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When I arrive at Amber Morley’s constituency office in west-end Toronto – a small room tucked into the front of the housing co-op where she grew up and still lives – she’s in the middle of watching a city council debate on YouTube. This may seem like penance for the rest of us, but for a political junkie such as Ms. Morley, it’s engrossing. And enraging.

“I find it very frustrating,” she says, shaking her head. “Why aren’t we moving ahead with the important files in the city?” The files she’d like to advance, if she is elected councillor in Toronto’s Ward 6 in the October municipal election, include affordable housing, transportation and giving young people voices and jobs.

Another thing Ms. Morley notices when she watches city council debates: There are not many faces that look like hers. She is biracial – her dad is black, her mom is white – and she’s 29 years old. She is not the product of wealth, or a political dynasty. She is, however, a product of a program called Women Win TO, which aims to change the monolithic face of city council this fall, by giving women from non-traditional backgrounds the skills and support to run for office.

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ILLUSTRATION BY HANNA BARCZYK

”City hall needs a breath of fresh air,” Ms. Morley says, sitting in front of a white board that divides up her ward’s challenges by neighbourhood: road safety, development, lot-splitting, bike-sharing, a light rapid transit system to connect the fast-growing suburb to the downtown. There is a lack of affordable housing across the ward, as there is across the city; at the community centre where Ms. Morley volunteered for years, homeless people are sleeping on the lawn.

Ms. Morley already had political experience – she’d worked as an assistant in two Toronto councillors’ offices – but, like most people who grew up outside the networks of power, needed guidance and coaching on how precisely to run a campaign. What’s the best way to raise funds? How do you assemble a campaign team? Where do you meet the key stakeholders in your district?

All those lessons were part of the curriculum at Women Win TO, which began in May, 2017, like a boot camp for political newbies. Every month, the prospective candidates met with experts to talk about the particular challenges they faced while running from outside traditional networks of business and politics.

Women Win TO was co-founded by Hema Vyas, who’d unsuccessfully run for council in 2010, as a way to counter the monochrome leadership of a city that is profoundly multicultural (visible minorities make up 51 per cent of the city’s population.)

“When you look at city council, it’s less than a third women, and there’s one woman of colour, Councillor [Kristyn] Wong-Tam,” Ms. Vyas says when I sit down with her. “Every time, I say that it’s stunning and frankly shameful.” So she set out to recruit women from non-traditional political backgrounds who wanted to run on a progressive agenda, and gave them practical advice about how to organize a campaign. The first graduating class of Women Win TO has already been a success: Of 15 women in the program, two were just elected to the Ontario Legislature (Jill Andrew and Suze Morrison) and six are running for city council.

The day before I met with Ms. Morley, there was a political earthquake south of the border. Alexandria Ocasio-Cortez, a 28-year-old New York Democrat with little political experience and an unashamedly progressive platform, had defeated a 10-term male incumbent to win the party’s nomination for the November midterm Congressional race.

Ms. Morley watched Ms. Ocasio-Cortez, and it was a bit like looking in the mirror: They were both in their 20s, former bartenders, outsiders running on progressive platforms with shoestring budgets against long-entrenched incumbents (the councillor in Ms. Morley’s ward was first elected in 2003).

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As Ms. Morley says, “Her passion for community and community-centred policies are 100 per cent in line with what I’m trying to bring to the table. It’s so encouraging that people are ready for that message and that kind of leadership.’’

Across the city, someone else sees herself reflected in Ms. Ocasio-Cortez’s win. Saron Gebresellassi is 31, a lawyer who speaks seven languages, and she’s taken on a challenge that rivals the New York Democrat’s: She is campaigning to unseat the well-heeled, well-connected incumbent, John Tory as mayor of Toronto.

‘’Her win was so inspiring,” Ms. Gebresellassi says. “She pulled off a major political upset. And she’s my age, from an immigrant background, a working-class background, with no electoral experience. I thought, ‘Well, we can do it, too. We can give it a fighting chance.’’’

I met with Ms. Gebresellassi on the campus of Ryerson University, where she got her first degree in Radio and Television Arts (she also has a masters in education as well as a law degree.) She, too, comes from outside the sphere of political influence: Her parents were refugees from Eritrea, and Ms. Gebresellassi grew up in Toronto Community Housing in one of the poorer corners of the city. When she went back there to knock on doors, one of the kids in the neighbourhood said, “I didn’t think we were allowed to run for mayor.”

Ms. Gebresellassi put her law career on hold, joined the Women Win TO program and decided that the best place for her progressive vision was on the mayoral ticket. She thinks the budget for policing is too large, and wants to see youth crime tackled through earlier interventions such as job creation and mental-health services. She wants to see transit fares frozen, and would ideally like to see a free public-transit system.

It is a Herculean task, no doubt. These women, and others like them, are running campaigns against long odds and the weight of history (there have been 65 mayors of Toronto, for example, and all of them have been white; two were women). But this year, with the ward boundaries redrawn and change in the air, anything is possible.

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As Ms. Gebresellassi says, she wouldn’t be running if she didn’t think she could mobilize voters who also feel shut out of power structures. ‘’Is it an uphill battle? Absolutely. Is it trying to achieve the impossible? Possibly. But it’s not going to take another hundred years to elect a racialized mayor, or a progressive mayor. It just takes courage.”

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