The fight on the right and the centre split: Why Olivia Chow's rivals are struggling to catch up

Standing on a stage on Monday, surrounded by supporters holding up her purple campaign signs, Olivia Chow played to the crowd.

"Are you ready to elect a mayor who cares?" she said as they cheered. "Let's go do it. Let's make it happen. Let's win."

It was the first of two rallies that the front runner's campaign plans to hold this week as Chow attempts to project confidence and seal the deal with voters ahead of Toronto's mayoral byelection.

And while nothing is certain ahead of election day, pundits and former councillors are already busy trying to understand how Chow jumped out to a lead after entering the race late, with her support only growing over the last month.

Some suggest that unlike her opponents on other sides of political spectrum, she is viewed as the lone standard-bearer of the left.

"She's had a clear runway on the progressive side of the vote," conservative strategist and principal at Earnscliffe Strategies, Shakir Chambers, said. "I think if we had just three candidates, one in the centre, one on the left, one on the right, it'd be a much more competitive race." 

Former city councillor John Campbell said the left coalition in Toronto is organized, has a solid volunteer machine and no matter who their candidate is, they will come out in big numbers.

And other campaigns haven't been able to land attacks on Chow that have stuck with voters, he said.

"To their credit, (Chow's team) put together a fairly solid campaign so far," he said. "The other campaigns haven't really been able to launch the missiles at her that have hit the mark."

Strategist and consultant Kim Wright credits Chow personally for the strength of her campaign. The former NDP MP is just being herself and that's winning over voters, she said.

"Authenticity has actually played the biggest part of this," she said. "And voters are looking for that. They're looking for swagger from candidates, looking for authenticity. And that's why you're seeing some of these fractured campaigns and candidacies."

Tough to stand out in crowded field

Campbell said no one should rule out unexpected shifts in the final days that could alter the race, but the vote is expected to be "splintered" on the right and in the centre of the political spectrum.

Campbell, who describes himself as a fiscally conservative liberal, said the competition for conservative-minded voters among former police chief Mark Saunders, former Toronto Sun columnist Anthony Furey and city councillor Brad Bradford limits their ability to gain traction.

"There's been no solid choice from the right from the fiscally responsible side of the ledger really to come forward," he said.

But former deputy mayor Denzil Minnan-Wong lauds Furey for his ability to communicate with right-leaning voters who aren't happy with the state of the city. He thinks that's why he's jumped in the polls in recent weeks.

"Anthony Furey's messaging has been spot on," he said. "He's been really clear in terms of taxes, in terms of safety. And because he's been so really good at communicating, he's caught on."

Margin of victory worth watching

But it's not just the right that's divided because of the vote split. The liberal candidates in the centre of the political spectrum — Ana Bailão, Mitzie Hunter and Josh Matlow — all sound similar despite a lot of policy coming from their campaigns, Campbell said.

Minnan-Wong said he'll be watching to see the margin of victory for the winner in this race. Depending on the percentage of the vote, the winner could face challenges on council, with people arguing they don't have the mandate to implement an agenda, he said.

"I would say that mandate affects what somebody can do," he said. 

Chambers said Chow will need her strength in the polls to materialize on voting day to not only win, but to ward off such attacks.