the Pragmatist

Ana Bailão has built a political career on collaboration and consensus. But can the progressive centrist inspire a city to follow her?

Borrowing a tactic from the business world, the Star performed “360 performance reviews” of the leading contenders in the mayoral race. We talked to people all around the candidates — those who have worked above them, next to them and under them — to understand their strengths and weaknesses as voters prepare to decide who will be Toronto’s next leader.

Early in Ana Bailão’s first term as councillor, then-mayor Rob Ford, an unpredictable leader whose proposed service cuts shocked the city, brought a plan to council to sell off 675 Toronto Community Housing properties to private investors.

With 86,000 families on the waitlist for public housing, the unloading of these properties — a collection of single-family homes scattered across the city — was an unpopular pitch.

Bailão, a rookie councillor, had recently become chair of the city’s affordable housing committee. Then considered a low-profile portfolio, housing would become, over the course of her 12-year council career, one of Toronto’s most urgent challenges.

Bailão consulted with experts, then met with Ford and negotiated a compromise: they would sell 56 unoccupied homes now, while establishing a task force to explore options for the rest.

Ford, elected on a promise to stop the “gravy train” of wasteful spending at city hall, agreed.

That deal, which saved more than 600 community housing properties, was among the first brokered by Bailão in a move that would shape her reputation as a consensus builder who works effectively across ideological lines and a strong advocate for affordable housing.

A centrist with a progressive bent, Bailão has built a political career on collaboration and consensus. At city hall, where she was both a councillor and deputy mayor until 2022, people who worked with or for her say she was known for the kind of behind-the-scenes political grunt work that is often not visible to the public: shopping proposals around to councillors, getting ideas costed with staff and grinding out deals.

Some view consensus seeking as a weakness in politics. Critics have questioned whether, as mayor, Bailão could go to battle with provincial and federal leaders, or if her conciliatory approach would leave Toronto in a weak position.

The times we’re in require a mayor who cannot only govern effectively, but inspire, lead public opinion and make bold visionary moves. Even some who respect and support Bailão wonder whether she can be that person.

Supporters acknowledge that her collaborative leadership style may not get the attention that some grandstanding and bombastic members of councils past have received for loudly opposing certain proposals, but say her strategic approach gets the work done.

“She has never been a person who’s focused on grabbing the spotlight,” but “she has been a key player on many issues,” said former Toronto mayor Barbara Hall, who has endorsed Bailão.

Those who believe she’s the best candidate say voters need only look at her background to see evidence of the tenacity and life experience that make her well-suited for the job.

Bailão, 47, came to Toronto from Portugal as a teen in the early 90s with her six-year-old sister. They joined their father, a construction worker, and mother, a seamstress, in a multi-family flat near College and Lansdowne, where she learned first-hand how access to affordable housing is critical to building a life here as a newcomer.

She arrived speaking little English, but learned the language quickly and became her family’s leader, attending her sister’s parent-teacher interviews and accompanying her parents to meetings with bankers and lawyers. “I had to grow up very fast,” she said.

After school each day, Bailão delivered her little sister home to their father, then met her mother downtown where together they worked cleaning office buildings from 5:30 to 9:30 p.m. She still remembers her first paycheck: $237.

After graduating from the University of Toronto, Bailão worked as a morning news reader for CHIN Radio, as a political assistant for a Toronto city councillor and as a banking executive.

She lost her first run for Toronto city council in 2003, but tried again in 2010 and was elected to represent her ward, Davenport, in the city’s west end.

Today, she worries that as Toronto becomes increasingly unaffordable, newcomers no longer feel the sense of possibility she did when she arrived in Canada. “The identity of Toronto, and the soul of the city, is tied to that feeling of opportunity,” Bailão said, and that’s what drives her focus on affordable housing.

Complicating Bailão’s record on that issue is the Housing Now program, which launched in 2019 when she was deputy mayor. Meant to rapidly produce thousands of affordable housing units, the program has struggled amid numerous challenges and has yet to produce a single unit, leading some opponents to call it “Housing Never.”

As a politician, Bailão is known for her strong work ethic and due diligence. She needs to know her files deeply and insists on having all the details before making a decision, former staffers and colleagues said.

“She won’t get outworked by many people,” said former council colleague Josh Colle, who with Bailão and Mary Margaret McMahon, another former councillor, made up an informal voting bloc they called the Mighty Middle. (To others, they were the Mushy Middle.)

“She’s calm, but she’s not afraid of putting people in their place either,” McMahon said. “I’ve seen it firsthand.”

Facing challenging times, Toronto needs a leader with integrity, someone who “even if you disagree with her position, she still has a way of commanding that respect,” said Braden Root-McCaig, her former chief of staff, who is currently working on her election campaign.

That integrity has earned Bailão strong professional relationships with colleagues across the political spectrum, so much so that when she was charged in 2012 with impaired driving, councillors from left and right stood by her. Today, Bailão calls the DUI “the biggest mistake of my life.”

Bailão has earned the support of numerous sitting councillors, major labour unions, MPs and former mayors Barbara Hall and Art Eggleton, and she is well-liked in her Davenport riding, where she was re-elected in 2018.

But she is not well known to the public outside Davenport, perhaps in part because the passion seen in Bailão at community barbecues and events doesn’t always shine through at city hall, where her manners and restraint can read as corporate or stilted, some who worked closely with her have noted.

“I can be loud,” Bailão said over coffee on a park bench near her downtown campaign office one morning in late May. When former mayor Rob Ford first proposed selling the community housing properties, “I took buses of tenants out to Parliament Hill to protest,” she said.

“I can be very loud,” she said again, eyes flashing as though she was preparing, at that moment, to prove the claim. “But,” she said, returning to her default calm, “you need to be strategic at certain points in time as well.”

And that, she believes, is a strength: knowing when to fight, and when to be strategic.

I can be very loud. But you need to be strategic at certain points in time as well.

ANA BAILÃO CANDIDATE FOR MAYOR