In April 1988, Spy magazine put Donald Trump — then New York’s rising realtor and tower builder – on its cover. He was shown in a smiling, “thumbs-up” Trumpian pose, having by then made a name for himself with, among other properties, the Trump Tower on Fifth Avenue. Spy magazine’s cover, however, was followed by a second inside cover, this one showing Trump taking a fall. Spy, in fact, had a long-running bit of jab-and-spoof with Trump, all well before his more loftier positions, yet prescient in its warnings.
![]() Donald Trump on the cover of Spy magazine, April 1988 - billed in a story list as, “A Heck of A Guy.” |
![]() A second, inside cover of Spy magazine’s April 1988 edition has Trump taking a fall – and more inside. |
Based in New York City, Spy was a satirical monthly magazine published from 1986 to 1998. Co-founded by editors Graydon Carter and Kurt Andersen, the magazine specialized in irreverent and satirical pieces targeting the American media and entertainment industries, often mocking high society and prominent celebrities and other public figures, skewering their pretensions, exposing their corruption and foibles. Trump was among the targets, noted in parody pieces that portrayed him as a self-obsessed real estate developer, among other things. The April 1988 edition also included a fake book publishing ad for Trump’s then popular book, The Art of the Deal, as shown below.

This fake publisher ad for Donald Trump’s popular book, “The Art Of The Deal,” which appeared in Spy magazine's April 1988 edition, was preceded by an editor's notation at the top of the ad explaining that it wasn’t a real ad.
The ad had the polished look and layout of a real ad, with the names of then prominently-known leaders from literature and the media offering blurbs credited to, for example: Jonathan Yardly of The Washington Post, Publishers Weekly, The New York Times Book Review, Michael Kingsley of The New Republic.
The gag blurbs touted the book as “boastful;” “a public relations sell from the first page to the last;” and, an “exercise in self congratulation” – in fact, all charges and critiques that some Donald Trump critics then, and more later, would actually hold of Trump and his books.
At the base of the ad, an inset of The Art of the Deal book was shown, with descriptive by-line that read: “by Short-Fingered Vulgarian Donald J. Trump with Former Journalist Tony Schwartz.” The Random House logo followed below that, with a claim the book was then in its “12th Printing! Over 700,000 Copies!”, followed by an asterisk that explained in fine print, *“Thousands of them bought by the ‘author’.”
Trump’s book, in any case, was a real success. It had a first printing of 150,000 copies would spend 51 weeks on the bestseller list, with reports indicating it had sold over one million copies within its first few years. By the time of a 2016 investigation, total lifetime sales for the book were placed at roughly 1.1 million copies. While Trump would claim he wrote the book, Tony Schwartz actually wrote it. And former Random House head Howard Kaminsky, the book’s publisher, also noted Schwartz as author, adding, “Trump didn’t write a postcard for us!” Schwartz later regretted writing the book, and also suggested The Art of The Deal be “recategorized as fiction.”
But one of the Spy descriptors used in the fake book ad would live well beyond its 1988 use.
“Short-Fingered Vulgarian”
The author line beneath the book title at the bottom of the fake ad, used the phrase, “short-fingered vulgarian” for author Donald J. Trump. That description was used repeatedly by Spy in other Trump stories, and also by other critics and competitors as Trump later entered the presidential sweepstakes.
In a March 2016 NPR / Morning Edition radio interview with then former Spy co-editors Kurt Andersen and Graydon Carter, coming at a time when Trump was making his first run at the Republican presidential primaries. But Andersen and Carter explained to Morning Edition that for Spy magazine, Trump – then a rising outsider come to Manhattan – “epitomized so much of the sudden ostentation” of New York. In their view, self-promoting Trump embodied the brashness, the ostentation, the vulgarity of New York in the ’80s. And so, there was no question that he would be fair game for Spy’s special brand of barb-and-pique.

Donald Trump shows off the size of his hands at a Repub-lican presidential debate in Detroit, Michigan, on March 3, 2016. Reuters/Jim Young.
“I’ll admit, he’s taller than me, he’s like 6-2. Which is why I don’t understand why his hands are the size of someone who’s 5-2,” Rubio said to a cheering crowd. “Have you seen his hands?” And Rubio didn’t let up. “And you know what they say about men with small hands,” then pausing for dramatic effect. “You can’t trust ’em. You can’t trust ’em.”
That sent Trump into a tirade about his “great hands” both then, and also a few days later at the Republican Presidential debate in Detroit, noting Rubio’s remark, and holding up his hands for the audience as he spoke: “Look at those hands. Are those small hands?… And, he [Rubio] referred to my hands if they’re small, something else is small. I guarantee you there is no problem. I guarantee it.”
With that, the “small hands” kerfuffle took on a life of its own for a time, as several media outlets picked up on the story, including ABC News, Mother Jones, and others.
The Washington Post later reported that Trump again defended the size of his hands in an interview with the paper’s editorial board. “My hands are normal hands,” he said, according to the Post. “I was on line shaking hands with supporters and one of the supporters said, ‘Mr. Trump, you have strong hands, you have good size hands.’ And then another one would say, ‘Oh, you have great hands, Mr. Trump.’ I had no idea.”
By the end of March 2016, The New Yorker weighed in with a cover illustration titled the “The Big Short” by artist Barry Blitt, in which the illustrator is offering “a reading” of Donald Trump’s palm and hand — by Donald Trump — with various notations made by Trump on the fingers and lines of the palm.

New Yorkers artist Barry Blitt's offering of a palm and hand reading for the cover of The New Yorker magazine, March 28, 2016.
In a short accompanying piece at The New Yorker, Blitt briefly reviewed the practice of palmistry concluding: “it never really established itself as anything more than a pseudo-science.” It was banned by the Catholic Church in the Middle Ages, he further explained, but enjoyed a popular resurgence in the late nineteenth century. In palm reading, he explained, not only are the lines of the palm considered, but also the relative sizes of the hand and fingers. “Speaking of which,” he added, “I hope Donald Trump doesn’t actually become President.” Blitt would also draw Trump on other New Yorker covers with some attention to his hands, including “Grand Allusion “(May 23, 2016), and “Remote Control” (September 2025).
Another New Yorker cover, this one by artist John Cuneo – “A Man of Conviction,” June 10, 2024, following Trump’s hush-money trial where he was convicted of 34 felonies – featured Trump extending tiny hands to be handcuffed.So, what began at Spy with 1988’s “the short-fingered vulgarian” phrase, ended up having quite a run beyond Spy magazine. Yet for Graydon Carter, the Spy editor and prime mover of the “short-fingered vulgarian” phrase, Trump would be unforgiving. As Carter told NPR’s Morning Edition in March 2016:
…He [Trump] blames me for this more than Kurt [Andersen, the other Spy editor]. He’ll send me pictures, tear sheets from magazines… With a gold sharpie, he’ll circle his fingers and in his handwriting say, “see, not so short.” And this [last] April when he sent me one, I should have held onto the thing. But I sent it right back by messenger with a note stapled at the top saying, “actually, quite short.” And I know it just gives him absolute fits. And now that it’s become sort of part of the whole [2016] campaign rhetoric, I’m sure he wants to just kill me …with those little hands…
More Spy Spoofs
Back at Spy, meanwhile, the 1988 edition with Trump on the cover and the fake book review, wasn’t the only time Trump was featured or singled out in the magazine. In fact, over its run, Spy devoted a fair share of copy to “The Donald,” a principal subject of at least eight major articles or features during the magazine’s 1986–1998 run, and numerous other shorter hits. One report noted that Spy averaged one mention of Trump every 25 pages or so. Bruce Feirstein, writing for Vanity Fair in 2015, noted that Spy editors, Graydon Carter and Kurt Andersen, “recognized Trump for what he was… a bombastic, self-aggrandizing, un–self-aware bully, with a curious relationship to the truth about his supposed wealth and business acumen.” And accordingly their stories on him highlighted those traits while probing his deal-maker claims.
Another commentary on Spy and Trump at TheBoweryBoysHistory.com in August 2015 noted:
“…Naturally, Spy magazine and Donald Trump were on a collision course. He was the very thing Spy was designed to mock. Trump was one of the most frequent targets for almost six straight years — in almost every issue. His wobbly finances and bristling reputation were common targets, but the editors were not above more superficial accusations about his marriage or his level of taste.”

Cover of Spy magazine’s inaugural issue, October 1986 with feature story, “Jerks: The Ten Most Embarrassing New Yorkers” – which included Donald Trump. Click for Spy magazine page at Amazon.
In that piece Trump was criticized for his 1980 destruction of the Art Deco Bonwit Teller department store building to make way for the Trump Tower – and specifically, for destroying two Ely Jacques Kahn art moderne frieze sculptures on the front of the Bonwit Teller building. Trump, in fact, had originally promised to preserve the sculptures for the Metropolitan Museum of Art.
Spy had opined earlier in the piece on Trump’s tastes: “Forget the way he has imposed upon all of us his idea of “class” – more a Dynasty [i.e., popular Texas TV soap opera) notion of panache than anything even faintly evoking the uptown swagger that New York epitomizes. Forget the sheer cheesiness of Trump Tower, Trump Plaza, and his casinos… In fact, forget just about everything concerning Donald Trump except the stupid things he says…”
As for the Bonwit Teller sculptures, Trump later saw them as delaying construction on his Trump Tower. “They weren’t even sculpture,” he said. “They were stones with some engraving on them, They were nothing, Just junk.” So he bought in a gang of workers who demolished the sculptures. Trump suffered a bit of scorn in the New York press for his tasteless handiwork, which he attempted to justify/explain away via his invented Trump Organization spokesman, the fictitious “John Barron.” (more on this at film clip below).
Since the Bonwit-Teller depredations, however, Trump’s “out-with-the-old-and -in-with-the-gold” and other Trumpian décor dictums of poor taste have been on full display elsewhere. Not least of these in 2025 is the White House, with its endless gold trim, a demolished East Wing, and a “Mar-a-Lagoed” Rose Garden. Other Trumpian monstrosities are yet to come with a promised White House ballroom and The Arch of Trump. Spy, it turns out, and much of New York media, warned us early on about these vulgarian tendencies. Here’s a PBS/Frontline clip on the Trump-demolished Bonwit Teller sculptures and controversy stirred.
Spy wouldn’t let up on Trump, as it came at him from all directions. There was a tongue-in-cheek profile of the Trump Tower book store featuring various Trump books, Trump Tower postcards, and other Trump souvenirs – “Book Nook: Trumporama on Fifth” by Susan Orelan (September 1987). As Trump’s name was first bandied about as a presidential candidate, Spy included him, then a non-candidate, in their February 1988 review of presidential contestants. Citing some very low polling number for Trump, Spy wryly offered its short column on him, “Nation To Trump: We Need You,” along with a wild cartoon caricature.
Then in May 1989, there came a long cover story on Ivana Trump, Donald’s first wife and business partner during the go-go 1980s. The cover tagline for that story — with a close-up of Ivana’s face — screamed: “IVANARAMA! — An Investigative Tribute To the Most Superficial Trump of All.” Inside, at the story site, the text began with: “She Was a Top Canadian Model and a Top Olympic Skier – Just Ask Her Husband: And She’s a Top Wife! A Top Socialite! A Top Decorator! A Top Fashion Plate! And Now a Top Hotel Executive! She’s Super Glamourous! She’s Supergor-geous! She’s All Over the Place! That Why the Lady Is A Trump!”That story, by Jonathan Van Meter, ran for ten pages. There was also a short two-page story on Donald that followed in that same issue: “Dear Donald: An Epistolary History of A Year In The Life of Donald J. Trump,” covering some 1988-1989 exchanges between Trump, his lawyers and Spy‘s editors.
In a later edition, following Trump’s separation from Ivana, Spy ventured forth with a contest-like appeal to find Trump a new wife, complete with mail-in application form. “Calling all singles and swingles…,” the appeal began, “Spy is seeking heartfelt essays of 100 words or less on the topic, ‘Why I Should Be The New Mrs. Donald Trump’.” Spy explained that three winners would be chosen, each receiving various Spy swag and rare, unsigned copies of The Art of the Deal, while their applications would be forwarded to the Donald.
In September 1989, Spy had cyclist Sydney Schuster file a report accompanied by a detailed map on the “Tour De Trump,” a Trump cycling race promotion staged as answer to the famous Tour de France cycling classic. The Spy story – “Run Amok! Mapping The Tour De Trump’s Mishaps, Foul-Ups and Egregious Exaggerations” – covered the Trump cycling event run between May 5th and May 14th, 1989, reported as it ran in stages between Albany, NY through Pennsylvania, Virginia, Maryland, and ending at Trump’s then under-construction Taj Mahal casino in Atlantic City, NJ. Spy described the Tour De Trump as “an over-hyped, underscrutinized event, characterized by snafus, Wilie E. Coyote shenanigans, critical errors and a remarkably casual approach to facts.”

Photo of the 1989 "Tour De Trump" from a Virginia location.
There was also another Trump-sponsored sporting event designed to help draw attention to Trump casinos in New Jersey – the World Motor Boat Championships, which Spy also covered in its February 1990 edition with a story by John Shaft, “Crimson Tide: Donald Trump Hosts His Own Very Special Disaster at Sea.” In that story, Trump was criticized for moving the race from the more placid waters of Key West, FL to the rougher seas off Atlantic City, NJ in hurricane season, in part to be fan-proximal to his Trump Castle casino. In the race, one death, three broken backs, and other injuries resulted. Said one contestant at race’s end: “Thank God they’ll never have the world championship here again.”. Trump meanwhile, was musing about bringing another even bigger named race, The America’s Cup, to the Atlantic Ocean waters near his casinos.
Spy also had some fun naming Trump “America’s Cheapest Zillionaire” in July 1990 after he was the only person to cash a 13-cent check sent by the magazine as a prank. And a February 1991 Spy piece, titled, “Okay, Now, What’s The Sign For Debt? Our Special Donald Trump Sign Language Translation Guide,” with diagram and series of Donald Trump photos shown making various hand gestures along with short explanatory captions – e.g., “To an IRS agent: My airplanes are worthless”; “To a sexy woman: I want to grab (you) and milk (you),” and others.
Trump in the 1990s

The August 1990 edition of Spy took a stab at predicting Donald Trump’s future fortunes, and cast them as failing.
What does the future hold in store for a former billionaire? Bankruptcy? Substan-tial Weight Gain? An ex-wife in the Czech parliament? A line of grooming products perhaps? Jamie Malanowski assembles a prophetic scrapbook biography of Donald Trump, an eighties kind of guy lost in a nineties kind of world.”
Inside the magazine, the fictional predictive piece looking ahead to Donald’s business doom, was titled: “A Casino Too Far: Pages From the Donald J. Trump Scrapbook, 1990-1995.” That story was prefaced with the following set up:
…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 “king of cash”; and he became the subject of speculations about his ability to service the $3.2 billion debt that is the basis of his empire. Now the saga continues: (followed by eight pages of fake news stories, headlines, society-page gossip and photos).
The fictional piece of predicted bad news for The Donald in the 1990s foresaw total financial ruin, a permanent exit from the public eye, and the loss of iconic assets like The Trump Tower, portraying him as irrelevant and reduced to a figure of tabloid embarrassment
Well, that conjured vision, no matter how justified given Trump’s actual historical performance and practices, did not come true, of course – at least not then or even a decade later. Spy ate crow on that one. Still, there is time yet for a vindication to come. In their hearts, the Spy editors suspected history would prove them right.
Beyond The Laughs
Other of the less-speculative Spy stories, however – those that focused more on actual Trump business information – scored closer to the truth. These Spy stories probed more deeply into the Trump game and came up with important revelations about his business practices and misdeeds, shell games, half truths, and misrepresentations. For example, “The Art of the Art of the Deal: Donald Trump, Author, vs. Donald Trump, Aggrieved Taxpayer,” a detailed November 1989 Spy piece by Frank Cerabino, a reporter with The Palm Beach Post, probed Trump’s purchase of his Mara-a-Logo property. He found — and the Spy story documented — that Trump’s claims surrounding that purchase as described in Trump’s 1987 book, The Art of the Deal, were “simply exaggerated if not false.”
Another Trump story at Spy, this one in April 1991 by John Connolly, probed Trump’s shady business and financial manipulations, was short titled, “How to Fool All of the People, All of the Time.” At the story proper, however, as shown below, it carried a more descriptive and longer title: “How Donald Trump Fooled The Media, Used the Media to Fool the Banks, Used the Banks to Fool the Bondholders and used the Bondholders to Pay for the Yachts and Mansions and Mistresses.”

Opening page of John Connolly’s detailed April 1991 story on Donald Trump “wheeling and dealing” in Spy magazine– which in the magazine, was originally displayed in a sideways/vertical layout.
This detailed story portrayed Trump not as the billionaire he claimed to be, but rather a financially strapped, deceptive operator who manipulated financial records and milked failing companies to support and maintain a lavish lifestyle. Connolly’s story was later published as an Amazon “singles classic” in the Kindle format running 26 pages.
In the end, Donald Trump managed a Houdini-esque escape from his various financial and other difficulties in New York. He also survived and outlived the Spy magazine treatment, but not its legacy. Yet the final outcome and judgements for Donald Trump are still to be determined.

“You Can't Spell America Without ME,” is a satirical “fake memoir” by Alec Baldwin & Kurt Andersen (former Spy co-editor) from 2017, that humorously recounts Trump's first year as president. Click for audio & other book editions at Amazon.
…But the one target [Spy magazine] nailed, probably more often, more incisively, and more presciently, than any other was Donald Trump. The Donald, and in one case, his then-wife Ivana, was the subject of at least eight features in the magazine over the years, along with countless other casual mentions, digs, pot-shots, and sneering asides. The editors peered through the very thin crust of respectability that Trump had cultivated for himself, as a man of great wealth, refined taste, and laser-business acumen, and saw underneath a lying, fraudulent, and extremely vulgar, buffoon. In this, he was the avatar of New York City itself, in all its late ‘80s greed-is-good excess.
…Along the way they dug into his finances, mocked his business failures, trolled him with 13 cent checks (which he cashed), and generally made it clear that while he might have fooled some people, he hadn’t fooled the editors of Spy magazine.
See also at this website, additional history about Donald Trump, including: “Trump on Film: A Partial Listing, 1990-2024,” covering some 30 Trump films. More magazine treatments of Trump at this website include:, “The Trump Dump: New York Magazine, 2016,” profiling a special issue of that magazine and others that chronicle Trump’s early career in New York and beyond. Other stories mentioning Trump include: “Political Science: Randy Newman Music,” regarding nuclear weapons; “I Won’t Back Down” about the use of Tom Petty song in political campaigns; and “Shields, Brooks, Trump,” regarding reaction to some earlier Trump remarks in 2017.
For additional stories on Publishing and/or Politics, see those respective category links. There is also a separate “Topics page” on Magazine History.
Thanks for visiting – and if you like what you find here, please make a donation to help support the research, writing, and continued publication of this website. Thank you. – Jack Doyle.
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Please Support Thank You |
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Date Posted: February 7, 2026
Last Update: February 7, 2026
Comments to: jackdoyle47@gmail.com
Article Citation:
Jack Doyle, “Trump Send-Ups: Spy Magazine,
1980s-1990s,” PopHistoryDig.com, February 7, 2026.
Twitter: https://twitter.com/PopHistoryDig
BlueSky: jackdoyle.bsky.social
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Related Trump Books & Film at Amazon.com…
Sources, Links & Additional Information
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“Presidential Prospects for 1988 – Nation to Trump: We Need You.” Spy, January-February 1988.
Bruce Handy, “Egos A-Go-Go; Trump vs. Julian Schnabel: Dueling Books, Dueling Egos, Spy, April 1988, pp. 44-45 [includes fake book ad for The Art of the Deal].
Jonathan Van Meter, Cover Story, “That’s Why the Lady Is a Trump. A Special Spy Investigative Tribute to Ivana,” Spy, May 1989.
“Dear Donald: An Epistolary History of A Year In The Life of Donald J. Trump,” Spy, May 1989, pp. 98, 100.
Sydney Schuster, “Run Amok! Mapping The Tour De Trump’s Mishaps, Foul-Ups and Egregious Exaggerations,” Spy, September 1989, pp. 100-102.
“The Art of The Deal,” Wikipedia.org.
Frank Cerabino. “The Art of the Art of the Deal” (fact-checking Trump’s financial claims in The Art of the Deal”), Spy, November 1989.
John Shaft, “Crimson Tide: Donald Trump Hosts His Own Very Special Disaster at Sea” [Trump Castle World Motor Boat Champ-ionship], Spy, February 1990, p. 88.
John Brodie. “The Spy Trip Tip: Where Playing to Win Was Born — Log Cabin Queens, Visiting Trump’s Boyhood Home,” Spy, March 1990.
Julius Lowenthal, “Every Man Has His Price. In Some Cases, 13 Cents” [also with cover billing as:: “An Exclusive Spy Prank: Who is America’s Cheapest Zilioniare?”], Spy, July 1990.
Jamie Malanowski, “A Casino Too Far, A Speculative, Alternative History of Trump’s 1990s,” Spy, August 1990.
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John Connolly, “How to Fool All of the People, All of the Time: How Donald Trump Fooled the Media, Used the Media to Fool the Banks, Used the Banks to Fool the Bondholders, and Used the Bondholders to Pay for the Yachts and Mansions and Mistresses,” Spy, April 1991.
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Books at Amazon.com…







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