Can Olivia Chow Fix Toronto? 

It’s early July, and Olivia Chow, the City of Toronto’s boundary-breaking mayor-elect, is sitting across from me in a nondescript boardroom at City Hall. She’s in one of her trademark brightly hued blazers (this one is yellow), a travel mug of black coffee close at hand. The 66-year-old will officially be sworn in the following week, so we’re meeting in an ad hoc suite of offices on the fifth floor, a temporary space where her team is planning her transition to mayor.

It’s a busy time, and not just because Chow is starting a massive new job. She has a real mess to clean up in Toronto. The city faces a budget shortfall of $395 million, housing is increasingly unaffordable, public transit is unreliable and public safety remains a major concern. In electing Chow, Torontonians have signalled a desire for change after the last two conservative (and scandal-plagued) mayors, Rob Ford and John Tory. Her first order of business: to prove she’s up to the task—especially after losing to Tory the last time she ran for mayor back in 2014. But this, I quickly learn, is exactly the kind of challenge Chow relishes.

I ask Chow why she decided to enter politics in the first place. After one of her hallmark winding answers, which starts with her plans to become an artist (she earned a diploma from what was then the Ontario College of Art and upgraded it to an honours degree in fine arts at the University of Guelph after an older cousin bribed her with a used red Fiat) and touches on her early career (her sculptures were too big to take on public transit, which is why she needed the car), Chow lands on her entry point into the political sphere: learning about the so-called “boat people” who were seeking asylum in Canada from Southeast Asia. It was 1979, and Chow was horrified to hear about people, especially women, who were trying to flee Vietnam, Cambodia and Laos.

“These women were being drowned at sea and raped in refugee camps, and there were pilots who were robbing them,” she says. “I thought Canada should welcome them. So I went to a rally and volunteered to be part of a campaign [called].”

Operation Lifeline, established by student activist turned philosophy prof Howard Adelman, worked; that year, thousands of Canadians volunteered to sponsor newcomers so they could resettle in Canada. The Canadian government also announced it would accept 50,000 new refugees by the end of 1980, eventually increasing that number to 60,000. “I thought, ‘Oh. This is what politics can do,’” Chow says.

A hopeful but deeply pragmatic person who likes to solve problems, Chow was hooked. Her art fell to the wayside. She began working at Toronto’s WoodGreen Community Services as a counsellor, teaching newcomers English. Eventually, she gained enough of a reputation as a community organizer that then federal NDP immigration critic Dan Heap hired her as a constituent assistant. Chow eventually realized she could be a politician herself. In the mid ’80s, she ran for Toronto school board trustee and won, kicking off a decades-long political career.

The Coles Notes version: She was a trustee from 1985 to 1991. After the 1985 murder of librarian Kenneth Zeller, a gay man who was beaten to death by five students in Toronto’s High Park, she advocated for adding anti-homophobia teaching to school curricula and implementing anti-discrimination policies and training for teachers. (Her trustee years are also when she met her husband, Jack Layton. The pair were married for 23 years before his death in 2011.) Chow went on to serve as a city councillor from 1991 to 2005, fighting for programs that still exist today, including providing free dental care and meals to kids experiencing poverty.

In 2006, she was elected as an NDP Member of Parliament for Toronto’s Trinity-Spadina riding. As an MP, her approach remained much the same: Frustrated by the issues that made her constituents’ lives harder, she wanted to do something about it. “That gets me into doing something to change it, then it becomes political,” she says.

As an MP, Chow joined Layton in the NDP. The pair’s marriage became a part of Canadian political history. (A statue of Layton at Toronto’s Ferry Terminal depicts the late politician on a tandem bike—a wedding gift the couple would regularly ride around the city.) She also became part of a large, close family. When Layton’s daughter, Sarah, gave birth to her first daughter, Beatrice, Chow became “Grandma Oli.” She was in the room when Sarah’s second daughter, Solace, was born. She now has four grandchildren, including two—Phoebe and Chloe—who adorably knocked on doors to support her this past summer. Also part of the family: a long-haired cat named Mauie, who rules the household and whose name means “little cat” in Cantonese.

In 2014, nearly three years after Layton’s death, Chow had reached a crossroads. When polling found she enjoyed strong support among Toronto voters, she resigned her federal seat to run for mayor. Despite her early popularity, she came in third. The following year, she lost her attempt to reclaim her Trinity-Spadina seat. For the first time in 30 years, Chow had to think about what she would do if she weren’t a politician.

“Being in the limelight is not a big deal for me at all. I just want to get things done for people.”

As it turned out, she could still use her political experience. After losing the 2014 mayoral election, Chow contacted Harvard University professor Marshall Ganz, an expert in political organizing and the architect of former U.S. president Barack Obama’s wildly successful 2008 presidential campaign. “The best teacher is failure,” he told her.

It wasn’t what she expected to hear—she was feeling pretty down, she admits—but Ganz followed the platitude with an invitation to Harvard to learn his method of community organizing. Chow’s parents were both educators, and she taught on the side for decades, first at WoodGreen and then as an instructor in George Brown College’s Assaulted Women’s and Children’s Counsellor/Advocate Program. The idea piqued her interest.

“Being in the limelight is not a big deal for me at all. I just want to get things done for people, and if I can get things done helping people learn how to organize, it’s just as good,” she says. “That’s when I pivoted to teaching.”

She returned to Toronto from Harvard in 2016 and founded the Institute for Change Leaders (ICL) at Toronto Metropolitan University, teaching grassroots organizers the skills they need to best effect change. She points to a group of child care workers who took part in ICL training as a particularly gratifying success story. “[They] persuaded the federal government to make a national early-learning and child care plan of $30 billion,” Chow says. “We were in a Zoom meeting watching the [2021] budget, and when we heard that, there were no dry eyes.”

But Chow wasn’t just teaching during this time; she was also learning. “I learned that building relationships means building power. I learned that we need to trust each other in order to accomplish anything,” she says. “And I learned to trust my own voice.”

That’s the key difference between her latest mayoral campaign and the one she ran in 2014. In a recent profile in The Local, Chow said she believes she lost back then because she was “too scripted, too nervous about her English, afraid and inauthentic.” After spending nearly seven years training young leaders, she is visibly more confident telling her own stories, even the ones that require great vulnerability to share. On the campaign trail, she talked about the abuse her mother suffered at the hands of her father—and about still loving him and committing to taking care of him in his senior years. In a perhaps surprising move for a politician, she doesn’t shy away from complicated topics or worry that they might be weaponized against her, even though she’s often a target for racist, misogynist abuse.

This is something she credits to Ganz’s training, too. “A big part of it is asking: What is that challenge in your life that [forced] to make a choice? And what does that [choice] say about your values? That got me thinking through what really shaped my earlier years,” she says. “I realized it was watching my mom be a very strong woman who was still trapped in the cultural norm that men can beat the crap out of you and you stay with that man. But our economic means made it hard to escape. Understanding that, confronting it— that makes you feel a lot more confident. This is why I do what I do.”

In many ways, Chow is a very different mayor than Toronto is used to. She’s the first racialized person and only the third woman to lead Canada’s largest city. She’s an immigrant who arrived in Canada from Hong Kong at the age of 13. She rides her bike everywhere. And she’s long been a progressive thorn in many politicians’ sides. But Chow is leading with hope—because she believes Torontonians want change and voted for it.

“I ride my bike to work, so people talk to me when I stop at red lights. Usually they start with ‘congratulations,’ but the next line that people say is, ‘I’m here to help,’” she says. “I say, ‘Wow, thank you. Let’s do it.’ I’m looking for ways to engage people who have ideas and who want to contribute or volunteer...to transform the city into a better place for everyone.”

That’s not just because she wants them to feel included. She also believes leveraging community is the only real way to make sustainable change.

Ask her long-time friends, like political strategist Bob Gallagher, and they’ll say this combination of optimism and pragmatism is pure Chow. Gallagher has known her both professionally and personally since the ’80s and considers Chow one of his best friends. “For Olivia, optimism is not just a defence mechanism; it’s also part of her modus operandi,” he says. “She paints a picture of the future, of what can be done, and gets people to look at that.”

This optimism extends to her downtime, too. A nature lover who goes camping regularly throughout the summer, Chow also happily spends time outdoors into the fall and winter. According to her friend Tania Liu, “she does everything to the fullest.” That includes going hiking, paddle boarding and backcountry camping with Liu, sometimes accompanied by Liu’s husky mix, Mispun.

“There are different types of friends: people who will just listen to your complaints, people who will take you out for food or drinks,” Liu says. “Olivia is always thinking of a solution for you.”

As she embarks on her tenure as mayor, Chow is approaching her duties just like she did every other political—and personal—challenge she’s faced: She sees things that need fixing and looks for a way to make that happen. It’s perhaps the most common refrain from her entire political career. “[There] always something that’s not right [that] someone needs to [fix],” she says. “It might as well be me.”