TORONTO — When Ana Bailao joined Toronto city council in 2010, the affordable housing committee chair was considered a low-profile appointment, a losing file for those seeking political star power.
The committee met infrequently and struggled to garner wider public attention. But it was a file then-rookie councillor Bailao was eager to take on, seeing it as an opportunity to make a difference.
“I always knew that this is an area that I wanted, because I always felt this is so foundational,” she said in a recent interview.
As the issue rose in prominence, so too did Bailao’s political profile, eventually landing her a role as deputy mayor and housing point person to former mayor John Tory.
Now, the 46-year-old is staking her campaign to replace Tory in large part on her housing record. She has positioned herself as a pragmatic consensus builder — backed by seven city councillors and nine Liberal parliamentarians — who helped elevate affordable housing from a political afterthought into a defining issue of the June 26 byelection.
But as Toronto grows increasingly unaffordable and record numbers of people go unhoused, can she shake her critics’ label as the maintainer of a broken status quo?
Bailao immigrated from Portugal at age 15 with her sister and parents, sharing a one-bedroom apartment near Brock Avenue and DundasStreet, in a neighbourhood she would later represent on council. Bailao, the daughter of a construction worker and a seamstress, saw herself becoming a social worker, but was recruited to work in city councillor Mario Silva’s office during the last year of her undergraduate degree at the University of Toronto.
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When Silva left for federal politics in 2003, then-28-year-old Bailao ran for his open seat and lost. After a stint in the private sector, she ran again and won in 2010.
“This is what I love. It’s the city, it’s the issues, it’s how you work with the communities, how you shape the community. And it has such a huge impact in people’s lives,” she said, sitting in a park behind the Art Gallery of Ontario, across from her campaign office.
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“That’s what I’m passionate about, because it’s the little things that I think have a big impact.”
One of Bailao’s most notable affordable housing victories arrived early in her first term, in 2012. She convinced the mayor to walk back a plan that would have seen Toronto Community Housing Corporation, the city’s social housing provider, sell off more than 600 units of single-family homes.
“I think that’s where Ana really shines, is that as someone who hasn’t done the grandstanding and has that reputation for being a collaborator,” said Braden Root-McCaig, her chief of staff at the time, and now her mayoral campaign’s policy director.
The victory was sealed almost a decade later, when she helped negotiate the transfer of TCHC’s single-family housing portfolio to two community land trusts.
Over the course of that decade, Bailao spearheaded a number of affordable housing projects, such as a 10-year housing action plan. She helped develop a fund for community housing providers to purchase and preserve affordable units. She took a leadership role in supporting the approval of laneway and garden suites.
She gained the respect of some city councillors who did not always vote with her and Tory.
“I have seen her in the mayor’s boardroom doing the moving along of things that the mayor has to do even though she wasn’t the mayor,” said Coun. Shelley Carroll, a 20-year council veteran who gave the campaign an early endorsement.
Bailao’s record, however, is not without its critics. She failed to get the votes needed to legalize rooming houses citywide while housing chair, in what she calls the biggest regret of her tenure. Her critics have questioned her decision to fundraise from developers. She defended the police budget against attempts to reallocate $10 million to rent supplements and voted against a motion to freeze transit fares.
And while Bailao helped establish a housing-first pilot program for a homeless encampment in 2021, known as the Dufferin Grove model, she has been accused by frontline advocates of overstating her part in its design and for not standing up against encampment evictions earlier that summer.
“I think in regard to that, it was politically expedient for her to change the approach,” said Diana Chan McNally, a longtime advocate for the homeless.
Underlining Bailao’s final term on council is a record of voting with Tory more than 90 per cent of the time.
“I think she had the opportunity, if she’s truly progressive, to push harder. And I didn’t see that happening. I think what we saw instead was, for the most part, upholding the status quo,” Chan McNally said.
Bailao opted not to seek re-election as a city councillor in 2022 and took a job with a large Toronto developer as its head of affordable housing and public affairs. With Tory seeking a third term, her plan was to build affordable housing, then run for mayor “at the appropriate time,” she said.
That time came sooner than expected, when Tory admitted to having an affair with a staffer and resigned in February.
Her campaign has inherited some of the personnel and policies of Tory’s administration, including a promise to keep taxes at or below the rate of inflation despite a nearly $1-billion budget shortfall.
But what she has not inherited from her former boss, according to polls, is his popularity. Bailao has polled in the low teens for most of the byelection campaign, trailing front-runner Olivia Chow by around 20 points.
Pollsters and her campaign have suggested part of the problem, especially in a 12-week byelection campaign, is that her name recognition does not measure up with Chow, a longtime NDP parliamentarian, or ex-police chief Mark Saunders.
But it’s never been her style to seek out the spotlight, she said,going back to her decision to take on the affordable housing file.
“I don’t need to be recognized on the street,” she said. “It’s not about me. It’s about getting the issues fixed.”
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