I was recently on Newbury Street in Boston. Turning away from the nifty pay-for-parking machine (these things have replaced meters on the street, and they couldn’t be more convenient, or more helpful for reducing street furniture clutter), I spotted this valiant little Gleditsia, working hard to stay alive:

A little way down the street was another Gleditsia, this one growing in a similarly sized tree pit, but intact from the saw:

Both trees work hard under severe limitations. The far tree shows what the nearer tree could have looked like.
How well these characters are doing is a direct consequence of how well they’re being cared for, and of their native vitality. The far tree is impressive for its growth despite the tiny volume of root space available for it; the near tree admirable for its persistence.
Go, little tree!
If a given location proves unable to sustain a tree (or at least one which meets the goals we had in planting it), it would be great to have in place a mechanism for deciding whether 1.) to invest the resources necessary to create a good growing environment, or 2.) to pave over that pit and put the resources somewhere (not too far away) where the chances of growing a healthy tree are greater.
In Boston, where sidewalks are narrow and stresses are many, that could mean a shift of trees away from narrow streets to broad ones. Or a shift of trees from both sides of a narrow street to one side only. Or on a narrow sidewalks (it’s less critical on broad ones) establishing a high standard for the construction of tree pits and the soils and plants that go in them — and not just on Newbury Street. In other words, we need to up our game or go home.
Or, alternatively, it might also make sense to consider the habit and growth patterns of particular species. Several blocks down Newbury Street is a 14″ plus caliper American Elm that appears to be growing in a no more than two foot square pit. That tree is tough. Elms in general are tough — one reason, aside from their obvious aesthetic appeal — that they were so successful as street trees for so long.
Honey locust is another tough tree, though they tend to be surface rooters once they’ve put on some growth, and that leads to the sidewalk-buckling problem. I agree that we need to up our game. Doing that would, to my mind, include educating people (storeowners, city officials, random pedestrians, dogwalkers) better about the value of trees in the city.