Broken windows theory has its share of criticism. In Tipping Point (or maybe it was one of his others, or freakonomics), they are able to connect the drop in crime rates with both the legalization of abortion and/or the banishment of leaded gasoline. Point being, it's nearly impossible to separate causality in sociological phenomenon.
It was Freakonomics that theorized that abortion was the cause of the drop in crime (which occurred nationwide as it was happening in NYC, though not to the same degree). Gladwell has debated with the authors of Freakonomics (primarily the economist Steven Levitt) about this.
Oakland sounds like a more permissive place that attracts scum. In NYC, they kick you out of the projects when you misbehave and scumbags end up migrating to smaller cities.
http://en.wikipedia.org/wiki/Broken_windows_theory#Criticism...