Developed by James Wilson and George Kelling, broken windows theory is a criminological theory that explains the proliferation of crime by pointing to the decrepitude of the urban environment. Graffiti or visible signs of lawlessness act as signs of permission for more crimes to be committed and contribute to an environment of anarchy. Gladwell discusses broken windows theory as a prime example of The Power of Context: Small changes in social and environmental contexts can lead to unpredictable and massive outcomes. Gladwell argues that efforts to clean up urban environments and prosecute petty crimes can reduce overall crime. Rudy Giuliani brought practices based in broken windows theory to his governance of New York City in the 1990s. This led to increased arrests for offenses such as public urination, public intoxication, and squeegeeing at intersections. Critics point out that there is a lack of empirical evidence to support the effectiveness of these approaches and that they disproportionately impact Black and Latino populations.

Connectors are one of the three groups of special people, alongside Mavens and Salesmen, who make up Gladwell’s Law of the Few. These are the three agents of change in social epidemics. Connectors love to build up a portfolio of acquaintances and to introduce strangers to each other.