Ana Bailao….See you in 2026

Olivia Chow was elected Toronto’s next mayor in an unexpectedly close race on Monday, promising to bring a more progressive approach to the city after more than a decade of John Tory at City Hall. The former downtown Toronto NDP MP and city councilor was up against 102 candidates that included a half dozen established contenders.

Among those rivals was second-place finisher Ana Bailao – a past deputy mayor to John Tory, whose resignation in February triggered the byelection. When doing my postmortem review, it appears that Chow was able to win all of Toronto’s downtown wards – including Bailao’s former ward of Davenport and five of six wards in Scarborough. She secured at least 37% of the total vote share.

Ana Bailao, managed to win in all three Etobicoke wards and all of the north Toronto wards except Willowdale, capturing about 32% of the total vote share. She captured just over 235,000 votes and elevated her to second place. You may suggest that a close second place is not winning, but in this case Ana Bailao had the momentum but was a bit late in taking it over the finish line. John Tory gave no interviews after the election and only sent out a presser and congratulated Olivia Chow. However, Tory still managed to loom over the election to replace him via an eleventh-hour endorsement of his former deputy mayor Ana Bailao.

Was it too little, too late?

The undecided vote was still around 15 to 20% about 24 hours before election night and many folks were asked to vote strategically as opposed for the candidate of their choice. In other words, a vote for say Saunders would be a wasted vote, especially if you were not a fan of Olivia Chow and the NDP or the progressive movement. Why Ana Bailao received a large shift of votes in the last twelve hours before voting ended was because the stop Chow movement worked, but it was too late. Saunders bet on a public safety platform that sought to balance more police with more community investment. But in an election that was primarily focused on housing and affordability Saunders was seen by many as a policy lightweight.

It seems as though John Tory made the right decision to support Bailao but it was too late. He also at first did not seem like he really wanted to be out there, however, the commercial by Mr. Tory seemed to pick up in context and believability. On a personal note, l believe that he was forced to make the move and in fact l thought the timing was just right from a political perspective. The reasoning is that if Tory would had come out earlier, there would have been more scrutiny on Bailao and Tory which could have backfired.

Josh Matlow and Mitzie Hunter came fifth and sixth respectively – possible victims of surge to save Chow. They may have lost but they are winners especially Matlow and Bradford who both return to city council and keep their jobs. Mitzie Hunter is the only one that resigned her position to run for mayor of Toronto. The person that impressed me the most other than Ms. Bailao and her pure maturing in front of everyone was Anthony Furey. Many think that he is some far-right wing nut that needs to be contained and brushed off. His surge within the last 5 weeks of this campaign gave him solid recognition and a sense that he could also be in the mix for a future political career.

The Ford movement this time was not a charm for Saunders who was given an endorsement by the premier along with some robo calls to Ford supporters.

Doug Ford went from staying out of the election race to warning Toronto not to vote for a left-leaning mayor, to actively campaigning for Saunders in the final days of the race. He still holds plenty of cards though, given how much power the province has over city affairs.

Ana Bailao was someone that l needed initially to be convinced that she was a candidate worth supporting for mayor of Toronto. As l got to know her and communicated with her on the issues and conversations about strategic planning for the campaign, l was pleasantly impressed.

She has experience at City Hall playing the political game, but this campaign has elevated her into a category that saw true political growth. This ten-week campaign in my humble opinion has elevated her into someone that will be recruited by other political movements either federally or provincially. But l feel that her calling is the mayoralty job, and she will be our next mayor in Toronto.

Its very easy to be critical of politicians and many of them are full of hot air, but the ones like Ms. Bailao who take a risk and was out there promoting her brand is not an easy thing to do.

Politics is all about timing and when one door closes, another will open and for Ana Bailao she has a tremendous upside in the political game if she chooses to continue.
Well played campaign!

Vince Nigro/MS