Spy vs Everyone (but especially Donald Trump)

The most influential magazine of this century stopped publishing in 1998, but its legacy is both invisible and everywhere, from Twitter to the American presidency

I AM PRETTY SURE that the first time I came across Spy magazine was in September, 1991. Most probably I was introduced to it by the editorial team of The Red Herring, a satirical magazine published by SSMU, the Students Society of McGill University. The Herring (motto: “McGill’s only intentionally humorous publication") had been launched a few years before, and I had signed up during frosh week to see if I could be some sort of contributor. 

At that first meeting, I recall one of the editors mentioning how Spy was the greatest magazine on Earth, and how in both tone and content, it was exactly the sort of thing they would be looking for in contributions to the Herring. I don’t think I had heard of Spy, or if I had, I hadn’t given it much thought. But I wanted to write for the Red Herring, so I went out and hunted down a copy. It was easy enough to find on the newsstand – the cover of that month’s issue of Spy had Bruce Willis on the cover, photoshopped naked and pregnant in a parody of a sensational picture by Annie Leibovitz of Willis’s then-wife Demi Moore that had just appeared on the cover of Vanity Fair. 

Of course, by late 1991 Spy was already legendary, in the right circles anyway. The New York based magazine was the mongrel descendent of the National Lampoon, Mad Magazine, and Tom Wolfe, though that was all Boomer crap as far as I was concerned. Spy, on the other hand, was a revelation. When I started reading through that first copy, I was by turns puzzled and amused, with most of the in-jokes and boldface name references going totally over my head. But I fell straight up in love with the writing.  I remember thinking, You can do that?

What Spy brought to the table wasn’t just satire, it was satire of a specific sort: Self-conscious, ironic, and more than a bit smarmy, with a steady flow of juxtapositions of the high-brow and the utterly juvenile. But more than anything, what Spy did was break down the detached and “objective” fourth wall of journalism, inviting the audience into the back rooms of the sausage factory, pointing at everything and everyone, and going – “hey, isn’t all of this kind of shit?”

For ironic, overly-educated but still overly-juvenile undergrads, it was a drug like no other. Over the next few years working on the Herring, we freely stole Spy’s entire schtick – the tone, the jokes, the pranks, everything, unfortunately, except the actual cleverness.

Spy was founded in 1986 by Kurt Andersen and Graydon Carter, two outsiders (Andersen was from Nebraska, Carter from Canada) to the New York media scene. Their key insight was to realise that there was an audience for journalism that spoke to the audience in the voice that journalists used when talking to one another after work,  in the bar, at parties, or just hanging around the newsroom after hours. What this meant, practically, was a license treat the entire culture – politics, business, media, society – as a fodder for what amounted to celebrity commentary. Gossip, if you will. 

Their targets ran the gamut of the era’s listers from A to D: Martha Stewart, George H. W. Bush, Steven Segal, Arnold Schwarzenegger, the Kennedys, the Clintons, Bruce Willis and Demi Moore, Princess Diana, the Wall Street swells and Hollywood power brokers, and everyone in between. If you were any combination of rich, or powerful, or pretentious, or just an asshole, you were in Spy’s sights.

But the one target they 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. 

Spy’s conceit was to always refer to him as “short-fingered vulgarian Donald Trump”, a childish insult that also gave the writers a way of making fun of his penis size without ever coming right out and saying it. Along the way they dug into his finances, mocked his business failures, trolled him with 13 cent cheques (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. 

Trump swallowed that hook, over and over again; to this day, Andersen and Carter both delight in recalling how often Trump would write to complain about the treatment, sending them pictures of himself with his hands circled in black sharpie, with a note saying “see? Not so small!”

Life is long and the half-life of gossip is short. Graydon Carter left Spy in 1991 for the more lucrative, and squarely establishment, job as editor of Vanity Fair.  Kurt Andersen left in summer of ‘93, handing things over to Tony Hendra, a veteran British satirist who was best known (to us, anyway) as the guy who played Spinal Tap’s manager, Ian Faith. The magazine was never the same. It got sold, changed editors a few more times, and hung on until 1998, its energies and influence long spent. 

Spy magazine is a quarter century gone (its entire archive is online here) but its impact on today’s media is almost unquantifiable, and its lasting legacy is in the type of journalism it fostered. The magazine’s direct offspring include The Onion as well as the Dave Eggers empire, but the one true journalistic descendant was Gawker, the online New York-focused content vertical that dominated mid-noughties digital media. Gawker’s “everyone’s a fraud” tone was pure Spy, an influence its founding editor Elizabeth Spiers has openly boasted about.  Gawker is itself now gone too, brought down by Peter Thiel in a revenge lawsuit for the ages – but that’s another story. (As for the Red Herring, it published in fits and starts, went online, and eventually seems to have ceased publication in 2013 or so).

But beyond specific outlets, the infamous Spy style is ubiquitous now, to the point where it is pretty much the default conversational tone of online culture: snarky, gossipy, mercilessly mocking, what Gawker’s Tom Scocca, in a hugely influential essay, called “smarm”.

In 2015, Donald Trump decided to make a run for president of the United States of America.  In a piece for Vanity Fair that summer, with Trump’s candidacy just underway, former Spy contributing editor Bruce Feirstein reminisced about their fun days mocking Trump. He ended by confidently predicting that there was no way he would win: “Short-fingered or not, on so many, many levels, the presidency is beyond his grasp.”  As the campaign came to a close in 2016, Hearst Media even launched an ersatz online version of Spy to lampoon a candidate they were sure would, as they thought he always had done, fall flat on his face.

But time has a way of making fools of us all, including (maybe even especially) those who thought they had taken the measure of their enemies, and found them coming up short. Not only did Trump win in 2016, he will most likely win again in 2024. I haven’t seen any self-congratulatory chortling from the old Spymeisters this time around.

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See you in the comments! — ap