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Now this one seems to have the old Globe building intact--I'm assuming the spires in the foreground are part of that. I *think* the framing for the BMO building went up in 1938 or 1939, so this narrows it to between 1931 and then.

And the new Globe and Mail building was completed in 1937. I'm not sure how long the old one sat before being torn down, but it seems to be pointing at a mid-30s date for the Imperial.
 
Another interesting shot of the Imperial Bank from the Star archives 1968, just prior to its demolition. Something was lost in terms of setting off Mies' pavilion when these masonry-clad, built-to-the-lot-line buildings were replaced by Commerce Court's rather awkward plaza on King Street:

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Caption: 1968 caption: Strangled in winter's grip, Toronto downtown intersection of King and Bay stands empty except for gently falling snow yesterday while city snowplows fought to cope with the blizzard's effects and get traffic moving again. On Friday and Saturday, a total of 7 inches of snow was dumped on Metro streets, and cost to the city of digging out and carting snow away was estimated at more than $1,000.000. Last Published: 12/30/1968


1948 view down Bay. Note the old Woolworth store is being excavated at Adelaide and the Bank of Nova Scotia is under construction at King.

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Now this one seems to have the old Globe building intact--I'm assuming the spires in the foreground are part of that. I *think* the framing for the BMO building went up in 1938 or 1939, so this narrows it to between 1931 and then.

It's only one spire. The other one's a shadow.
 
From The Toronto Daily Star Sat. Dec.27, 1969 (Special Edition on "The Challenges of the 1970's"):

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From The Telegram, Thurs. Feb. 28, 1963, special supplement upon the opening of the University subway line:

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That's very interesting concerning the proposed evelopment atop the bus terminal at Eglinton station! I really hope they're able to lock down redevelopment of that land soon - it's been languishing for too long.
 
Two more shots of the Imperial Bank from 1947 (FAC33, look what you started). Looks like the Cawthra House has just been demolished and the rest of the site is being cleared for the BNS Building:

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