Editors’ note Aug. 28: Trent Lee volunteered briefly for the Hollett campaign this summer, but quit all partisan involvement before pitching the series of riding profiles to which this article belongs. Our conflict of interest policy is available on our website and forbids personal or pecuniary interests in the subject of reporting. This policy does not cover past affiliations, but a disclosure should nevertheless have been added to the article.
The statement attributed to Freeland campaign manager Dana O’Born in this article was made to Mr. Lee and then verified with Ms. O’Born by one of our editors on a fact-checking call. We stand behind the reporting.

Chrystia Freeland (Liberal)

Chrystia Freeland

Alex Guibord

Career: Politician, author, editor at the Financial Times, Globe and Mail and Thomson Reuters.

Issues: Economy, infrastructure, investments, sustainable urban planning, income inequality, gender equality, job growth, Canada’s presence on global stage, rail safety along Dupont corridor.

Career Highlights: New York Times best-selling author of Plutocrats: The Rise of the New Global Super-Rich and the Fall of Everyone Else. Appeared as a guest on The Colbert Report.

Jennifer Hollett (NDP)

Jennifer Hollett

Alex Guibord

Career: CBC and CTV journalist, activist and former MuchMusic VJ.

Issues: Health care, stronger pensions, affordable child care; jobs through hiring incentives for small businesses; investment in public transit and green spaces to shorten commutes, reduce air pollution and make Toronto more liveable.

Career Highlights: Created the Super Pac App for the 2012 U.S. federal election, a smartphone app which analyzed the audio from campaign ads and paired it with data about who paid for the ad, and how truthful it was. Involved with the Leading Change Network, a grassroots group credited with aiding the success of Obama’s 2008 election campaign.

Battleground Toronto

Chrystia Freeland vs. Jennifer Hollett. It’s a showdown that should be billed as the battle of the journalists. In the Toronto riding of University-Rosedale, two distinguished women in media are vying for election in a contest that will come down to control of each candidate’s public persona.

The new riding is made up of parts of the Trinity–Spadina and Toronto Centre districts. Including the neighbourhoods of Rosedale, Yorkville, the Annex and Little Italy, the riding boasts a polar opposite dynamic in demographics.

The Annex harbours hipsters and leftist socialites, and Rosedale’s manors are where fiscally conservative Liberals traditionally reside. Not far off is Yorkville with its expensive shopping district, grocers, cafés and boutiques. Conversely, the riding also includes the University district, which is composed of mostly young urban students. It is typified by Little Italy’s strip, where Hollett’s office is located alongside small business owners, nightclubs, hipster cafes, second-run cinemas and record shops.

After spending time talking to voters in the riding while researching this story, two issues are brought up repeatedly, particularly by Annex residents: Bill C-51 and pipeline politics. These issues seem to have staying power in this long campaign, and C-51 in particular is a cause of division within Liberal ranks. On social media some have attested to cutting up Liberal membership cards and switching their votes to the NDP, many for the first time.

Key to victory: capture the grassroots

Grassroots campaigning may prove key, and Hollett is known within NDP circles as the New Democrats’ strongest mobilizer of militants. With a social-media-savvy team and an army of canvassers in the streets even before the campaign’s kick-off, Hollett’s team expects its strategy to produce results on election day.

However, Hollett will have to overcome the incumbency effect. Without any track record of holding public office, Hollett’s inexperience as a politician will likely be used against her by Liberals who will contrast it to Freeland’s three years as an MP.

Dana O’Born, Freeland’s campaign manager, spoke to Ricochet by telephone earlier this month. She said the Freeland campaign plans to run on family issues among others, and will highlight the fact that Hollett is not a mother, while Freeland is a mother of three.

This contrasts with the tack taken by another high profile Liberal candidate in downtown Toronto, Adam Vaughan, who is campaigning against the NDP’s Olivia Chow in the riding of Spadina-Fort York. Vaughan reportedly said earlier this week that the NDP’s proposal for a national child care plan didn’t resonate in his downtown riding, claiming that only eight per cent of families in his riding had children.

In the past, candidates had to rely on the credibility of their national leader and party to carry them into Parliament. But with Justin Trudeau’s popularity relegated to third-place status and the Liberals unable to break out of the twenties in national polls, Freeland may have to break out on her own and distance herself from the party leader — a difficult task given Freeland is Trudeau’s top trade advisor and is still dogged by controversy over her nomination fight against Christine Innes, who slapped Trudeau with a defamation lawsuit for shoving her out of the race, reminiscent of the Eve Adams fiasco late last month.

The bottom line

This is a high-profile matchup of Liberal and NDP star candidates, one that is hard to predict given the speed with which tectonic plates are shifting across the national political landscape. In urban Toronto the Conservatives aren’t a factor, and voters will cast their ballots with an eye to ousting Harper. What remains to be seen is if they will decide the NDP or Liberals are the better bet to achieve that objective.