Ana Bailão

In 2003, Bailão worked as an assistant to Ward 18 Councillor Mario Silva and put her name forward as a candidate to replace him in the election that year, running on a platform focusing on environmental issues, tenants rights and reduced property taxes for seniors.[3] She finished in second place to Adam Giambrone.[4]

In the 2010 municipal election, Giambrone entered the race to succeed David Miller as mayor and did not run as a councillor.[5] Bailão sought the open seat in Ward 18. She described herself as "centre-left, maybe centr[ist]", running on a campaign of efficient service delivery and community involvement in decision making, and won the ward.[6][7]

Bailão in 2015

In 2012, Bailão led a working group to look into problems with the city's community housing stock. Earlier in the year, Mayor Rob Ford had proposed to sell off 706 city owned houses to pay for repairs. Bailão's group issued a report that recommended selling only 55 houses. She said, "We recognize that some of our proposals might not be popular. Some might want the status quo, while others will think we should have gone further. But we think we have found the right balance."[8]

In 2017, Mayor John Tory appointed Bailão as a non-statutory deputy mayor, for Toronto and East York – the city's south district – with a policy focus on housing.[9][10][11]

In 2020, Bailão voted against defunding the Toronto Police Service during the COVID-19 pandemic, despite the protest of local community organizations such as Black Lives Matter and Not Another Black Life.[12][13]

On her appointment as the chair of the Affordable Housing Committee, Bailão commenced to seek to move the housing affordability issue to the centre of public policy actions at the City of Toronto.

As part of this focus on affordable housing, in March 2011, Bailão convened a Symposium on Poverty, Housing and Homelessness that included the United Way Toronto, the Toronto Board of Trade, the Daily Bread Foodbank, and former mayor and Senator Art Eggleton.[14] The symposium was among the first major undertakings to examine the then emerging inequity evolving between various income strata and the impact of this dynamic upon the city's neighbourhoods and housing sector.[15]

2011 saw the City of Toronto contending with significant financial pressures,[16] coinciding with a reduction of funding from both the provincial and federal governments with respect to housing.[17] In recognition of this reality, Bailão and the Affordable Housing Committee established a roundtable which included private-sector experts to consider how the facilitation of more affordable housing in Toronto in the absence of funding from the other levels of government, eventually producing a report.[18] The plan included the creation of nearly 8,000 affordable homes and in excess of 13,000 well-paying construction jobs within 3 years.[18] This report was well received as it was perceived as a method under which affordable housing could be advanced in the absence of substantial public funding.[19]

In 2011, the Toronto Community Housing Corporation (TCHC) faced a repair backlog of $650 million.[20] In response, the Toronto Community Housing Board recommended the sale of 872 stand alone houses to offset these costs, with 715 TCHC houses considered recommended as viable for selling.[21] Excluding the 11 homes that had already been approved for sale by city council in previous reports, the TCHC Board recommended an additional 675 units be sold.[21] The public and media response to this proposal was highly negative,[22][23] with many groups voicing strong concern about how a large scale sell-off of affordable housing would affect the already over-burdened social housing waiting list.[24] Three former mayors of Toronto also wrote a joint letter to express concerns about this proposal to sell the scattered houses in TCHC's portfolio and imploring that Toronto re-engage the federal and provincial governments in sustainable funding support for the growing repair backlog.[25]

Bailão raised strong concerns about the impact of this sale to the City Social Housing portfolio. Bailão submitted a letter as chair of the Affordable Housing Committee to the Executive Committee, which was handling the TCHC report identifying these concerns.[26]

In response to these concerns, Bailão requested the opportunity to lead a special housing working group[27] in order to identify innovative solutions and creative partnerships. In its meetings on March 5, 6, and 7, city council approved Bailão's request and she was appointed to lead this working group along with management consultant Jim Pimblett, TCHC Board Chair Bud Perves and former cabinet minister Alan Redway.[28] This working group was created to make findings on the proposed sale of the 619 TCHC homes, develop innovative solutions and new partnerships to address the repair backlog and create a strategy to re-engage the federal and provincial governments in providing affordable housing. This working group was asked to report back to Executive Committee in early fall, 2012, in order to provide recommendations to city council.[29] Their final report, entitled "Putting People First", was released on September 17, 2012,[30] and was widely well received by social housing advocates.[31][32][33] By the time the final report was returned to Executive Committee on October 9, 2012,[34] the working group's report recommendations had been informed by consultations with over 600 individuals and organizations. As a goal, the working group set out to raise $120 million over the next two years for housing repairs.[35]

By 2013, TCHC's repair backlog had increased to $751 million.[36] In March 2013, another of the Special Working Group's recommendations was implemented and realized when $93.5 million was unlocked as part of the refinancing of 18 mortgages at lower rates through Infrastructure Ontario.[37] As a result, nearly $100 million was directed towards high-priority structural repairs in TCHC buildings.[38]

The approval by city council of the mortgage renegotiation also marked a significant achievement for the Special Housing Working Group's report. In addition to the already implemented recommendations from the Special Working Group, the original target of raising $120 million towards the repair backlog was achieved in only the first 6 months of the report receiving council approval.[39]

Bailão championed a Close the Housing Gap campaign which aimed to encourage the federal and provincial governments to continue funding social and co-op housing at existing levels as well as provide new long-term funding for social housing state of good repair work.[40] The end result of this work and advocacy was a 10-year state of good repair plan that included a $1.3 billion investment over the decade from the federal government in addition to funding from the City. This 10-year plan is the first of its kind in the history of the country’s largest social housing provider.[41]

Under Bailão, the Planning and Housing Committee developed a 10-year action plan to address Toronto’s housing challenges, the HousingTO 2020-2030 Housing Action Plan.[42] The work of the committee also resulted in the Enhancing Housing Opportunities in Neighbourhoods plan,[43] which included the approval of laneway suites, garden suites and coach houses which aimed at gentle densification in existing neighbourhoods.[44][45] It identifies the need to advance efforts to amend Toronto zoning regulations to allow for densification within the city's “missing middle” – areas of the city where only single-family dwellings are permitted.[46]

Bailão also led the City’s Modular Housing Initiative, which aims to quickly deliver supportive housing to those experiencing homelessness or who had a history of chronic homelessness.[47] She also worked on development of Toronto's Housing Now program, which was launched in 2019 and seeks to repurpose city-owned land for the development of affordable housing.[48] Bailão supported the creation and implementation of the Open Door Affordable Housing Program in 2016, which aims to "streamline the process for developers who want to work with the city to build more affordable housing".[49] Another program supported by Bailão is the Multi-Unit Residential Acquisition program, which provides $20 million in grant funding and City Open Door Program incentives to non-profit and Indigenous housing providers.[50]

Bailão advocated for the implementation of a vacant homes tax, which seeks to increase the housing supply by encouraging property owners to list their vacant houses, making them available to the rental housing market.[51]

Bailão announced in May 2022 that she would not be seeking re-election to Toronto City Council.[52]

In September 2022, the Building Industry and Land Development Association honoured Bailão's work in addressing housing supply and affordability.[53]

Following the resignation of Mayor John Tory, Bailão was widely speculated to be a potential candidate in the then-upcoming mayoral by-election. She explored launching a campaign with political strategists Tom Allison and Nick Kouvalis, who both advised Tory's campaigns.[54]

On March 17, 2023, Bailão announced her intention to run for mayor of Toronto.[55]

Bailão has proposed reversing Toronto Transit Commission (TTC) budget cuts by uploading the city's municipal expressways – the Don Valley Parkway and Gardiner Expressway – to the provincial government, which would annually save $200 million.[55] She highlighted the need to boost ridership back to pre-pandemic levels.[56] Bailão also discussed expanding cellular service in the TTC subway system, describing it as a "convenience and safety issue", and stated that telecom providers have a "duty" to work with the city, which major firms have refused to do.[54]

She has indicated she does not support the new strong-mayor powers brought in by the province which allow by-laws that align with provincial priorities to be passed with one-third support on council and disagrees with Tory, who requested them.[56] However, she indicated that she supports the new powers which enhances the mayor's influence over the city budget, including the power to veto amendments.[56]