDP is putting a lot of faith in data. Identifying likely voters and getting those votes to the polls will be crucial, particularly with the June 30 voting day, a Monday, falling in the middle of what many will treat as a four-day long-weekend. Turnout will likely be very low.

On a mid-week afternoon a month before voting day more than a dozen people are at work in Mr. Cressy's campaign office. On the wall is a map of the riding divided by polls and colour-coded according to the strength of NDP support in 2011. The warmest areas of support are in Little Italy, Seaton Village, the Annex, Chinatown and Toronto Island. The coolest are in the riding's southern half, where entire neighbourhoods have risen from nowhere over the last decade.

In a dusty, windowless back room, three people are hunched over keyboards entering data from the latest canvass. The job isn't glamorous, yet it's the backbone of a local political machine. Mr. Cressy can't match his opponent for name recognition, but he's got better data, he says.

The NDP has information on 75,000 voters in the riding, he says. That's nearly three-quarters of registered voters. But what's the information worth?

"Data is gold," said Mr. Cressy. "We have data going back to the 1980s."

Later that night Mr. Cressy is going door to door in a Liberty Village condo with Todd Hofley, president of the Liberty Village Residents Association. Mr. Hofley says more than 40 new high rises have gone up in the riding since the last election. Reaching these voters is difficult. They're highly educated (57 per cent have university degrees), but they're also young (the NDP led all parties among the under-34 crowd, according to Ipsos Reid exit polling). Their high incomes would suggest they're not the most receptive audience, since support for the NDP peaked in 2011 among households earning less than $30,000. But there are other factors at play. Support for the NDP in 2011 was highest of the three parties among singles, according to Ipsos-Reid, and down here singles abound.

Before he knocks on his first door, Mr. Cressy offers a crash course in the NDP data gathering system. He flips open the voters list on his clipboard. It shows names and phone numbers of residents. Then there's a space where their politics are rated. A number one means solid, locked-in NDP support; that person will be chauffeured to the polling booth if necessary. A two is for those leaning to the NDP; they'll get a lot of attention and possibly a follow-up visit from the candidate. Three is undecided: they might get more attention, particularly if they live in areas historically favourable to the party. Four is for those who say they're voting for another party; they likely won't be contacted again.

The sheet also shows how the voters said they would vote in the 2011 federal and provincial elections. That's just the most recent data, Mr. Cressy says. The computers back at the office have more.

Mr. Cressy is breaking one of his own rules tonight. Normally NDP candidates should tackle condo buildings from the ground up. That way they hit more likely supporters first – the renters on the lower, cheaper floors.

He finds a mix of people who are engaged (they're considering the NDP or the Liberals, never the Tories, at least out loud), and those who are anxious to just close the door. Some won't open the door at all. As soon as he sees the light flicker behind the peephole, Mr. Cressy just starts in with his pitch.

"I'm Joe Cressy, I'm your local NDP candidate in the federal by-election in Trinity-Spadina. I'm coming around to 78,000 doors and trying to introduce myself," he says. The number of doors changes nearly every time (it's variously 78,000, or 70,000 or 75,000), and like many a politician before him he pays self-deprecating tribute to the walking shoes that make it all possible.

Mr. Cressy, the 29-year-old son of former city councillors Gordon Cressy and Joanne Campbell, tends to highlight his experience at the Stephen Lewis Foundation working on HIV and AIDS in Africa and on literacy in fly-in First Nations in northern Ontario. If that seems too distant he mentions the "I heart public transit" campaign he co-founded with Ms. Chow. As they stand in the carpeted hallway, with the sound of TVs and the smell of cooking leaking from within, the voters listen politely. A few say they'll go NDP, a few more say they're weighing their options. Not one raises a political issue independently, although a couple, when prompted, agree that transit is a mess, even if the national transit strategy Mr. Cressy favours doesn't roll off their tongues. Mr. Cressy invests more in talking than listening. He never asks what issues matter to them. He needs to introduce himself, he explains. Questions are for the second canvass.

"You know, more people ride the TTC every day than live in nine provinces and territories," Mr. Cressy says.

"The face of Canada is now an urban face. 80 per cent of Canadians live in urban centres." (The last part is true if one uses a very broad definition of urban centre.)

His sheets fill up with twos and threes. He shakes hands, as many as three times with the same person, even those who say they're covered in goop from cooking. Mr. Cressy says in-between door knocks that's he's conservative when it comes to marking people down as ones. "Once you're a one, we tend to back off, don't give you the hard sell," he says. Besides, no one wants to tell him face to face that they're supporting someone else. He explains that according to the party playbook his campaign will follow up by phone with everyone in this building in the coming days, since the candidate has just been through. Once they've got a better sense of how many ones and twos are in the building they'll follow up with a persuasion canvass, a team of volunteers who might offer a more targeted message. They'll also follow up with special teams that can handle those who speak Mandarin, Cantonese or other common languages.

Many residents are the children of immigrants who have moved from the suburbs to be closer to downtown. They've chosen a lifestyle where they walk, bicycle and take public transit to work at a rate far higher (66 per cent) than the car-dominated Canadian average (74 per cent commute by car). The party knows less about them and their voting habits, partly because on average they've lived here less than four years. The hope is that these newbies will conform to the broader trend in the riding. Mr. Cressy's campaign points out that while the immigrant working class areas of Little Italy and Little Portugal have seen an infusion of younger, wealthier, Anglo residents, the area's politics have remained largely pro-NDP.

At the end of the night Mr. Cressy heads back to the office. He's going to grab a drink with the volunteers. The data will be entered tomorrow. He'll keep doing this for the next 30 days, hoping that each contact makes a difference. Does the local candidate matter? A Canadian Election Study paper found it was less important than the party or leader, but it was still decisive for about 5 per cent of voters. Get their data, get their vote, get them to the polls. That's how a campaign works.

"It's a system built around identifying your core vote," Mr. Cressy says. "Your lists and your data are everything."

Joe Friesen reports on demographics from Toronto.