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Olivia Chow, Mayor Elect for the city of Toronto, holds a press conference outside city hall on June 27.Fred Lum/The Globe and Mail

Toronto’s incoming mayor Olivia Chow will face significant hurdles when she takes office, inheriting a housing crisis, concerns about deteriorating city services and lack of money to fix the problems.

Ms. Chow, who won 37 per cent of the vote in Monday’s by-election in a field of 102 candidates, has set high expectations for herself to address these massive challenges. She pledged throughout the campaign to change how the city has been governed and improve affordability and quality of life.

Past colleagues and housing experts say Ms. Chow’s previous political experience, determination and ability to collaborate across ideological lines will help her in tackling the steep task ahead.

One of her biggest challenges after she takes office on July 12 will be implementing an ambitious housing plan. Ms. Chow’s campaign platform promised to increase the supply of housing in Toronto, which will cost a significant amount of money and require the backing of council. She will also need support from the provincial and federal governments, who in recent weeks have been telling each other to provide more money for municipalities.

Several factors outside the city’s control could affect how much housing is built, including construction costs, the labour market and interest rates.

Ms. Chow’s plan includes having the city act as a developer to build 25,000 rental units over eight years, at least 20 per cent of which would be affordable units and another 10 per cent rent geared to income units (30 per cent of household income). She also plans to create a $100-million affordable homes fund focused on stopping evictions for renovations.

Toronto’s homeless encampments are a challenge on Olivia’s Chow’s doorstep

Speaking with The Globe in a temporary office on the fifth floor of a City Hall tower two days after winning the election, Ms. Chow said “anything is on the table” to advance housing.

But that stops short of using “strong-mayor” powers granted by Premier Doug Ford’s government to override certain council decisions or pass bylaws with only one-third support of council. Ms. Chow has vowed to never use those powers.

“I will be bringing in some top people in the development industry that have many years of experience in the private sector to help. I will also bring in people who have many years of experience in a non-profit role to assist and I will be bringing in people from the government sector,” she said.

Toronto-based urban planner Sean Galbraith called Ms. Chow’s housing plan ambitious but said he has doubts about it coming to fruition because of many external factors. Ms. Chow is calling on both the provincial and federal governments to provide $14.6-million in rent supplements to help 1,000 households experiencing homelessness exit the shelter system.

“I’m just pretty skeptical that there’s going to be the political will to have the financial will,” he told The Globe. “I don’t know that there’s a good roadmap on how to get there.”

Ms. Chow called a special meeting of council’s executive committee in August – when they are typically on recess – to deal with pressing matters including the city’s long-term financial plan. Toronto is facing a budget shortfall of roughly $1.5-billion this year and last year. A report on the long-term finances projects a deficit of nearly $50-billion over the next 10 years.

Ms. Chow has had a lengthy political career to get to this point. She started out being elected as a school trustee in 1985 and then served as a city councillor for more than 13 years before making the leap to federal politics as a member of the NDP.

She has also spoken and written about the adversity she faced in her early life, including writing a memoir about her journey to Toronto from Hong Kong at the age of 13. Her family struggled to get by and her father was abusive toward her mother. Ms. Chow’s husband and long-time political ally Jack Layton died in 2011.

Ms. Chow then lost two successive elections, an attempt to become mayor in 2014 and a bid to rejoin the federal political scene a year later.

“Though I’ve been knocked down a few times over the years just like you, I always got back up,” Ms. Chow told supporters during her victory speech Monday night.

Her victory indicates the scope of her comeback, and belies her downtown roots. She won handily in a number of wards far from the city centre, including five in Scarborough that former mayor John Tory won last fall. She also edged runner-up Ana Bailão in Willowdale, a north Toronto seat that is held provincially by a Progressive Conservative and federally by a Liberal.

Ms. Chow told The Globe she believes she’s the right leader to bring residents together and inspire them to build a better Toronto. She is the first person of colour elected as mayor of Toronto, where more than half of residents identify as visible minorities.

“As the mayor that reflects more than 50 per cent of people that live in the city because of where I came from, it’s also a signal to the people that traditionally don’t see themselves at City Hall that they can participate. Their ideas work. We need them to be involved and yes they do have the power to do so,” she said.

Former municipal councillor Joe Mihevc sat beside Ms. Chow for eight years at city hall, and remembers her ability to work with people to find “the island of agreement.”

“She will not present as an alpha hierarchical leader,” said Mr. Mihevc. He praised Ms. Chow for having “supreme” negotiating and mediating skills, adding: “so all this stuff of, oh, she’ll never be able to work with Ford and never be able to work with the right side of council, it’s just not accurate.”

He noted that during her time on council she was able to work with right-wingers such as Case Ootes and Rob Ford, the late brother of the Premier. Another right-winger, former mayor Mel Lastman, appointed her the city’s first children and youth advocate. In that role, she worked to nearly quadruple a school nutrition program and provide free dental care for children of low-income parents.

Former mayor David Miller, who overlapped with Ms. Chow for the first part of his administration, said that her win speaks to a new dynamic emerging in Toronto politics. He pointed to last fall’s municipal election, in which six racialized councillors were added to what for years had been a largely white body.

“That’s where the future of council is, and that’s the coalition that Olivia put together,” he said. “That’s where Toronto is going. You know, it’s been a Tory town for a long time but its diversity is going to change the nature of the political discourse at city hall, and she’s captured that coalition and it’s a really powerful base for her and one of the reasons why she’ll be able to be strong.”

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