Malcolm Gladwell is a great writer, and the ideas he presents should not be ignored. In this book Gladwell tackles the idea of underdogs in a broad and detailed examination. The basic thesis for the book is that underdogs can win when they do the unexpected and the things that others do not think they will do. He presents many examples, from the book’s names sakes to a group of rich, white girls that win basketball games of far superior players by using a true full court press. I was reminded, as a boxing fan, of the countless upsets that I’ve seen over the years. Ali breaking all convention by urging the huge Foreman to keep hitting him (the legendary Rope-a-dope). Holyfield telling everyone that he was going to fight Tyson on the inside, and then doing just that and eliminating Tyson’s devastating lunging punches. I could go on for hours naming different strategies boxers have used to deceive or confuse their opponents and pull off upsets. But for every story like that there are thousands more of the people that get in there and do what is expected and get obliterated as expected.
I read this book with a different perspective in mind though. I was looking at it in regards to Donald Trump. Trump is the political outsider entering a race that he refuses to follow the unspoken rules. He won the primary by being that guy. By being the least presidential candidate in history, Trump put himself in a position to make a real run at the White House. How did he do it? By talking about his penis size, by insulting women, interrupting his counterparts, using a first grade vocabulary except when making it PG13, and by representing himself as the worst of us rather than the best. It was a strategy nobody was prepared for and as the polls come in and he has narrowed it to a coin toss, this strategy has worked. People are surprised, yet most people agree with H.L. Mencken: “Nobody ever went broke underestimating the intelligence of the American public.”