He won because lots of folks who live in Scarborough, Etobicoke and North York have 1.5-2hr long commutes to work. They aren't stupid. They know the LRTs won't do all that much for them (particularly if you're not on an LRT route ie, say on Finch or Lawrence and not on Sheppard).
The people want speed. They associate subways with speed. And that's why they pick any politician who offers them subways every time. Calling them "stupid" or saying that they are looking to reaffirm "entrenched beliefs" is simply not going to work. They care more about their long commutes than your name calling.