The short-fingered vulgarian cometh: When Spy met Trump

When Donald Trump met Spy magazine

By Mark Ames , written on July 23, 2015

From The History Desk

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. —SPY, November 1987

I found a second reason to appreciate tech — the SPY magazine archives scanned and searchable in Google Books.

It couldn’t have come at a better time, now that Donald Trump is leading the GOP back to the White House, and the rest of humanity to End Times. (My first reason to thank tech, you might remember, is the online tobacco documents library that I wrote about recently—the open black box on the deadliest capitalist conspiracy ever and the Big Tobacco shills who played wingman to mass death-for-profit, from Malcolm Gladwell and Glenn Greenwald to UCLA Medical School and the American Civil Liberties Union.)

It’s hard to explain today what SPY meant when it appeared out of nowhere at the end of the 1980s, as the Reagan freeze was just starting to melt. There wasn’t much going on culturally by then—most of anti-commercial cultural energy went into music, into all the subspecies that 70s punk spawned, but that pretty much died out or devolved into kitsch by the time SPY appeared.

SPY was vicious and funny and smart — a fortress/safe zone for all the legions of pissed off, overeducated college grads with literary ambitions and a long list of personal grudges to work off... and bridges to burn. What made each new issue of SPY thrilling to read was the vicious satire—the way they went too far, gratuitously vicious, beyond the point of repetitiveness, to hit some very deserving targets.

SPY won my heart by relentlessly savaging what passed for the American literati in the Reagan Era: Bret Easton Ellis, Jay McInerney, Tama Janowitz — the triumvirate of the talentless, all that was loathsome, boring, affected and just plain wrong with American prose.

But SPY was also very local, a kind of provincial Manhattan highbrow hate-zine for insiders — so some of its targets meant nothing to me. It was through SPY that I first learned about Donald Trump. I couldn’t understand SPY’s relentless vicious targeting of Trump, why a sleazy real estate developer mattered so much — but like a good loyal SPY reader, I supported their hate 100%, the more gratuitous and vicious, the better.

What affected me most about SPY’s satire was its recklessness and irresponsibility, at least by the stuff-shirt standards of American prose. And even by contemporary standards of what passes for “biting satire” in this country. One of the problems I’ve always had with Jon Stewart and Colbert is the sense you get that they don’t really want to drive the targets of their comedy to ruin and dance on their graves. There’s something a bit too self-consciously responsible about their comedy, however brilliant and talented—a humanitarian, liberal impulse that they can always be friends with the targets of their satire, if they can all make a show of laughing at themselves and not taking themselves too seriously.

Spy vs Trump only reveals how fleeting and false even the bloodiest satire is against real cultural power in this country.

You never got the sense that SPY took its targets lightly or saw its satire as all a big joke, ha-ha-ha, we’re all friends at the end of the day bullshit. SPY was serious about its hate, in spite of its somewhat precious prep school surface prose. SPY wanted its loathsome celebrity targets destroyed, not merely roasted. And those who fell were not nobly pitied or helped back up with a gentlemanly hand; SPY shamelessly gloated over their fallen celebrity corpses and dragged them through the magazine’s central squares and back alleyways for all to have a mean vicious laugh at.

And of all the SPY celebrity villains, it was Donald Trump, the “short-fingered vulgarian,” they loathed most of all in those early years. Trump was also described as “Queens-born casino operator”; “ugly-cuff-link buff”; “well-fed condo hustler”; “joyless punk millionaire”; “employer-of-white-people”; “tiresome punk infidel”; “the wife-dumping Atlantic City strongman”; and I’m sure a dozen or more other descriptions I’ve missed in those glorious archives.

Looking back today, as Trump leads the polls to become the GOP nominee for president, it all makes a horrible kind of sense. Cultural Stagnation has hung over Campaign 2016 like a dark rainless cloud as we wait for the inevitable choices between two of the dreariest dynasties any empire ever produced. But it’s Trump—the dilapidated retread, bushy-eyebrowed, unkillable—who plays American Brezhnev in our Era Of Peak Stagnation.

The past few weeks, just about every media halfwit has been burning both ends of the zinger candle trying to nail Trump. But as the old SPY archives demonstrate, he’s not only loathsome, he’s also quite hard to kill. Reading through the back issues, you learn pretty much everything you need to know about the Donald—and you see the trajectory of hate, from somewhat marginal figure of derision in the early issues, to obsessive loathing, to dancing on his grave, to a kind of defeatist resignation when it becomes clear that in fact nothing can kill the Donald—and that in the end, as Old Man Lebowski might put it, “The bums at SPY lost! Condolences!”

So let’s begin at the beginning—the fall of 1986, when SPY first launched. The debut issue, October 1986, lists Trump in its “Ten Most Embarrassing New Yorkers” alongside Midge Decter, George Steinbrenner, Rex Reed, and the infamous Leona Helmsley. The idea is right, but the writing is pretty safe and limp by later SPY standards:

[F]orget just about everything concerning Donald Trump except the stupid things he says:

“It would take an hour and a half to learn everything there is to learn about missiles. . . . I think I know most of it anyway.”—On his desire to handle nuclear-non-proliferation negotiations for the United States.

“They weren’t even sculptures. They were stones with some engraving on them. They were nothing. Just junk.”—Trump’s rationale for destroying Ely Jacques Kahn’s art moderne frieze on the front of the old Bonwit Teller building.

“Electricians make a hundred and some odd dollars an hour. The concrete people just make fortunes. Laborers make hundreds of thousands of dollars a year.”

In the next issue, November 1986, SPY started getting a bit more serious—a smallish article on Trump real estate bullying and sleaze, relegated to one of the columns towards the back of the book, a sharpened six-paragraph boxcutter titled “Will Trump Get Spanked?” The article describes how Trump tried to bully and bury a respectable Manhattan law firm for the crime of successfully defending tenants in a Trump property from unlawful eviction. After losing the lawsuit, Trump launched a RICO civil suit against the winning law firm, using a law designed to dismantle violent mob organizations:

Trump essentially argued that the opposing lawyers were racketeers because they opposed him—that their intention to “prevent, frustrate and inhibit” him from making larger profits by evicting the tenants constituted “extortion.”
A New York federal court told Trump to get lost, dismissing his case.

Trump’s lawsuit so offended even Ed Meese’s Department of Justice that they tabled a new law restricting RICO civil suits only to those defendants actually convicted of criminal RICO racketeering crimes, while the courts considered sanctioning Trump’s company for violating federal rules of civil procedure. For SPY, this augured well:

Thanksgiving approaches. Where should gratitude be affixed? As far as we’re concerned, any setback encountered by casino operator Donald Trump is providential, always cause for merrymaking.

Later, SPY reported on some of Trump’s sleazy slum lord tactics used to try to evict his tenants from his 100 Central Park South property so that he could tear it down and build what’s now known as Trump Parc East:

In 1984 tenants refuse to move out of a building that well-fed condo hustler Donald Trump wants to tear down and replace with something a bit more, well, Trumpish. He tries to speed them on their way by filing lawsuits, eliminating services and letting the building get shabby. Next he disingenuously offers to let the city house homeless people in vacant apartments in the building.

Trump planned to pack his Central Park South building with homeless people to drive tenants out. But instead of placing homeless people in Trump’s building, the city offered to put Polish refugees there instead. Trump countered with some early immigrant-bashing, saying he’d only allow “people who live in America now, not refugees [from Communism].” Who knew that Trump’s patriotism was such that he preferred signing leases with red-blooded homeless Americans over Polish refugees from Soviet occupation, because after all, they’re all just a bunch of rapists and drug addicts.

A few years later, SPY debunked another Trump myth about his business acumen—how he was able to buy the $20 million Mar-a-Lago mansion estate for what Trump boasted was a quarter of that price—proof of his tough deal-making skills. In fact, Trump managed to buy the Palm Beach estate with only $2,812 dollars coming out of his own pocket, the rest—99.97% of the financing—coming from his murky tight relationship with Chase Manhattan Bank. This all came out in a lawsuit sparked by Trump himself, an incredibly stupid lawsuit that betrayed a baloney-brained thinking completely at odds with the entrepreneurial genius he’s sold the world. SPY explained:

[O]ne does not become a short-fingered casino operator by being easily satisfied. When the local tax assessor backhandedly confirmed what a fabulous deal Trump had negotiated by declaring the value of the property to be $11.5 million — 64 percent higher than the [$5 million] purchase price — Trump cried foul. He challenged the assessment in court, even though the additional taxes amount to a mere $81,525, less than what he spent last spring for newspaper ads supporting capital punishment. But what was no doubt an unintended consequence of the suit, which he did not win, was the glimpse of the Mar-a-Lago deal revealed in court papers, one that shows that the heroic account published in The Art of the Deal was exaggerated, if not simply false.

SPY had a local reporter for the Palm Beach Post annotate and correct Trump’s many boastful lies about the Mar-a-Lago purchase in his book, The Art of the Deal. Among the 16 falsehoods:

  • Trump: “Buying Mar-a-Lago was a great deal even though I bought it to live in, not as a real estate investment.” SPY: “In a deposition taken for his lawsuit against the county, Trump said his first offer on Mar-a-Lago was turned down by the [nonprofit] Post Foundation [which owned it] because he wanted to build 14 houses on the estate.”

  • Trump: “I first looked at Mar-a-Lago while vacationing in Palm Beach in 1982. Almost immediately I put in a bid of $15 million, and it was promptly rejected.” SPY: “Trump said he learned about Mar-a-Lago from an anonymous cabdriver. ‘I said, “What’s good around here that’s for sale?” He said, “Well, maybe Mar-a-Lago is for sale.”’ The cabbie, Trump noted, should have been a real estate agent. ‘He could have been a wealthy man today. That’s called the breaks, right?’”

  • Trump: “Almost immediately I put in a bid of $15 million, and it was promptly rejected.” SPY: “In fact, $9 least seven months later.”

  • Trump: “Finally, in late 1985, I put in a cash offer of $5 million.” SPY: “Trump got 99.97 percent financing on Mar-a-Lago from Chase Manhattan Bank, laying out only $2,812 of his own money as a down payment.”

The next year, 1987, the first full year of SPY, saw the magazine trying to play somewhat by the rules by laying off Trump for several issues. With few exceptions—speculation that Trump, “a casino-operating hustler,” was considering running for mayor of New York against Ed Koch, whom Trump publicly called a “moron” and his aides “jerks,” while Mayor Koch called Trump “greedy, greedy, greedy” and “piggy.” A SPY house ad featuring a swinging asshole in a coat and tie, very Trump-wannabe, pointing at the reader:

“These are the reasons I don’t read that magazine Spy:

SPY is new, and I don’t like new things.

It calls itself The New York Monthly.

It makes fun of Republicans.

It makes fun of Democrats.

It makes fun of Donald Trump

SPY names names, and that’s just not nice.”

In October, the magazine published its first “SPY 100 list”—“our annual census of the most annoying, alarming, and appalling people, places and things.” Placing #3 on the list: Donald Trump, with an “Inherent Loathsomeness” factor of 10 out of 10. (Others on the debut SPY 100 list: A.M. Rosenthal (#33), whose “misdeeds” include “his column; his column; his column”; “Superconductivity” (#72); and Amy Carter (#90).)  

By early 1988, SPY was battle-hardened, its satire more confident, meaner and smarter. And Trumpier.

The April 1988 issue, “Our Nice Guy Issue” is the first of many to feature The Donald on the cover, smiling sweetly, flashing a cheerful thumps-up, the lead header reading “DONALD TRUMP: A Heck of a Guy”. It features a head-to-head competition between Trump’s book The Art Of The Deal (“with former journalist Tony Schwartz”) versus artist Julian Schnabel’s CVJ: Nicknames of Maitre D’s & Other Excerpts from Life:

Which book is bigger? Hard to say: Trump’s has 246 superlative-crammed, first-person-pronoun-packed pages, to Schnabel’s high-school-yearbook-formatted, picture-extended 222 . . .
Among other things, the two books prove that in the right hands, aggressive pretension and aggressive lack of pretension can be equally horrible.

Setting snippets against each other, head-to-head, SPY reveals:


Schnabel: 15.3            Trump: 21.21


Schnabel: I paint paintings because I can’t get the experience in any other way but there are many more experiences that are equally satisfying to me...

Trump: I do it to do it. Deals are my art form. . . . I like making deals, preferably big deals. That’s how I get my kicks.


Trump: I now have in my will a clause describing the importance of that restrictive covenant [preventing Hyatt Hotels from opening a hotel in New York that would compete with the Trump-built Grand Hyatt], just on the chance one of my heirs happens not to be that smart.


Trump: In the second grade . . . I punched my music teacher because I didn’t think he knew anything about music. . . . I’m not proud of that, but it’s clear evidence that even early on I had a tendency to stand up and make my opinions known in a very forceful way.


Schnabel: For me art isn’t about self-expression.

Trump: Sometimes — not often, but sometimes — less is more.


Schnabel: What material is the stuff we are made of? In this Zone of Dust? A glimmer?

Trump: You’ve got to give it to [Judith Krantz]: how many authors have written three number-one best-selling books in a row?

When October rolled around and SPY released its second annual census of the 100 most annoying/appalling people/places/things, Trump dominated. He didn’t finish Number 1 on the list—that top honor fell to Al Sharpton, whose “Misdeeds” included “doesn’t vote or pay taxes (‘I want to know why I or any other black has to pay taxes’); wore a wire as a federal snitch”. But like a one-man Goldman Sachs, Trump dominated all the key spots on the SPY 100 list:

  1. Donald Trump, Candidate. Inherent Loathsomeness: 10. Misdeeds: Bought full-page ads in three major papers to present his crude, jingoistic views on foreign policy; said, “I’m not running for president, but if I did . . . I’d win.”
  1. Donald Trump, Acquirer.
  1. Donald Trump, Boxing Promoter. “Ringside introduction of the vile Trump clan lasted longer than the Tyson-Spinks fight.”
  1. Donald Trump, Author. Misdeeds: Trump: The Art of the Deal exhibits author’s bogus populism (“Perhaps the worst thing about rent control is that it stopped protecting the people who needed it most”), insight (Roy Cohn “was no Boy Scout”) and boundless respect for excellence (“I. M. Pei . . . often chooses the most expensive solution to a problem—and is virtually uncontrollable”); dictated book to former journalist—Tony Schwartz.
  1. Donald Trump, Fixer of Things We’d Almost Rather Leave Broken. “Invited irrational speculation on the part of the public that, just maybe, he was the solution to—rather than the cause of—any given nagging urban problem”.

But even better than Trump’s multi-placements on the SPY 100 List was one of those small little comic gems you’d always know you’d find in the magazine’s nooks and crannies. In a back-pages column, The Big Questions, Joe Queenan tracked down Rabbi Harold Kushner, the author of that nauseating Reagan-era best-seller, When Bad Things Happen to Good People, the real question good people demand an answer to: Why do good things happen to bad people?

All right, how about somebody who works 18 hours a day to amass huge sums of money but who seems too shallow to be capable of desperate unhappiness? Why is God giving Donald Trump a free ride? After systematically vulgarizing New York City, why did the Queens-born casino operator become a best-selling author too?

“I don’t know enough about Trump personally to make a definitive judgment on that,” said the rabbi. “But broadly speaking, there are two answers. One is that Donald Trump is an honest real estate developer who is very driven and knows how to play hardball but who has earned the money he gets just as much as Johnny Carson and Jim Rice have.” I mentioned that Jim Rice was having a dismal year and was a poor example. “Okay—Roger Clemens or Larry Bird. The other answer is, if Trump is an evil person, he will surely trip himself up at some point with his unhealthy appetites and at the very least suffer some sort of loss in the personal-development area. He will either be the Larry Bird of real estate or the Ivan Boesky.”

For the third annual SPY 100 List, Trump’s loathsomeness had reached such cosmic proportions that something big had to change in the loathsome-calculus to reflect this—Trump had essentially become the essence and DNA of all that was loathsome. So his name was taken off the list, and his Platonic Form became the list, as SPY explained,

In 1987 Donald Trump ranked No. 3. By last year he had begun to annoy, alarm and appall in so many different ways that he made the list five times (Nos. 10, 14, 21, 26 and 30). This year he has moved to another plane altogether. He has ceased to be a player and has instead become part of the playing field. Trump does not win a position on the list this year, but his ethos does, all over the place. We realized that he had caused, commented upon or in some more tangetial way had something to do with every single one of the entries on The SPY 100, and so a new category had to be created to speak to the overall Trump-relatedness of any given honoree. (In the revised formula T is for TrumpScore™, L is for Inherent Loathsomeness, M is for Misdeeds, F is for Mitigating Factors and B is for Bonus Points.

Samples of TrumpScores:

#3: LEONA HELMSLEY: Trump called her a “disgrace to humanity in general.”

#5: BATMANIA: Batman outgrossed even Ghostbusters II, a movie that spawned a music video in which Trump appears.

#35: GUNS, GUNS, GUNS: The Trump Princess [yacht] once belonged to arms dealer Adnan Khashoggi

#44: RONALD REAGAN: Trump has compared rival developers to Reagan—“people who talk a good game but don’t deliver.”

#62: LAWYERS GONE BAD: In his correspondence with SPY threatening legal action over an article about his wife that neither he nor his lawyers had seen, Donald Trump wrote “my attorneys are chomping [sic] at the bit” over SPY’s so-called “liable [sic] and extortion.”

By this time, as the SPY list made clear, the notoriously litigious Trump wanted the magazine dead. So badly, that he publicly predicted its death, and even gave a date. And so, as SPY liked to remind readers (and Trump) over and over, in September 1988 Trump “leaked” to Daily News gossip columnist Liz Smith that SPY was on the verge of bankruptcy and would be closed within a year. In a July 1989 SPY reminder, headlined “Chronicle of our Death Foretold: A SPY Public-Service Countdown,” they quote from Liz Smith’s column from a year earlier:

“My pal Donald Trump . . . said that SPY magazine is in trouble financially and will not be around much longer. I chided the handsome mogul, of whom I am very fond . . . that he should not indulge in wishful thinking. He said, ‘No, you’ll find this is true if you just investigate. I predict they won’t even be around in a year.”

Gosh, you gotta figure that’ll come back to haunt him...

In SPY’s final issue of the decade, December 1989, the short-fingered vulgarian did not disappoint. SPY quoted Trump telling reporters,

“If I were starting off today, I would love to be a well-educated black, because I believe they do have an actual advantage.”

Shortly afterwards, SPY reported, a local Manhattan temp agency, responding to a call from the Trump Organization for clerical workers, sent a rep to meet with a Trump executive. According to SPY,

the Trump executive made things simple: Don’t send us black temps, the executive explained. Some more astonishingly overt racism followed, but a spokeswoman for Trump denied to SPY that her boss has any such policy. Indeed, she added, “We have a new [black] gal [and] I think we have another one still with us.”

Ah, but there was more. SPY got vital intel on the secret to Donald Trump’s bizarre hair composition. Someone friendly with SPY who was invited to the SNL 15th anniversary show and after-party passed along exactly the sort of unsavory details that showed just how petty, vicious and low SPY was willing to go in their public war with the short-fingered vulgarian:

If you saw Saturday Night Live’s fifteenth-anniversary special, you know that Chevy Chase, walking through the audience during the opening, spilled popcorn on employer-of-white-people Donald Trump. And that Trump, hearing the laughter and appreciative applause (for Chase), forced a smile and pumped his arm in the air. But unless you attended the post-broadcast party in the Rainbow Room, you probably didn’t have the chance to notice a piece of popcorn still lodged, more than an hour later, in Trump’s hair, as one fellow partygoer did. The partygoer (high enough on the executive food chain to actually touch Trump) picked away the stray kernel and accidentally discovered Trump’s horrible hairstyling (and popcorn-adhering) secret: hair spray. A superabundance of it, so thickly applied that his hair has the texture of fur on a cheap stuffed animal.

In another section in which SPY reported on various celebrity book signings about town, a reporter who attended Trump’s signing event for “Trump The Game” at FAO Schwarz reported,

About 300 people have shown up, though later a spokesperson, accustomed to thinking like a Trump, will profess that “thousands” had attended. The author’s fans, including an unsettling number of balding men with ascots and silky pocket puffs, wait on a line that stretches through Mickey Mouse fashions and the Barbie boutique...

And then came 1990, and everything came to a head, so to speak. SPY was just getting warmed up in the 1980s. But it was in 1990 that Spy decided, as Bugs Bunny would say, “this means war.”

First, SPY triumphantly reported on the disaster that was the Trump Castle World Power Boat Championships in Atlantic City: “One death, three broken backs, one severe concussion and two other, slightly less serious injuries.”

In 20 years of New Jersey offshore racing, there had never been a fatality. Even as the entire power boat profession turned on Trump, he declared it a major success afterwards, and vowed to follow up by hosting the America’s Cup there. But perhaps the most shocking details were Trump’s own apparent excitement at how the stormy weather, while deadly for racers, was great for business:

As rain poured down in a violent storm, Trump said, “I hate to sound overly optimistic, but from a truly cynical financial standpoint [the relentless rain] makes it a better event for the Trump Castle. I just walked through the Castle and it’s booming in there.”

The rains were so torrential that some racing events had to be put off, but on the final day, Trump made everyone get back in the water and race. And that’s when the blood started to flow:

Yes-X-Press of Saddle River, New Jersey, took the lead briefly, before being flipped and then crushed like a beer can by a wave; both driver and throttleman were hospitalized. Farther out at sea, a mile from the starting line and the “world’s largest video screen” (erected by Trump to serve a projected 1 million spectators, most of whom never materialized), the boat Team Skater bounced off a wave, landed nose-first and barrel-rolled, landing upright— killing the driver, Kevin Brown, instantly.

At the awards ceremony—which Trump wisely failed to attend, and during which his name was booed—there was no official mention of the death...

No fan of dreary postmortems, Donald Trump was focused on the future, envisioning far more prestigious maritime catastrophes. Of his plans to bring the America’s Cup race to New Jersey, Trump recently told an interviewer, “From what I understand, the waters off Atlantic City are virtually perfect.”

Note: the February 1990 issue was the first time SPY described him as “joyless punk millionaire Donald Trump.”

Two months later, SPY added “tireless punk infidel” and “The wife-dumping Atlantic City strongman” to its ever-more-precise catalogue of descriptions. And with the divorce of Donald and Ivana Trump making news, SPY announced it was holding a “Nationwide Search for the New Mrs. Donald Trump!” complete with cut-out prenuptial contract:

Calling all singles and swingles: are you so much better than a “10” you can’t believe it? If so, it’s time to set your love fancies free in the most romantic magazine contest ever! SPY is seeking heartfelt essays of 100 words or less on the topic “Why I Should Be the New Mrs. Donald Trump.” Anyone of either sex may enter, just as long as he or she is not Marla Maples or an employee of SPY magazine. Each of the three winners — to be chosen on an entirely subjective basis— will receive a SPY T-shirt, SPY sunglasses and an unautographed copy of Trump’s The Art of the Deal (said to be rarer than signed copies!) Send your entry to It’s Lonely at the Top c/o SPY, the SPY Building, 5 Union Square West, New York, NY 10003
What’s the catch? Possibly the biggest, richest, shortest-fingered catch in town! That’s right: all entries will be forwarded via fax machine to Mr. Donald Trump at the Trump Organization. So don’t forget to include your phone number, a signed copy of the contract at right and a photograph suitable for electronic transmission. (No nudity, please. Okay, well . . . a little).

Now you see what I mean about going too far. No one has had the balls to do it since SPY. We did it at The eXile—we went a lot further in fact, erring way too far on the side of “too far”—but to do it, we had to publish in the capital of a collapsed empire, in the deadliest and most violent place on earth...

What is more impressive and amazing — speaking as a connoisseur of satire, hate and literary vengeance — is that as Trump’s fortunes collapsed in 1990, with creditors pouncing and debt payments missed and his ownership stakes taken away before his eyes, SPY avoided falling into the fatal ol’ trap of pitying the sociopath at his most vulnerable, and instead sent in the cavalry to cut Trump down at his weakest moment. That is commitment; that is something you’ll never find today.

It came in the August 1990 issue, SPY’s greatest of all, featuring a bawling oversized Trump head on a child’s body in prep school uniform, with the headline:

“WA-A-A-A-H! Little Donald—Unhappy at Last”
“Trump’s Final Days, Page 50”

SPY managed to both gratuitously drive its satirical stake in Trump’s heart—then pull it out, twist it, drive it in again, and wiggle it around…  while at the same time presenting Trump’s fall from grace in a larger cultural context of the collapse of the entire Reagan Era. It was as if, for that brief glorious moment, SPY had won — and, vicariously, so had SPY’s readers, those multitudes of thwarted celebrity geniuses and wasted talents that we were.

SPY had a local reporter for the Palm Beach Post annotate and correct Trump’s many boastful lies about the Mar-a-Lago purchase.

The context was the feature story on “America’s greatest sore losers—including Richard Nixon, Spike Lee, Several Democratic presidential candidates, America itself, and, inevitably, Donald J. Trump”:

You hear it everywhere you go—whining, complaining, crying foul. An epidemic of aggressive self-pity is gripping America, and nobody seems to mind.
Time was when people were brought up to be good losers. The defeated Little League team was required to give the winners a cheer. The first runner-up in the Miss America pageant was supposed to embrace the winner the moment she won. . . . Being a good loser was part of being a good American, especially back when America invariably won.

The first part of the story was a dissection of the Sore-Loser ecosystem and fauna:

SORE-LOSER HANGOUTS: The lecture circuit, Meet The Press, The John F. Kennedy School of Government

SORE-LOSER ARCHETYPES: Yahweh, Richard III, Germany, Yosemite Sam

SORE-LOSER PASTIMES: Having your screen credit removed; “Writing” your “memoirs”; Rumor-mongering; Litigating; Press-bashing; Wearing black

SORE-LOSERS’ WORDS TO LIVE BY: Let’s make it best of three. Why don’t the media focus on the positive things? The dream will never die. It was a moral victory. We live in a commercial/racist/sexist/fascist society. I’m going to take some time off to write. This is what I get for refusing to sell out. These kids have worked so hard all year—and then they have it ruined by the goddamned officials.

The article describes six different types of “Sore Losers” including:


Grandstanding Sore Losers try to transform the personal setback into a cause. For example, when Donald Trump earlier this year resisted his wife’s attempt to gain a more lucrative settlement, he cited an obligation to defend the principle of a contract. . . . Spike Lee suggested that sex, lies and videotape won the 1989 Cannes Film Festival’s Palme d’Or because the film’s director was white. Lee said that if he ever saw German director Wim Wenders, who chaired the Cannes jury, he would be “waiting for his ass.”


In 1988, Sore Loser King-in-the-making Donald Trump replied to a column by architecture critic Paul Goldberger with a letter. “The New York Times should not have allowed Paul Goldberger, whom I have criticized openly in my book and elsewhere as being totally lacking in taste, to critique Donald Trump and Trump: The Art of the Deal” was the missive’s solemn opening.

And then came the coup de grace: an eight-page spread of fake newspaper clippings from a time machine, tracing the sad decline and disgrace of Donald Trump from 1990 – 1996. Headlined “A Casino Too Far: Pages from the Donald J. Trump Scrapbook, 1990-96,” it stands as quite possibly the funniest and most savage eight pages of satire ever put to glossy print in this country:

“In the previous installment of the Donald J. Trump Scrapbook the following events transpired: Trump attempted to slough off his glamorous, reconditioned wife, Ivana, in favor of young, pliable nineties edition Marla Maples; he opened the horrifically kitschy and monumentally leveraged Taj Mahal casino; he saw his net worth devalued by 70 percent in Forbes magazine; he floated the idea of selling his airline and other assets in what he claimed was an effort to become a “king of cash”; and he became the subject of speculation about his ability to service the $3.2 billion debt that is the basis of his empire. Now the saga continues.”

The first page begins with a funny-because-it’s-so-authentic fake New York Times Magazine clipping celebrating Trump’s ability to meet his creditors’ payments, dated September 1990, or just one month into the future. Headlined, “Weathering the Storm: How Donald Trump Met a Looming Payment to His Bondholders Amid a Swirl of Rumors About His Solvency,” the article strikes exactly the sort of patronizing, forgiving (and prototypically worshipful) tone that SPY not only mocks, but violently rejects:

He looks composed now, relaxed, not at all like a man who just three months ago danced around the lip of a volcano of debt and lived to tell the tale. . . . Now he seems almost gentle, not the sort of man who would call his father, Fred, at 3:30 on the morning of the day a $47 million payment to bondholders was due and plead with him to increase the debt on his Queens real estate properties in order to help his son raise the last bit of cash to make the payment. “Goddamn it, Dad, you’ll be a nobody,” Trump reportedly screamed into the phone. “I’m smart, I’ll survive, but what’s Bob [Donald’s brother] going to do? Move back in with you and Mom? Wash windshields at the Lincoln Tunnel? Now, I’m sending over a lawyer and a guy from First Jersey, Dad. And you’ve got to sign the damn papers!”
“I guess it was a pretty intense moment,” chuckles the 44-year-old developer...

After twisting the knife further, with a fake Wall Street Journal clipping on Trump’s inability to sell a single asset even at a loss, comes this New York Times clipping dated the day after Christmas, 1990:


“A Christmas Miracle” Reported by Police: No Injuries

A series of explosions wracked the hangars of the Trump Shuttle in New York, Washington and Boston yesterday morning. The explosions, which went off simultaneously at around 8:15 on Christmas morning, ignited fires that burned out of control until early afternoon.

The entire fleet of 21 727’s, which had been grounded for the holiday, was destroyed.

Naturally, Trump staged it. And naturally, while playing anonymous terrorist, he contacted a top newspaper gossip columnist posing as a terrorist leader, because terrorists naturally seek out celebrity gossip columnists:

Moments after the explosions, a columnist for the New York Post, Cindy Adams, received an anonymous telephone call from a man identifying himself only as a member of a “top terrorist organization in Asia,” who claimed responsibility for setting off the explosions.

According to authorities, the man told Adams that the explosions were meant as a reply to Donald J. Trump, the airline’s owner, who had on Friday of last week placed full-page advertisements in six major American newspapers calling on President Bush to take a harder line in trade talks with Japan. “We knew the amazing amount of influence Trump has on the President,” the caller reportedly told Adams.

“Obviously I’m just devastated,” said Mr. Trump in a telephone interview. “The Trump Shuttle was a jewel. Everybody wanted to fly it. I was probably going to sell it next week to this German group for $670 million or $680 million, an unbelievable profit. Fortunately, we’re fully insured—in fact, we got some additional coverage right after Thanksgiving, thank God.”

A year later, and Trump has been forced to disgorge the insurance money to his creditors, starting with his ex-wife Ivana Trump—who, future-Liz-Smith writes, has been seen partying and dating everyone from Keith Hernandez to Mike Tyson, “who the morning after his night out with Ivana in December was said to have growled, ‘Tell Trump we’re even.’ Whatever that means. . . .”

As more Trump properties collapse in value, the gossip rags report that Trump has been seen dating a series of elderly heiresses, including Basia Johnson (heir to the Johnson & Johnson fortune), Bubbles Rothermere, and Doris Duke— just long enough “to close on a condo at Trump Tower.” He raises some more cash by allowing a developer to build a shopping mall/condominium complex on his Palm Beach Island estate. Meanwhile, his ex-wife Ivana Trump gets elected to the Czech parliament and becomes Vaclav Havel’s lover.

By the end of 1992, the Wall Street Journal runs an article on Trump hiding from phone calls from jilted Polish government partners. Featuring a bloated, double-chinned, Trump in the trademark WSJ stipple drawing hedcut style:

Where’s Trump?

WARSAW, Poland — Every day, on his way to work, Tadeuz Michnik passes the big empty lot where one of the cornerstones of his nation’s economic recovery is supposed to be laid. And every day Tadeuz Michnik sighs, goes into his office and places a phone call to America that he knows will not be accepted or returned.

Tadeuz Michnik is Poland’s minister of Trade and Tourism. The man he is calling is Donald Trump. Two years after he gave Trump Casino Enterprises a $55 million cash down payment to build a complex of hotels, shops and gambling casinos in Warsaw, no progress has been made toward ground-breaking. “I’m a patient man,” says Mr. Michnik. “President Walesa is a patient man, and the Polish people are a patient people. But I’m beginning to get a little tired of being ignored.”

“They’ve been patient? I’ve been patient,” Mr. Trump replied from his office in New York. “Did you ever try to get quality marble in Warsaw? It’s pathetic.”

By 1993, the end is nigh: Trump files for Chapter 11. Marla Maples leaves him for the aged corpse-like chairman emeritus of Sony, Akio Morita. And his nine-year-old son, Eric Trump, is arrested on 173rd Street in possession of three stolen Blaupunkt car stereos at a notorious fencing operation run by a criminal known as Sweet Pea. “I did it to help my dad. He’s been having some trouble lately,” the nine-year-old boy reportedly tells police.

Trump’s artistic career takes a dive as well. His new book, “Trump: Surviving at the Top” flops; a video in 1993, “Donald Trump’s Guide to Winning at Bankruptcy” becomes a “camp classic” on Wall Street, with this advice from Trump: “Debt is like a woman—it’s fun, you can’t live without it, but don’t let it start making decisions for you.”

By 1995, Trump finally finds himself back on his beloved 282-foot Trump Princess yacht, only now it’s owned by a pet food magnate who hired Trump to run his customer relations department, and to keep the yacht guests entertained.

Ever the entrepreneur, Trump hawks men’s grooming products in the back pages of sleazy tabloids, a package deal for $19.95. He’s gained about a hundred pounds, and looks like Jiminy Glick just released from Riker’s.


“When I was going around the world in my giant yacht, or negotiating incredible deals, or running billion-dollar corporations, I always thought that my biggest asset was LOOKING GOOD. Now you too can look like a billionaire, with my new line of grooming products—Hair Spray, Mousse, Gel and Tint.”

TRUMP: The Art of Fine Grooming”

Finally, at the end of the spread, an incredibly prescient prediction: The joke is that Trump is returning to American culture, as the co-star of his own reality TV show, “Lunch With Ivana and Me.” He’s morbidly obese, in suspenders and comb-over, looking grim and humbled—exactly how SPY wants their defeated bully to look under glass, with a pin stuck into his thorax:

After The Hoopla, Trump Is Serene

New Yorkers who remember Donald Trump from his heyday would be surprised at the way he seems today. He is older, to be sure, and heavier, and his hairline is in full retreat, but those superficial features are not what command attention. What is striking is the change in behavior. Gone is the brash tyro, the swaggering tough guy. In his place is an amiable, somewhat unpolished charmer who is just the sort of person with whom you wouldn’t mind lingering over lunch.

Mr. Trump readily attributes the success of the show to his wife. “Channel 9 was all set to give her her own show. And Ivana said, ‘No, let’s get The Donald involved. I don’t want to do it without The Donald.’ I wasn’t doing much except liquidating my grooming-products corporation and doing a little consulting for the Sultan of Brunei—there’s a guy who knows the meaning of loyalty. When Ivana called, I thought, ‘Why not?’ After we taped the first show, I asked her out for coffee. I felt the old feelings. And, you know, she did too.”

Does Mr. Trump miss his glory days as a billionaire mover and shaker? “Sometimes I walk down Fifth Avenue and see Trump Tow—sorry, Geffen Tower, and I see how well The Plaza is doing under Yoko, and I feel angry that all that was taken from me. But what’s done is done....”

And that was it, the high-water mark for SPY, and for American satirical journalism. We all know what happens here. Trump comes back, stays thin, remarries a few dozen more times, and now is set to become the leader of the world’s only superpower.

And Spy goes out of business in 1997. Trump makes a few more appearances after that August 1990 issue. He ranks as #3 in the end of the year SPY 100 List, but all SPY can do in its description is gloat nervously: “Tell us we’re dreaming . . . Somebody pinch us.” It’s as if they knew it couldn’t last. Trump’s name largely disappears from the magazine, until the SPY 100 List shocker in 1996, when “The Return of the Donald” rockets to the top of the list. But it’s not funny anymore; it only reveals how fleeting and false even the bloodiest satire is against real cultural power in this country.

The good guys can’t possibly win. In this country, as Queenan complained to the rabbi, good things happen to bad people. And Donald Trump is having the best moment of his life—polling atop every politician in his party to become the next president of the United States of America.