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Originally Posted by Steely Dan
One big takeaway from spending two decades on SSP as an American:
Do not give any credence to Torontonians and Montrealers when it comes their opinions about their respective rival cities.
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The rivalry between the two has softened in the past two decades; I think both cities have found their respective groove and don't really compete with each other for the same audience, so to speak. Peak rivalry was probably in the 50s when Montreal was a much more English-speaking city and there was a high chance that both cities would face off against each other in the Stanley Cup finals (no chance of that now!).
Montrealers and Torontonians are also probably going to be the people with the most experience with the other city, at least among cities that are on the same plane (so not places like Hamilton or Quebec City or even Ottawa), so they'd be able to give a somewhat informed viewpoint, and not that of a one-time tourist. It's kind of like how I'd weight an opinion about Dallas more from a Houstonian than from a Vancouverite.
In the grander scheme of things, Toronto and Montreal aren't that different from one another. The cities have a different personality and look different at street level, but a lot of "life" is kind of the same in both cities. Montreal has more in common with Toronto than it does with a city that it might look like on a superficial level like Philadelphia.