Isaidso, Calgary has an entire 5-block stretch of buildings built over a century ago right in the core, with several mid-rise and high rise buildings from 1915 and earlier nearby as well, and several nearby streets with entire blocks of century old buildings. Just because Calgary is perceived as new and shiny doesn't necessarily mean it is, it only means we didn't stagnate for decades. Calgary may not have the historic influence of Hamilton, but we're really just missing a high-rise historic office tower like the Pigott Building and it would appear at par. Afterall, while Hamilton was about 120 000 in the 30s, Calgary wasn't too far behind with 80 000.
Also, Windsor has quite an impressive stock of historic high rise offices, 3 towers I believe? Not bad for a city its size. I wish one of the rail companies had built a grand hotel there to complete the stock! Unfortunately for Windsor though, so much of their core was bulldozed for cheap 60s crap.
Also to note, history/historic buildings aren't what make a city. They can add interest and layers of different architecture when viewing the city, and inspire thoughts of a grander time, but it's not an imperative. Just look at Shanghai, Seattle, Tokyo or Hong Kong...
I think we idolize history so much because what we usually perceive as the most interesting and cultural cities on the continent have so much historical architecture, New York, Chicago, Mexico City, Boston, Toronto, Washington, etc. But this is changing as younger cities develop their culture and build newer and interesting cultural centres like Vancouver's Convention Centre and Calgary's UC National Music Centre... culture, vibrancy, and attractions are really what is important.
The underlying point of this comment is, Calgary and Windsor most certainly should not be lumped with Mississauga, Oshawa, or Brampton. I feel as if it may have been a directed attempt at offense, but no worries, people who haven't been here usually know nothing about it even after having been shown thousands of pictures on sites like this