What's done often in Toronto is a tall tower anchored by a wider, residential pedestal. The "pedestal" is usually marketed as "lofts" as they have higher ceilings than the actual condo units themslves. So a pedestal/tower combo would work well to fill in the entire back lot.
This pedestal would also give tons of room for a rec centre to connect the Connaught w/ the Condo Tower.
Something like THIS would fit in nicely
http://www.condoleaf.com/users/up/Element.jpg