[esquire]

The 60s and 70s were pretty savage when it came it to demolition of old buildings, but by the 80s it toned down significantly. Since then, I'd say that demolitions of prominent heritage buildings have been fairly rare... Eaton's is the only really big one I can think of in the last 20 years or so, although I'm sure there have been a couple others.

I'd say Winnipeg has done a really good job since the 80s of fixing up its stock of older downtown buildings. Part of the reason why Winnipeg didn't see a building boom in recent years is because so much new office space and residential went into older buildings that were either largely vacant or heavily underutilized before. It's a feather in the city's cap.