I would not judge the Man.
1st he is a Lib so he most likely supports Cannabis legalization.
2nd I lived in Toronto for the time he was the chief and I never once got harassed for Pot. (The only people I hear of getting harassed are Gangsters and G20 protesters)
3rd None of the Cannabis clubs or Vapor lounges got harassed by the Toronto police during his tenure.
The only real stain on him IMO is G20, and that arguably was not even in his control. I think the PM and the RCMP and Army and all the secret services from around the world are who had control during that event.
I would also add that maybe because he was a Police chief he might have a better insight has to what needs to get done in the city and maybe his input has a politician will serve us good, specially if he is pro Cannabis, or at least Cannabis friendly.