I don’t see how we can’t win to be honest, his strategy whether it's by mistake or by design is genus. It’s me versus the establishment (i.e. liberals, intelligencia, the media), I’m an everyday Joe like you, speaks volumes to his base. He has a loud voice regarding his record, and can strong arm any debate right now and drive these messages home regardless of current opponents who may appear. Another conservative candidate needs to appear, and thus perhaps split the vote, we know there will be a few on the left who will run.
Except this has been a political trend that may be on it's way out - I see Ford as an increasingly outdated relic of 80s and 90s politics.
The "guy you want to have a beer with" is starting to lose its appeal...