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Contemporary cities across North America are in crisis, and Toronto is no exception. Growing poverty and homelessness, mounting waste, air pollution that impacts residents’ health as well as the environment, inadequate transit, and failing infrastructure are issues that council faces perennially while trying to redress decrease in financial resources. The challenges are enormous. This paper will examine some of the issues facing Toronto today and consider directions for sustainable solutions. A considerable problem facing Toronto is that of growing homelessness. The city’s solutions have invariably been short-term band-aid solutions that fail to address the underlying problem. The removal of the residents of Toronto’s Tent City in 2002 was accompanied by the offer to provide housing in the old Princess Margaret Hospital (Dunphy, 2000). However, the housing was emergency sheltering only, and under conditions that far below acceptable standards—inadequate toilet facilities, poor air flow, high infection rate for disease, and rampant violence (Crowe, 2000). In addition, the shelter spaces opened at the old Princess Margaret Hospital increased the total number for the city by only 320. There are between 40 and 50 thousand ho