How the Original Insult War With Donald Trump Was Waged

It’s been the question of the summer (especially for Jeb Bush): How do you get under Donald Trump's skin, force him off his game? How do you go negative on a candidate who seems impervious to argument or insult, for whom the word “gaffe” has no meaning? One possible model for waging total war on the current GOP front-runner can be found in the archives of Spy magazine (available on Google Books), founded in 1987 by Kurt Andersen and Vanity Fair editor Graydon Carter, along with executive editor Susan Morrison, now articles editor at The New Yorker, to satirize the excesses of 1980s culture. “There were a lot of fantastic targets in the mid-eighties, all those newly rich Wall Street characters,” Morrison remembers, “but none of them were as bombastic or cartoonish as Donald Trump.”

Especially in its first few years, Trump was a constant target, assaulted with a barrage of insults and sobriquets—the most popular being “short-fingered-vulgarian.”