In the summer of 2021, with Toronto in the grip of both the pandemic and an increasingly catastrophic housing crisis, city officials began telling the hundreds of people that had found a semblance of refuge in its public parks to get out immediately. They did it in Lamport Stadium, in Alexandra Park, in Trinity-Bellwoods. To make their message abundantly clear, they sent in hundreds of riot police, horses, and security guards, most of whom did not take kindly to the rapidly assembled community members who showed up to protect the people they often referred to as their “neighbours in tents.” Cops assaulted, kettled, and pepper-sprayed protestors, tore up tents, trashed personal belongings. Unhoused residents scattered—some to shelters and shelter hotels, others to the couches and floors of friends’ apartments, still others to less visible encampments in ravines and under the Gardiner.

A fair number of people, however, made their way a bit further north to Dufferin Grove Park. Across the street from the Dufferin Mall, Dufferin Grove was beloved for its sun-dappled playground, farmers’ market, and weekly community meals. It was also located in Davenport, Ward 9, whose councillor at the time was Ana Bailão. By that point, Bailão had been on council for eleven years, where she had spent much of her time specifically on affordable housing. She got laneway housing and garden suites approved, developed CreateTO, an agency to build affordable housing on city-owned lands, and spearheaded the city’s ambitious ten-year housing action plan, which launched in 2020. She became Mayor John Tory’s so-called housing czar, and in her last term, was Deputy Mayor for housing and Chair of the Planning and Housing Committee.

But some progressives and activists felt Bailão hadn’t done enough, or that she hadn’t pushed her boss to do enough. To them, the encampments themselves were proof of that failure, and the City’s violent response a blunt admission of dysfunction and paralysis. All over North America, housing had become an impossibly complicated puzzle, but Toronto, with its outdated zoning laws, overheated real estate market, and low property taxes, was a more confounding puzzle than most. In the summer of 2021, the average Toronto home sold for $1,089,536, and it cost, on average, $17,172 a year to rent a one-bedroom apartment, prices far beyond the average household. There were almost 80,000 households on the waiting list for social housing. That year, 216 unhoused people died in the city, 72 more than the previous year.

In Bailão’s telling, she’s been preoccupied with where, and how, people live from the moment she set foot in Canada. In 1992, when she was 15, her parents—Beatriz and José, a seamstress and mechanic respectively—emigrated from Portugal to Toronto, settling at Dundas and Brock. The move wasn’t easy—Bailão didn’t speak English, she was leaving behind friends and a beloved grandmother, and her parents had to work long hours to make ends meet. (In Toronto, José also moved into construction.) She attended West Toronto Collegiate and for a couple years, a typical day meant school, then taking her younger sister, Sara, home, and joining Beatriz to clean offices from 5:30 til 9:30, followed by homework.

The family rented at first, then bought their first house three years later. For the teenaged, earnest Bailão, who dreamed of one day becoming a social worker, that starter home meant both safety and opportunity. “It was the most powerful feeling I ever felt,” she told me. “That everything was going to be okay. That this was a city that worked.”

Bailão studied sociology at U of T, and, while at school, became involved in community organizing. Her work soon caught the attention of city councillor Mario Silva, who persuaded her to become his executive assistant while she completed her degree. That ended up being a five-year gig, with Bailão helping out on various fronts: working with residents’ associations, park improvements, transportation, day cares. She adored what she calls “the city stuff,” and, in 2003, when Silva ran federally for the Liberals, she stayed put, deciding to run as a councillor herself. She was 27, had been in the country for just over a decade, and at her first meet-the-candidates event, she trembled violently, embarrassed by her accent and deathly afraid that she would misspeak. She lost to TTC chair Adam Giambrone by 1,200 votes.

In 2010, after stints in banking and healthcare I.T. marketing, and also serving as president of the Working Women Community Centre, she ran again, and won. Her path to City Hall was different than that of her colleagues—she hadn’t been a school trustee, for instance, nor did she have much in the way of name recognition. She was also elected in the same term that Rob Ford became mayor—akin perhaps to getting your first ship crew job aboard the Titanic. But Bailão found common purpose with a small group of rookie councillors that included Josh Colle, Mary-Margaret McMahon, and Josh Matlow, and who were dubbed, depending on your perspective, “The Mushy Middle” or “The Mighty Middle.” Some considered them too deferential to Ford—killing off the Jarvis bike lane, for example—but they also pulled off budget coups, stifled Ford’s plan for a subway to Scarborough, and largely avoided the political polarization that often paralyzed council. “To keep your backbone and stand for certain things was really hard in that term,” said Councillor Shelley Carroll, “and I watched her do it.”

By all accounts, the thing that Bailão stood up for most often was affordable housing. It was a quixotic choice for a new councillor. For one thing, housing is a dizzyingly complex issue, involving all levels of government, thickets of regulation, fractious stakeholders, tricky math. The affordable housing committee, of which she was chair, wasn’t even a standing committee at the time, but more of a subcommittee that met just four times a year. The budget was $96 million. She was told that no one cared, on council or otherwise, and that to even mention the issue in campaign literature could cost you votes. But Bailão was convinced that the city’s lifeblood was in its housing and that its shape, affordability, and accessibility was entirely foundational. “It’s key for the social and economic health of the city,” Bailão said. “If we can’t have people, and especially workers, able to afford to live in the city, then what are you left with?”

For all of Bailão’s accomplishments on housing, over two terms on council, she was, from the public’s perspective, elusive. In an era of chest-thumping, egoic male politicians like the Fords and Trump (and even Tory, in his officious way), her brand of modest, strategic governance rarely registered—for better or worse. When I first started researching this story, and though I’ve lived in her ward for many years, I knew little about her. While she certainly was an improvement over Cesar Palacio, the councillor she replaced after Doug Ford cut Toronto’s wards in half in 2018 and Palacio withdrew from the election, the bar that Palacio set was embarrassingly low. I never saw her, had no contact with her or her office, had no sense of her as a person or even as a politician. I had only the vaguest awareness of her work on housing. By the end of her last term, I could only confidently say that I knew two things about Bailão really—that it took her about three years to get a badly needed traffic light installed near our house and that, during her first term, she was arrested for drunk driving after an evening spent with casino lobbyists.

And yet, like a lot of so-called progressives, I still had the impression that she was a Tory toady, as preoccupied with power as he seemed to be. Her council voting record suggested as much. She voted with Tory 87.5 percent of the time, and almost 100 percent in her last term. She voted down attempts to raise residential property taxes or reduce the police budget, even when her constituents asked her to. She appeared to be too cozy with developers, having taken a job with one when she left office, and now her campaign office was even in a building owned by that developer. She hired Nick Kouvalis, the much-reviled campaign strategist who had helped elect Doug Ford and Tory, to be her pollster. When she began to unveil her platform, promising to repair crippled services and close the city’s enormous budget gap, a number of people pointed out that it was her very government that led to those problems in the first place. As soon as the campaign began, an anonymous account called BailãoBrokeIt popped up on Twitter. When I told a friend of mine that I was writing this profile, she threw up her hands and snapped, “I can’t even with Ana Bailão.”

One person’s right-wing functionary is another’s left-wing kook. On Twitter—small sample size, granted—former Sun columnist Sue-Ann Levy opined that Bailão was a “complete puppet for the unions” while individual members of LiUNA and CUPE complained that their leaders were endorsing her. (Five labour unions have now endorsed Bailão, as have sitting councillors like Shelley Carroll, Paul Ainslie, and Chris Moise, as well as former mayors Art Eggleton and Barbara Hall.)

But the Bailão I first met in late March was neither functionary nor kook. We met at Café Paradise at Bloor and Dovercourt, a stone’s throw from the modest semi she shares with her 12-year-old Maltese poodle, Minda. She wore glasses with heavy black frames, an electric-blue blazer, and a toothy, hopeful smile. Officially, the campaign was still a few days away, but she was already in election mode. Her Twitter feed was a steady stream of commemorations—of Nowruz, of Ramadan, of Trans Day of Visibility—and teasing glimpses of her platform: promises to finally bring cell phone service to the TTC, and to upload the Gardiner/DVP to the province. At that moment, her living room was serving as her campaign office, and it was just her, her comms person Blue Knox, and a handful of volunteers.

We spoke for about half an hour. She was cordial, wonkish, understated. Still, after all these years, slightly concerned that she might say the wrong thing, she stuck to her script. At that point anyway, she was hesitant to discuss much of her platform beyond saying that she wouldn’t raise property taxes above the rate of inflation. Instead, as she had done publicly already, and would do frequently throughout the campaign, she insisted that she would get the federal and provincial governments to cough up a lot more money for Toronto. Her argument was familiar—Toronto’s the economic engine of the country, it contributes a lot more in tax revenue than other places, and it disproportionately bears the cost of infrastructure that other regions use. It absolutely needs other levels of government to invest in it. “What we need is not a cheque at the end of the year,” she said. “What we need is a fair deal. What they need to understand is there’s a lot on our books that’s the responsibility of the province and the feds.”

It was a drum that many previous Toronto mayors, including Tory, have beaten, with little to show for it. The province had already said it wouldn’t upload the Gardiner. How would Bailão do it? She didn’t strike me as an especially persuasive, seductive, or tough-nosed negotiator. Did she have a better relationship with Justin Trudeau or Doug Ford than Tory? Bailão didn’t really answer that question, but she did tell me the same story about the TCHC scattered homes that Joy Connelly told me, where she talked Rob Ford out of his plan and eventually got Trudeau to cover the costs. “I’ve done it before,” she said.

We had similar conversations in our next few meetings, where she was resolutely on-message. I wasn’t completely convinced, but as I spoke with more housing experts, a more compelling and complex figure began to emerge. Then, out canvassing with her one mild spring evening, I saw a much different Bailão. Granted, we were more or less in her backyard, doing the blocks immediately east of her house, but she displayed an ease, joy, and warmth I hadn’t yet seen. Wearing a charcoal grey pantsuit and the most sensible footwear imaginable—a cross between a tasselled, taupe golf shoe and something orthopedic—she bobbed through the neighbourhood, making small talk in Portuguese to aged homeowners and, at one door, happily getting into the weeds on the subject of short-term rentals. People in passing cars yelled out their support, others introduced her to their puppies. Early in the door-knocking, a woman named Gurbeen Bhasin showed up. Bhasin is the founder and executive director of Aangen, a not-for-profit social enterprise focused on food security and equal opportunity employment. When Bailão was a councillor, she helped Aangen fund and build a kitchen from which they produce dehydrated meals that they now sell. Bailão put her arm around Bhasin, and they walked and talked in low tones for a few blocks.

She was in top form. Her familiarity with the community, her comfort in and understanding of it, were obvious. “This is the part I really like,” she said of the canvassing. “It energizes me.” It was the kind of bland, self-flattering line a million politicians have uttered a million times. But, following her around for an hour, I found myself believing it. Or at least believing that she believed it.