Skydome now Rogers Centre

Constructed late 1980’s – price - $500,000,000 plus
Sold 2004 – price - $25,000,000

Confederation Life now Rogers Campus, 1 Mount Pleasant Road

A friend said he knew that Confederation Life was going to go out of business as soon as the hoarding came down on their newly built HQ at Jarvis and Charles about fifteen years ago. This po-mo palace was evidence of a company drunk on its own profit margins. He was right – the company was struck a deathblow when the bottom dropped out of the real estate market in the early 1990’s and it had its clients' investments tied up almost exclusively in real estate.

source: http://www.erisk.com/Learning/CaseStudies/ref_case_clic.asp

Segregatory Zoning pre-1974 Central Area Plan

In the 1950’s and 60’s Toronto’s planners and politicians sought to separate the city into discreet use-based zones as was the vogue in post-war city planning. The fetish for segregation led to fertile conditions for developers to block-bust existing lowrise neighbourhoods and replace them with large slab-like apartment towers. Infamous examples include the crumbling Uno Prii designed 50 Stephanie Street, and St. James Town. For government, the folly of clean-slate development included the infamous “slum clearing” that lead to the creation of Regent Park, which now faces its own erasure fifty years later.

The Allen Road (would-be Spadina Expressway)

Part of a multi-pronged plan to thread the city with an extensive and interconnected highway network, today’s Allen stretches from Yorkdale Mall to Eglinton Avenue West. The balance of the highway was to run southwards from Eglinton to Harbord Street where it would join Spadina Avenue, and was known as the Spadina Expressway. Massive opposition to the expressway, in particular under the aegis of Jane Jacobs and Annex neighbourhood activists whose neighbourhood would have been stuck through like a kebab, brought construction to a halt in 1969, and led to cancellation of the highway by 1971.

Source: http://www.torontoexpwy.com