If you look at the polling and trends over the past few years, if math doesn't work out in Ford's favor.
Because of his contempt for them, Ford has almost no support in Old Toronto. That's more than a third of the vote that he won't be getting back.
For Ford to win he'd need incredible support in Scarborough, Etobickoe and North York. That incredible support doesn't exist. His disapproval raring has consistently been at about 50% in those three boroughs. And the fact that they'll be more than one subway champion conservative in the race doesn't help him at all. They'll surely grab some votes from the 50% of people there that still approve of his job.
Ford will be very lucky to get 40% in the election.