I pretty much concur with potatolicious' assessment. I'd just like to add that it took some visionary thinking to get to where we are today. The city anticipated during WWII, that cars would be the preferred mode of transportation for many more people when the war ended. Instead of building just freeways, the city transit commission went to work planning public transit around rail. At first streetcars were to be used and would just run underground, but eventually the idea morphed into a fully fledged subway system.

That's not the only example of forward-thinking. There is a huge urban valley in Toronto called the Don Valley. In 1918, Toronto decided to build a bridge connecting roads on both sides of the valley and the designer figured "hey, why not build a lower deck capable of holding two lanes of rail traffic....just in case?" About half a century later, when the subway was being extended, they just ran the line through this bridge. In today's fiscal and political climate, a similar decision would never be made. In fact, I'm positive that 50 years from now, future Torontonians will look back at us with frustration at our shortsightedness. Funny thing about that bridge... it can hold 5 lanes of car traffic with sidewalks for pedestrians to boot. The designer successfully designed a bridge to last more than 100 years. It's an incredible accomplishment.

I just want to elaborate on my first post. Toronto's transit system's problems aren't all due to the union of course. They bare the brunt of criticism these days, but the truth of the matter is financial and political backing of the system at provincial and federal levels pretty much stopped happening at the beginning of the 1990s. The federal Liberal government was voted into power in the early 1990s at a time when Canada was dealing with its own financial crisis, not too dissimilar to what the U.S. is facing now. We had all these social programs financed on deficit spending. The Liberals slashed spending on a lot of programs, and Toronto's transit system was one of them. A few years after the Liberals got into power, the Progressive Conservatives were voted in at a provincial level and they also slashed spending. They "downloaded" some social programs onto cities which affected municipal budgets drastically. So basically, the Toronto Transit Commission (TTC) has been cash strapped for the better part of 20 years now.

Things are so petty here that when our Prime Minister announced stimulus funding last year, he flat out rejected Toronto's request of money to build out the TTC infrastructure because it "didn't meet the criteria" (details here: http://www.blogto.com/city/2009/07/a_look_back_at_torontos_s...). Days after the rejection, our PM decided to fund a $790M mass transit system for a small university town an hour away from Toronto (one which he hopes to win votes in and probably will).

In any event, transit riders in Toronto are the ones getting screwed. It costs $3 for a one-way cash fare. The system is overcrowded. The infrastructure is getting old, although the TTC does a good job of keeping old workhorses running. You know those old GM "fishbowl" buses originally designed in 1959? We still have some of these clunkers operating on routes today (http://en.wikipedia.org/wiki/File:TTC_T6H_5307N_Bus_2284.jpg).

On my more cynical days, I'm of the opinion that Toronto eventually needs to threaten to secede from Ontario (http://en.wikipedia.org/wiki/Province_of_Toronto) in order to ensure we get our proper share of the tax money so that we can spend it on things that matter to us like mass transit. The provincial and federal governments love to take our money and then not give much of it back when we truly need it.