To make his point, Gladwell covers a variety of events and issues, including the arrest and subsequent death of Sandra Bland; British Prime Minister Neville Chamberlain's interactions with Adolf Hitler; the sex abuse scandal of Larry Nassar; the Cuban mole Ana Montes; the investment scandal of Bernie Madoff; the Jerry Sandusky child sex abuse scandal; the trial of Amanda Knox; the Brock Turner rape case; Sylvia Plath's death; and the Kansas City preventive patrol experiment.

[9][7] Gottlieb notes how Bernie Madoff, Jerry Sandusky, Ana Montes, and others deceived not only strangers, but also those familiar and close to them.

[9] Andrew Ferguson writes in The Atlantic that Gladwell does not define the word "stranger" in the book, and the definition varies according to the story being told.

[10] Tavris also criticizes a footnote that she says is "flat-out wrong", writing, "The idea that traumatic memories are repressed and can be retrieved only under the direction of therapy is—to say the least—controversial".

"[9] Tavris asserts that Gladwell's whole point is that we label people too quickly, even without knowing the whole picture; we think that we would be able to recognize evil when it stared us in the face, and how wrong we are in this assumption.

[12] Andrew Anthony of The Guardian is doubtful of the relationship between the various circumstances Gladwell draws comparisons between, still suggesting the book is "fascinating study of gullibility and the social necessity of trusting strangers".