Does Ana Bailão have a path to victory?

If you haven’t heard, it looks like we will be having a municipal by- election sometime this June or July to elect a new mayor for the City of Toronto. The minute John Tory submitted his resignation and vacated the seat on Friday February 10, 2023 at 5.00 pm the floodgates opened and the “games are on election” about who will replace John Tory as the next mayor of Toronto.

Just to put some context on the by-election, anyone who gets 25 signatures and pays a $200 registration fee can be in the race and put their name on the ballot. The unfair part of this election is that if a sitting councilor decides to run, he or she will not have to give up their seat. This is double dipping and should not be allowed and if you are a sitting councilor and decide to take a stab at this spot, a by-election should happen for that seat.
The minute John Tory made his announcement to step down my cell phone started ringing off the hook with the question about who will be the next mayor and who should we rally to support in this contest? Many political strategists and political operatives were jockeying into position requesting support and contributions for one of the possible horses in the race. On Friday February 11 many possible names were kicked around, and some great names were mentioned along with many other names that have no real reason to even be mentioned. I will share with you many of the names that have been bandied about and give you my prognosis of who l feel has any chance of winning.

Gil Penalosa….

He finished in second place in the 2022 municipal election and has announced his intention to run for mayor of Toronto. Penalosa, who earned roughly 18 percent of the vote was first out of the gate with chatter that he was in the race and was ready to replace Tory along with Chloe Brown, who also ran in the last municipal election and came in third place are just a small sampling of the candidates that had previously run in 2022 and have indicated early interest to run. In my opinion, these folks all have very little or no chance of winning this election.
Michael Ford is an early name that was put forward as a trial balloon and some early polling and surveys have been done to take the temperature of whether he has a chance of winning. The Ford machine needs a horse in the race because they have too much to lose if the wrong person wins this contest. Ford’s fingerprints are all over this election and as l have stated previously that the powers at Queens Park need to get their person in that seat for many reasons. With the new mayoral powers granted to Toronto and Ottawa it is imperative that Ford installs a very friendly presence in that spot. Michael Ford was the early trial balloon, but he has not been trending in favor of a possible victory.

News this weekend suggests Ford team will be less likely to support Michael Ford and put their support behind Mark Saunders, the former city of Toronto police chief. Saunders who unsuccessfully sought a provincial seat last year under the Ford banner is now at the top of the list of many of the Ford backers, not all of them… but the small ruling majority that makes up his backroom support. A smaller group of Ford supporters are split between Ana Bailão and Brad Bradford. The people to really watch where they go in my estimation is Ford’s campaign boss and the real brains behind Ford’s victories and that is Kory Teneycke who is backing Brad Bradford a young councilor from the east end.

Ana Bailão a Liberal who was Tory’s point-person on affordable housing, has been assembling her team to take a run at this spot. Her campaign includes Liberal hack Tom Allison, once an advisor to Kathleen Wynne and Nick Kouvalis, a pollster and fixer for many politicians over the past ten years. Mr. Kouvalis was one of the key people in the Rob Ford campaign that got him elected as mayor of Toronto. She will be in the race and could come up the middle depending on how much the results get split. The unfortunate problem for Ms. Bailão is that with many other candidates on the center/ right of the political spectrum, it will enable a candidate from the left to win this campaign. Ms. Bailão’s campaign needs to mitigate and convince other folks to stay out of the race and not water down the vote that will be very weak, and, in my estimation, a low voter turnout. A winning campaign in my estimation will need between 120,000 to 150,000 votes to secure a victory.

With Joe Cressy and Michael Layton, the original NDP great hopes both bowing out for reasons that still boggles my mind. The only hope on the center/ left is Josh Matlow who is a formidable opponent. A progressive councilor from north Toronto who has been one of Tory’s most vocal opponents at City Hall. From where l stand, the NDP have an unbelievable opportunity to pick up this spot if they all rally behind either Matlow or their chosen candidate. Traditionally, with lower voter turnouts, the NDP always gets their core supporters out and this situation favors the NDP candidate if they put together a strong run. Because the left is still struggling with who will lead them, Ms. Bailão as a moderate should be working with her team to sway them to support her which will be the only way that she would have a path to victory.

The two dark horses to watch are Brad Bradford and Dennis Mills. Mr. Bradford is touted as the new young fresh face with conservative political leanings that may just get all the Ford support if the other candidates get no traction. Again, l keep going back to Ford and who he is supporting because it would be disastrous for his supporters, especially in the development community if the wrong person gets elected. On the other hand of the age spectrum you have Dennis Mills who is 75 years old and wants to run for one term. Mr. Mills, a former Liberal MP from the Danforth area who has an unbelievable rolodex of solid contacts across the political spectrum, is someone that should not be taken lightly if he jumps into the race. Dennis Mills whose family have run Chairman Mills for years in this city and have very deep roots in the culture and fabric of this city will be a formidable candidate who really knows Toronto and what it needs thus a stable experienced hand at the helm of the city.
I would be remiss if l do not mention an old colleague of mine who will be throwing his hat into the ring and that is Giorgio Mammoliti. Giorgio, l love you, but you would only be taking some support away from folks that could truly win and maybe it’s time to move on.

This campaign will come down to the candidates on the center/right not splitting the vote and preventing the left from coming up the middle to victory. This city is at a crucial crossroads and truly needs a steady hand at the helm.

Vince Nigro/MS