49 Tremendously Vulgarious Ways “Spy Magazine” Described Casino Operator Donald Trump, 1986-1994

From 1986 to around 1994, Spy Magazine skewered the New York City media and political scene and often exhibited a special focus on real estate developer Donald Trump. See — before Trump convinced millions of people he could be president, Trump regularly convinced people with millions of dollars that they should give their money to him. This was, generally speaking, bad advice. Spy Magazine’s investment in regularly exposing Donald Trumps’ ridiculousness inspired Esquire to launch a SPY Magazine pop-up on its website during the election, with posts from Spy co-founder Kurt Anderson and former Spy contributors like Nell Scovell and Bruce Handy. If you’ve never heard of Spy, than knowing that Spy definitely inspired Gawker might give you a reasonable idea of what it was. (I also recommend Spy: The Funny Years, which is practically free because nobody but me cares, apparently.)

The entire Spy Magazine archives are available on Google Books, though, and a nice breeze-through of Trump-related search results isn’t an entirely insufferable experience. (Spy Magazine was definitely one of Gawker’s formative texts, and we see how that turned out.) A lot of old Spy articles are, well, prescient. Like this one, which takes the mainstream press to task for not aggressively fact-checking his proclamations of wealth/worth and thus dooming the investments of so many media consumers. Or, you know, this one:

But Spy Magazine really excelled at Trump-related insults. This listling contains just some of many, ripped mercilessly out of context for your enjoyment.

Spy Magazine Describes Donald Trump, 1984-1994

1. “Shuttle-owning dilettante-megalomaniac”

2. “Doomed millionaire”

3. “Synthetically good-looking deadbeat”

4. “School-yard bully giving way to patronizing wiseass”

5.  “The short-fingered one”

6. “Deal-maker extraordinaire”

7. “Trump, it seems, knows how to make another sound. It goes: NYEH-NYEH-NYEH-NYEH NYEH.”

8. “A cheeseball”

9. “…Trump may have been the punchline of most of the jokes told by the swarm of aging, bad comedians at the party (“Marla, you picked a loser!” said Pat Cooper), but his short fingers were as limber and active as ever.”

10. “A short-fingered casino operator”

11. “Floundering casino operator”

12. “Sinking casino operator”

13. “Casino-operarting hustler”

14. “Hustler-on-his-best-behavior”

15.  “The garlic. The crucifix. The stake through the heart. The holy water sprinkled on the soil from his native Queens that he must sleep in every night — evidently none of them have finished off Donald Trump.”

16. “A supercanny, supersharp top investor”

17. “A superbusinesslike, superresponsbile top investor”

18. “The world’s top judge of architecture”

19. “Would-be Upper West Side ravager”

20. “Long-running scamp”

21. “A fool and a liar and a deadbeat”

22. “Short-fingered indentured servant”

23. “…not just some cartoon character, a guy with a comb-over and a press agent and a board game named after him; he is and always has been a real and fairly treacherous human being.”

24. “Marginally solvent financier”

25. “Short-fingered vulgarian”

26. “Creative, hands-on, person-to-person superguy”

27. “Debtor-adulterer”

28. “…Goldberger had bigger things on his mind, namely Trump’s unrelentingly meretricious taste in architecture, Trump’s ethics, Trump’s self-aggradizing propaganda and the future of New York City.”

29.  “The very symbol of greed, vulgarity and bluster”

30.  “High-class, swanky real estate mogul”

31. “A man of obviously limited abilities”

32. “The biggest, richest, shortest-fingered catch in town!”

33. “Scalp-tightened self-promoter”

34. “A vanity author”

35. “Short-fingered acolyte”

36. “Nobleman-lounge singer”

37.  “Flyaway-haired mogul and author”

38. “Forget the way he has imposed upon all of us his idea of “class” — more a Dynasty notion of panache than anything even faintly evoking the uptown swagger that New York epitomizes. Forget his noxious tactics with tenants he wishes to evict. Forget the sheer cheesiness of Trump Tower, Trump Plaza and his casinos; forget the way he seems to have the Times in his back pocket; forget the hustler-on-his-best-behavior manner. In fact, forget just about everything concerning Donald Trump except the stupid things he says.”

39. “The epitome of Roaring Eighties-style excess”

40. “Our very own Queens-born megamillionaire”

41. “An eighties kind of guy lost in a nineties kind of world”

42.  “Highly leveraged vice king”

43.  “Vulgarian builder”

44. “When a member of Oprah Winfrey’s TV audience had the temerity to ask them about 20/20’s report that Donald only spends four to six hours a week with his children, he responded, “I would say that I spend enough time with the children. I think they’re pretty well covered.” Hear that, naysayers? They’ve got the kids covered. No problem. And we’ll bet those four, five or six are super-quality hours. With top kids.”

45. “Capitalist Genius and Creator of Wealth”

46. “Supersavvy top financier”

47. “Low-profile noncandidate”

48. “Would-be president”

49. “When another guest ribbed Trump about his threatened presidential aspirations, the Queens-born casino operator replied, “Look, would you run for office if you paid almost no taxes last year? Like, duh… we’re sure he was just kidding.”

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Riese is the 41-year-old Co-Founder of Autostraddle.com as well as an award-winning writer, video-maker, LGBTQ+ Marketing consultant and aspiring cyber-performance artist who grew up in Michigan, lost her mind in New York and now lives in Los Angeles. Her work has appeared in nine books, magazines including Marie Claire and Curve, and all over the web including Nylon, Queerty, Nerve, Bitch, Emily Books and Jezebel. She had a very popular personal blog once upon a time, and then she recapped The L Word, and then she had the idea to make this place, and now here we all are! In 2016, she was nominated for a GLAAD Award for Outstanding Digital Journalism. She's Jewish and has a cute dog named Carol. Follow her on twitter and instagram.

Riese has written 3200 articles for us.


  1. Maybe they meant to say he spend 4-6 hours a week with Tiffany, because the way he talks about the others, Ivanka specially is creepy or at the very least bordering it.

    • They’re actually the ones who invented that meme; it was popularised by John Oliver, who noted Trump was so upset about it that he still sends pictures of his fingers to the person who wrote that column in an attempt to prove that he doesn’t have tiny fingers.

  2. I wish they’d announced his victory like this. “BREAKING NEWS: high-class, swanky real estate mogul wins presidency”.

  3. Maybe pay credit where it’s due? For all the shit journalists have been getting (from both sides) for simply doing their jobs, I’d think Graydon Carter would leap to mind?

    Most of those Spy bar a were from him. In fact, he has continued to deride the short-fingered vulgarian since joining Vanity Fair in 1992.

    He’s been keeping it up the past few months. You know, considering his long career in satirical journalism in the vein of UK’s Private Eye (not Gawker trash), I’d think someone who works in the industry would recognise Carter’s pawprints on this. The least you could do is credit journalists for their work.


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