That there is the issue that got Ford elected. "I'd support someone like that to not support these idiots". He fooled everyone in the burbs long enough, and also his opposition fought each other, that allowed him to get in as the 'voice of the people'.
Would you have a chance? Well, if you don't try, you won't know. In theory, anyone can run. In practice? gotta know how to play the political game to get elected, use your words wisely, and always assume you're on the record.
John Tory would have been a great mayor (considering the competition) but he wasn't 'cut-throat' enough during debates and responding to other statements. Voters saw that as a weakness and went with someone they felt could hold their own (at least from the perspective of the image they were portraying).
Also, for someone getting in to politics, you gotta bring some (life) experience to the table. Justin Trudeau doesn't have a chance because he's quick at the lip and the counter to his campaign will simply be someone that has no experience or business sense to run a 2 car parade let alone the country.
The people that should be running, usually don't; when they do, they get swallowed up by the political/media circus. The cycle continues.