I recently finished Malcolm Gladwell's New Yorker piece on David vs Goliath situations and I had the same beefs that a lot of readers seem to have had. Suffice it to say that the piece is structured around a really flimsy basketball analogy.
I just saw Ezra Klein's wrap up though and I definitely agree with his bottom line on Gladwell:
But Gladwell isn't an academic and he's not a traditional reporter. Insofar as he has a beat, it's modern fables. Stories with a point. He's like Aesop for the corporate class. To wit, the grasshopper isn't really a lazy insect. But then, the point of that story is the importance of hard work, not the characteristics of different bugs. And it's true that hard work is important. Similarly, full court press doesn't guarantee victory for weak basketball teams. But the point of that story is that weak agents need asymmetric tactics, which is also true. You get this in his books, too. Gladwell's core competency is finding fun stories that illustrate interesting -- and even true! -- concepts. It can be a bit precious and, in terms of the stories, occasionally wrong. But it lets him explore useful theories in a readable way. If you want to attack the work, you really need to go after the legitimacy of the basic theories. Questioning the stories doesn't get you very far.
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