Wait a minute, this is all wrong. The original point of contention was that Toronto's architectural history was, on a "building by building" basis, "far better" than New York's or Chicago's. Without getting into whether or not the box is the end of architectural history, this is untrue. It is silly to judge historical anything by modern standards. No new building should be built with a Zeppelin dock, but a building built when Zeppelins were a legitimate form of travel shouldn't be disqualified because of it. An "anachronism" is something which is chronologically misplaced, Art Deco buildings fit in perfectly with their time in history and so have most architectural styles. I might as well deride the Parthenon because they didn't have the wisdom to build it with curtain glass walls. And how is 19th century Chicago an example of imperialism? The US barely even had a standing army at that point. Simple concrete blocks where the favored architecture of the Warsaw Pact, the 20th Century's largest empire, yet I see no denouncement of the TD Center as "imperial."
I'm also skeptical to the degree that modernism is really all that functional. Compared to what? Maybe compared to turn of the century neo-classical skyscraper with arches and such. Other than that though, the most "functional" buildings are probably the suburban office parks and super-centers that have characterized most construction since the '50s. When the Google wants to build a new server farm, they move to Utah and slap up a warehouse. The only people who can really afford to locate in shiny modernist skyscrappers are hedge funds. Given the rise of various IT solutions (i.e. teleconferencing), you could plausibly argue that skyscrapers themselves are anacrhonisms, which is partially why the only people who can afford to build them (big banks, multi-national companies, governments) treat them like status symbols.
I don't think that means we should stop building skyscrapers, or even that we should move away from modernism, just that this constant harangue about everything needing to be a perfect rectangle for fear of insulting the gods of modernism over, gasp, putting some emphasis on form over function is inane. The very idea of skyscrapers tends to put an emphasis on aesthetics and symbolism over practicality. A movement whose head figure wouldn't let people control their own blinds for fear of ruining a facade shouldn't lecture on how function should come before aesthetics. If you didn't care about how a building looked, you would move to Idaho. It's like the fashion designers who claim their, inevitably impractical, designs are more practical for real life, oblivious to the idea that if people really cared so much about function they would just were Crocs and jogging pants.