I have been looking online but I think my memory is from work so I can't find public examples but development applications include a list of street names, a reason for those names and they are generally all around a theme. It's not exactly the same thing, but cbc looked at Vancouver street names and you can see themes within neighborhoods https://newsinteractives.cbc.ca/longform/streets/ If someone dug up the original planning application it might say why those names were selected.

My guess is that it was probably considered generic enough back then, and a reference to the buildings that bear his name near Central Park. There is a hotel and two condos very close to the park with this name, all being renovated/renamed in the late 80s through 90s. The land for the subdivision in Ottawa was bought in 1996. Maybe the developer looked up to him?

This was before the Apprentice, for example. So while people might have known he was a bad dude if they followed the business world or civil rights it wasn't necessarily common knowledge. It's probably important that I specify "in Canada" or "in Ottawa". Coverage of his shenanigans would have been less outside of the states. Maybe the city employee who okay'd the name just wasn't aware?

The subdivision also has a street called Bloomingdales after the department store. Whitestone and Grammercy are (presumably) named for affluent neighborhoods. So I guess they were going to this idea of wealth and glamour?

Anyways, there are more rules about naming streets after people now. I think we've all learned that sometimes this doesn't age very well 😅