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.”

The Donald J. Trump Insult Index

Other miscellaneous insulting mentions

1. In the November 1987 issue, in an article about the following year's presidential election:

“Please, God, let him run. If Donald Trump runs for president, God, we promise we will never make fun of the pope again. Or Pat Robertson. Well, the pope, anyway.”

Layout from the January-February 1988 issue.
Layout from the January-February 1988 issue.
Courtesy Spy magazine

2. The April 1988 issue featured a fake ad for Trump’s book Trump: The Art of the Deal, written by “short-fingered vulgarian Donald J. Trump with former journalist Tony Schwartz” and on its:

 “12th Printing! Over 700,000 Copies!* … *Thousands of them bought by the ‘author’!”

A fake ad for “The Art of the Deal.”
A fake ad for “The Art of the Deal.”
Courtesy Spy magazine

3. In the April 1990 issue, the magazine launched a “Nationwide Search for the New Mrs. Donald Trump,” under the headline:

“White Whine, Walking on the Beach, Stacked Blonds Who Know How to Keep Their Mouths Shut …”

The cover of the May 1989 issue.
The cover of the May 1989 issue.
Courtesy Spy magazine

4. In the February 1991 issue, Spy printed a “Donald Trump Sign-Language Translation Guide” with the following gestures:

‘airplane,’ ‘braggart,’ ‘decorator,’ ‘grab,’ ‘I,’ ‘magician,’ ‘milk,’ ‘want’ and ‘worthless’

Trump’s body language, decoded.
Trump’s body language, decoded.
Courtesy Spy magazine

He also consistently topped their rankings

Trump was frequently given pride of place in Spy’s worst-in-New York and worst-in-America rankings, chief among them the so-called Spy 100 list—“The Most Annoying, Alarming and Appalling People, Places and Things”—not to mention in richly reported pieces about, for instance, his then-wife Ivana, and the state of his finances.

Exactly how did he qualify?

  • “Didn't promise he'd never run for office.” (1987 list)
  • “Bought full-page ads in three major papers to present his crude, jingoistic views on foreign policy.” (1988)
  • “Accepted the attentions of both Democrats and Republicans and incited Democratic leaders in particular to humiliatingly fawn over him.” (1988)
  • “Said 'I'm not running for president, but if I did… I'd win.'” (1988)
  • “Bought Plaza.” (1988)
  • “Bought gold-coated yacht Trump Princess.” (1988)
  • “Trump—whose military service doesn't extend beyond his teenage years at the New York Military Academy—was selected to lead the largest Veterans Day parade in New York's history after he donated over $100,000 to the parade. Quoth Trump: 'Marching with the military, politicians, and the president will be a lot of fun.’” (1995)
  • “Called Rep. Jerrold Nadler fat and stupid after he vowed to block Trump's proposed rerouting of the West Side Highway. After Nadler successfully got Congress to block federal funding to move the highway, Trump announced that he never wanted the road moved anyway and crowed, ‘Jerry Nadler fell right into my trap.’ Later claimed he had called Nadler ‘fat’ out of concern for his health: ‘I did it for a reason. I really feel that whatever can inspire him to go out and lose that tremendous amount of weight should be done. To be honest with you, he’s a walking time bomb, and if I can convince him to put himself, not in great shape, but in reasonable shape, I’m doing a great service to him and his family.’” (1995)
  • “Finagled an op-ed piece in the New York Times entitled: ‘What My Ego Wants, My Ego Gets’” (1995)

There were some “mitigating factors,” however

  • “Didn’t run for office.” (1987) (Note: Just a few months later, in the January-February 1988 issueSpy published a poll conducted by Penn + Schoen Associates that found that “one in 25 Americans wishes Donald Trump were running for president.”)
  • “Time spent stirring campaign rumors was time not spent planning building projects.” (1988)
  • “Negotiating to keep U.S. Open tennis in Flushing Meadow.” (1988)
  • “Trump waited until his back was absolutely against the wall before blaming his financial troubles on three Trump Organization executives killed in a helicopter crash in 1989.” (1990)
  • “Lost control of Central Park’s Wollman Rink to two former hot dog vendors.” (1995)

Did all this scathing attention bother him? It seemed to. He told Liz Smith in 1998 that Spy “won't even be around in a year.” Every issue from December 1988 through October 1989, the magazine re-published that snippet as a countdown to its own demise. The magazine ultimately survived nearly nine more years. “Unlike a lot of people that we wrote about, who would say, 'Oh, I never read that rag,' Trump read it, and he engaged,” former Spy editor Susan Morrison says. “He made it like a volleying sport. It was so fun to poke at him. It was like bear-baiting because he would respond and write us letters and call us losers. He was the gift that kept on giving.” (Despite threats of litigation, Trump never sued the magazine, according to Morrison.) 

And although more than 20 years have passed since the heyday of the Spy-Trump war of words, the evidence suggests that Trump still hasn't completely forgotten his adversary. On Jan. 14 of this year, one week after the deadly attacks on the Paris offices of satirical newspaper Charlie Hebdo and nearly 17 years after Spy published its last issue, Trump tweeted that Charlie Hebdo “reminds me of the ‘satirical’ rag magazine Spy that was very dishonest and nasty and went bankrupt.”

The cover of the August 1990 issue.
The cover of the August 1990 issue.
Courtesy Spy magazine

Donald Trump: Fodder for no fewer than 18 Spy lists

  1. “The Ten Most Embarrassing New Yorkers” (October 1986) (Note: The short write-up on Trump appears to run off the page, perhaps a sign of teething problems for the new publication's layout department. Not so, says Morrison, now articles editor at The New Yorker, who explains that this was a deliberate design decision to suggest that “a column could not contain all the embarrassing things about Trump.”)
  2. List of famous New Yorkers with a gun permit. (October 1986
  3. “Tall Men Who Behave Like Runts" (June 1987)
  4. “King Kong vs. Godzilla" (October 1987), a list of public fights from the previous year with Trump paired off against then-New York Mayor Ed Koch.
  5. “Smersh and Spectre Overlords and Various Other Bond Villains” (October 1988)
  6. “The Feud Chain” (November 1988), highlighting Trump's beef with Ed Koch, Merv Griffin, and Paul Goldberger.
  7. “Future Feuds… We Give Them Ten Years” (November 1988), pitting Trump against Alexander Cooper and Tony Schwartz.
  8. “Eighties Phenomena With a Curiously Seventies Feel” (December 1988), alongside diet Coke, Tommy Hilfiger and minivans.
  9. “Separated at Birth?”, a look-a-like feature where Trump is paired up with “the police sketch of Son of Sam” (March 1989) and “puffy-faced still-dead Elvis” (March-April 1996).
  10. “Hedging Their Bets” (May 1989), a roundup of donors to the campaigns of various candidates seeking to unseat then-New York Mayor Ed Koch.
  11. “The Great Mephistopheleses of Our Time” (June 1989),  alongside Mike Milken, Andy Warhol, and George Steinbrenner (Note: Former Spy editor Susan Morrison points out that this issue's cover—with tagline “Let's Make a Deal With the Devil”—depicts “Elvis Costello dressed as the devil in a business suit and he’s holding a card out in a Trumpian way, and the phone number on the card is the phone number for Trump Tower.”
  12. “The Famous People America (Sometimes Unaccountably) Likes Best” (January 1990), which placed Trump tied with 116 other people in 55th place, according to the Spy National Celebrity Survey.
  13. “Who Is America's Cheapest Zillionaire?” (July 1990), a Spy experiment where the magazine set up a fake company (the National Refund Clearinghouse) and sent “58 well-known, well-heeled Americans” fake refund checks in the values of $1.11, $0.64, and $0.13. Only Trump and Adnan Khashoggi (“arms dealer and Imelda Marcos codefendant”) deposited all three checks.
  14. “Sore Winners” (August 1990), alongside Marlon Brando and Ed Koch.
  15. “The SPY Tote Board" (July 1990), with Trump in first place, mentioned once every 25.6 pages. 
  16. “Twiggy, Can You Spare a Dime" (March 1991), about rags-to-riches stories and in which Trump is ranked as the least “rags” of the bunch, having started out with $200,000 (although “most of it was tied up in buildings”).
  17. “Remembrance of Everything Past: Who and What Are Stuck in Which Bygone Eras” (Nov. 1991), with Trump stuck in the 1970s alongside Woody Allen, the New York Knicks, organized feminism, and Newsweek.
  18. “Neither Rain nor Snow nor Dead of Career…” (July-August 1992), a Spy photo experiment in which the magazine sent four incompletely addressed postcards to 58 celebrities. In Trump's case, all four were delivered and responses received.
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