I hate to be Devils Advocate and i'll also mention im Toronto born and raised and i love it here. But the feeling i get from most Americans is, they think of Canada as small time in comparison to the USA, even tho Toronto is bigger then most American cities and is much more diverse and multi cultural, i really think most American players rather play in the United States.
That being said, theres a few cities like Orlando, that dont have strong fan bases and are mostly tourist/college towns, that have the same problem, and i think Orlando might have a problem keeping Dwight in the future. We need a culture of winning here in Toronto and we really need to make our players feel welcome, because its easy for them to just say, screw this, ill sign somewhere else down the line. Most Toronto fans i meet (i have yet to really get to know this forum) will turn on players and their team at the drop of a hat, which i think hurts our situation aswell, we are a negative, half empty kind of sports town most of the time