In one arc, Gladwell cites various seeming afflictions that may in fact have significantly contributed to success, linking dyslexia with the high-flying career of lawyer David Boies, and the loss of a parent at an early age with the exceptional research work of oncologist Emil "Jay" Freireich.

Other examples include: Vivek Ranadive, and a middle school girls' basketball team in Redwood City; Teresa DeBrito, and the impact of class size regulations; Caroline Sacks, and choosing between going to a top-tier college or a second-tier college; David Boies and how he still has a great career despite having or perhaps because of his dyslexia or a desirable difficulty; Jay Freireich and his cancer research, London bombings in World War II, and the effect of "remote misses" on the city's morale and a person's courage; activist Wyatt Walker and how he and Martin Luther King Jr. were able to make the Birmingham riot of 1963 a historically significant event in the civil rights movement using Brer Rabbit-like tactics; Rosemary Lawlor and how the Northern Irish police's reaction to religious riots in Belfast in 1969 led to a 30-year conflict called The Troubles, and contrasting this to how a police officer in New York City created a program that connected with troubled youths and their families; how Mike Reynolds' reaction to a family member being murdered led to the California Three-strikes law and how Wilma Derksen's reaction led to a completely different result; and André Trocmé, a pastor in a small town in the French mountains Le Chambon-sur-Lignon that stood up to the Nazi regime and harbored Jewish refugees.

Janet Maslin quipped, "As usual, Mr. Gladwell's science is convenient", and she concludes that "the book's middle section is its messiest", where the author attempts to link the experiences of famous dyslexics such as Brian Grazer and David Boies.

"[7] The New Republic reinforced this critique, calling the book less insightful than a Chinese fortune cookie and topping the review with the headline "Malcolm Gladwell Is America's Best-Paid Fairy-Tale Writer".

"[9] "To read David and Goliath is to suffer the discomfort of watching a formidably intelligent author flailing—by citing all manner of social-scientific studies and battering us with charts and tables and graphs—to prove something that no one would disagree with in the first place", wrote Craig Seligman for Bloomberg News.