The art to install street lighting poles or what is this? Why so many?
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In the top image, the middle pole appears to be the TTC's to support wiring for the Streetcar; the other two are streetlights. Though I don't know why they would need one on that side of Wellington........hmmmm
Hydro and the TTC used to share poles, and still do on a legacy basis in some spots; but the TTC is adamant about not sharing w/them; something went awry between those two organizations and they decided not to share anymore. Thus doubling the number of poles required along TTC Streetcar routes.
If its not a TTC pole, the alternative is that the City wants to mount a traffic light on it; because the City doesn't want its intersection poles shared with streetlights, where possible, either.
Government cooperation at work.
The two street lighting fixtures exist in that image, because one is meant to provide light primarily to Wellington, while the other is to provide light to Church Street.
Is light necessary in both spots? Yes, there would be a gap of light coverage that would create shadows which might make an accident more likely..
However, the light need not be at that exact spot, height or style.
A very good case could be made here for a '"Victorian-Style" Bollard light, with the lighting coming out at about waste height, it can be set-up to push light both up and down to ensure proper coveage, and would significantly reduce the visual infringement on the Flat Iron.
But there are other additional options, because lighting can be quite powerful, and directional, it would be easy enough to Mount lights on the roofline or terrace line of one of the nearby buildings to illuminate that spot.
Lots of choices, but you have to care first, then think, then design, then do, in that order.........on this project every step was missed, more than once.