Here are some zones I think a supertall might not be amiss in - with some conditions. Missing from the map are Scarborough town centre and Sheppard and Yonge at the 401, which I think could both handle one or more. Also, the west end of the Bloor line isn't on here, or Sherway Gardens. Would a building there as a 'gateway' marker would be a good idea? (Like the singular Palace Pier used to be). Downtown Mississauga I could see eyeing a few - it's certainly got the room.
The areas that interest me are around certain subway stops and in-city industrial areas. Yorkdale shopping centre, I think, for example, could easily put a small cluster of highrises including some supertalls attached to itself without blinking. Planes leaving Downsview runway might have to fly as close to them as the Gardiner is to certain waterfront condos, but, hey - who's counting!?
Maybe a demolition and redevelopment of the area around Victoria park? Come to think of it, if those buildings were demolished, I don't think I'd want to see skyscrapers return there. I think they mar the sensitive landscape there. So - revise that. Not Victoria park.
Some in-city industrial zones, especially the ones around Eglinton / Don Mills particularly - are huge. If these were redeveloped as high-intensity mixed-use residential zones, they could be attractive. But that's a big 'if'. Within these areas, speculatively, a supertall might make a nice signature piece.
I'm divided on the Portlands. I champion Waterfront Toronto's current plans as they are to date - as they're actually real life plans!
But, while fantasizing and speculating, I like to envision uses there being a bit more vivid, one way or the other. (No, not anything like the Fords are bandying about).
I think the portlands would make a great waterfront central park for the city, in it's entirety. The whole thing. What a gift that would be! But, since I don't expect to see the entire site freely handed over to meadows, vales, orchards and bosky dells, the idea of it's densities being polarized into a waterfront park west of Cherry and a wholly new futuristic downtown core east of Cherry is tantalizing. This central block along between Lakeshore and the shipping Channel could be a good place for a cluster of competing supertalls. If the area was contextually developed around it to suit. With no new place to build huge office buildings in the old downtown - why not make a new one - still downtown?
I'm afraid to even mention this, given the current slavering over the place by current administration.
Then there's that wonderful series of lots and low buildings between Yonge and Cooper between the Gardiner and Queen's Quay. Not a bad place to consider, for one.
Anyway, something to think about. Toronto, seen from the air, is surprisingly far-flung, low-rise and suburban. And flat. There's no topography from which to view one part of the city from another.
I'd rather see us intensify within our current boundaries than continue to spread outwards. The notion of some new supertalls downtown continuing to demarcate the centre - but with outer ones as reminders and markers of areas we can't usually see from where we're standing, intrigues me. Supertalls as a unifying architectural gesture. It's a bit Hugh Ferris, but not an unpleasant thought.