I'm willing to dismiss one election as a fluke; a perfect storm created by a garbage strike, the HST, eHealth, a slate of bland right-leaning candidates with no credible predecessor on the left to fill Miller's shoes.
We have to remember that this is still the same city that elected suburbanite Mel Lastman with 80% of the vote, and urbanite David Miller with 60% of the vote, and that both mayors had extremely high approval ratings in both the core and the burbs for most of their two terms in office. I have little doubt that Tory (on the right) and Chow (on the left) could have similar crossover appeal. We also have to remember that this city has been incredibly unified in provincial and federal politics, that we care about far more issues than we disagree over (public transit, parks and rec, etc).
I'm still holding out hope that Rob Ford is an acute rather than chronic symptom. But only an election will prove that.