I somehow doubt Rob Ford will ever be known as the tiny perfect anything.
Besides...I don't think anybody thinks of Crombie in that way really.
This is the Internet, remember. And among a certain skyscraper/project-loving contingent, there *are* those who'd like to frame Crombie as some kind of anti-world-class evil killjoy. Of course, they're not unlike those who still, to this day, raise the matter of Layton/Chow living in subsidized housing--or Obama birthers, etc.
The reform council wasn't really against head offices in the financial district....they were interested in social justice and saving neighbourhoods from downtown expressways and turning everything into St Jamestown. We got FCP at the time, but we also got things like St Lawrence neighbourhood too. You know....back when the world came to study Toronto because it had become somewhat of a model for urban planning.
Though to some extent, FCP (much like the WTC) was a grandfathered-in dinosaur condition, urbanistically speaking--nonetheless, there were other, external reasons (70s economic slump, oil crisis, etc) why the number of office towers built diminished (and *everywhere*, not just Toronto) after the early 70s, despite what some hardcore "Crombie the killjoy" types'll tell you.
But to return to the "mass appeal of heritage" issue: regardless of whether it was correct of City Hall's builders to do so or not (and I can accept how it might have been deemed "correct" at the time), the fact that the same general public that adores Viljo Revell's creation can snap into "oh dear, Toronto doesn't respect its heritage" mode when confronted w/pictures of the Registry--and with said reflexes at an odd disconnect from one another--is telling you something.
Though whether that means that the general notion of "heritage" has become easy-to-like "mass appeal" to a fault is something to consider--almost like *it's* the, uh, lovably rumpled, warts-and-all Ford to the slick Smitherman-esque longing for big starchitect schemes like Mirvish/Gehry. (And much as in the 2010 election, maybe the fundamental problem w/the latter camp is its odd condescending myopia t/w the former camp...)