Such a candidate could be elected in Toronto. One has already (twice) - David Miller.
And before anyone trots out any one of those misleading/insidious coloured ward maps showing which mayoral candidate won each ward (purporting to show an urban/suburban split in the vote), let me stop you. Those maps imply that the mayoral election is a first-past-the-post race where the winner is the one who has the highest tally of wards - somehow like the fight for ridings in provincial and federal elections. Not only did Miller win the most votes in some wards in Scarborough, North York and Etobicoke, but he placed strongly throughout the city (e.g. in Rob Ford's Ward 2, arguably the epitome of 416 inner suburb, Miller got 4631 votes to Tory's 5344 - with Hall and Nunziata at 1465 and 1332 respectively). Let's not paint all voters with the same brush - there are people in Ward 2 who care about urban issues and the public realm, and there are people in Ward 28 who think DMW makes a lot of sense.