I don't use "plan" in quotations out of mockery, I use the quotations because the above has no official status with the city. While there was consultation done, the plan never went further than the visioning stage; it failed to receive funding to get the shovels on the ground. Such is the nature of city politics sometimes. Denise hung onto the "plan" however, and did her best to implement it piecemeal as the area developed.
Carlaw/Dundas is a relic of the working class neighbourhood that existed in the area back when several manufacturers had factories here. To this day, there is a very industrial "look" to many of the buildings in this area, as they've either been turned into artist studios, or have been "re-purposed" to keep the flavour, but with a new use. Consider some of the new condos that have appeared on Boston Avenue to the east, just above Queen Street; they "use" the facade on the Carlaw side to help keep the look and feel of Carlaw intact, while using the redevelopment as an opportunity to put in a new tree-lined sidewalk as per the "plan."
Of course, not everything in the "plan" is working out smoothly; issues with landowners has stunted development near the "rail spur", and while the zoning by-law tried to keep a "live/work" character to the neighbourhood, some of the new development has gotten OMB approval to increase their densities at the expense of the "work". The amount of new construction has frustrated residents as well; when I worked there, there were three new buildings under construction, and another three proposed. This was after the construction of the residences on Boston Ave, and a group of new residences on Colgate Ave. This is an area under change, and without the official graces of city council, a piecemeal solution can't solve all the problems.
I can't say I know Jack well; I met him once back when I went to school at Dalhousie, but I've never been a strong NDP supporter. I can't truthfully spin some tale about how "Jack knew how to bring people together" or whatever have you. I couldn't even tell you what he was like as a city councillor (beyond what Wikipedia says).
I can say that "Neighbourhood Improvement Plans" -- such as the above -- are a great exercise to envision how a neighbourhood can change. The "plan" is no "socialist" fantasy; it borrows from the philosophy of Jane Jacobs, reusing old buildings for new, while improving the pedestrian environment, creating green space, and allowing for new development when appropriate. I don't know what Jack personally left for the people in the riding he once held, but I know he tried to give the people who lived near the Carlaw/Dundas intersection a vision for how their neighbourhood could change.
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