While reporting a cover story for GQ magazine in 1983, Graydon Carter spent some time with a brash 37-year-old Manhattan real estate developer. He shared his impressions of the rising mogul over lunch with Kurt Andersen, a friend and fellow journalist.
“Graydon said, ‘This guy, Donald Trump,’ — whom we’d barely heard of — ‘for a tall guy, he has the shortest fingers I’ve ever seen,’” Andersen recalled.
When Andersen and Carter teamed up not long afterward as the founding editors of Spy magazine, a satirical monthly known for skewering the elite, they used that observation to merciless effect, often describing Trump with the epithet “short-fingered vulgarian.”
To celebrate the 40th anniversary of its founding, Spy, which published from 1986 to 1998, will post one story a day from its archive, with commentary, on Substack. The pop-up version of Spy is scheduled to begin Oct. 5 and will run for about a month. Each vintage article will feature Trump, a fixture of the magazine.
Spy had other favorite targets in the go-go era, including the hotelier Leona Helmsley, former Secretary of State Henry Kissinger and top editors of The New York Times, but Trump was No 1.
“In New York in 1986, there was a big carnival of loud voices,” Carter said. “He was the loudest. He was a perfect signature character: the pomposity, the gold, the burgundy stretch limousine. He was out there and in your face every day, it seemed, much as he is now.”
President Trump did not reply to requests for comment for this article. But he shared his view of the magazine in an interview for the 2006 book “Spy: The Funny Years.” “It was fun even when Spy was knocking the crap out of me,” Trump said. “But it’s more fun now that I’m on top and Spy is gone.”
The magazine’s tone — urbane, mischievous and sometimes venomous — set it apart from the usual journalistic fare. In a 1990 article, The Wall Street Journal described Spy as “cruel,” adding that many subjects of its profiles found them “humiliating” and “traumatic.”
Tom Phillips, the magazine’s publisher and a co-founder along with Carter and Andersen, said that deflating bloated egos was part of the mission. “I always felt like, ‘This is what we’re doing — don’t be squeamish about it,’” Phillips said.
Though steeped in satire, Spy took its reporting seriously, with five fact checkers on staff. Susan Morrison, the magazine’s executive editor, recalled the long hours that went into a 1989 cover story on Ivana Trump, Trump’s first wife, who was born in Czechoslovakia. Some of that work went into checking Trump’s claims about her athletic accomplishments in his 1987 best seller “The Art of the Deal.”
“One thing I remember is getting the coach of the Czech ski team on the phone to confirm that Ivana was never on any Olympic team,” Morrison, now the articles editor at The New Yorker, said.
That article, with the cover line “Ivanarama,” marked a turning point in the Spy-Trump relationship.
“It was the first time we heard from him and his lawyers threatening to sue us,” Andersen said. “That was interesting.”
Morrison recalled that Trump would “rip pages out of the magazine and scrawl on them with gold sharpie and mail them back to us: ‘You’ll hear from my attorney.’”
The ungracious reactions of people in positions of power only emboldened the staff. Spy soon sent checks for tiny amounts to wealthy people as part of its search to find “America’s cheapest zillionaire.” Trump was named the winner after he redeemed a check for 13 cents.
In the latter part of Carter’s 25-year run as the editor of Vanity Fair, Trump frequently targeted him on social media. In 2015, weeks before announcing his candidacy for president, Trump sent Carter a clipping of a magazine ad for “The Art of the Deal.”
“He circled his hands in the ad and wrote, ‘See, not so short,’” Carter recalled. “I wish I had kept it. I sent it back and said, ‘Actually they look quite short to me.’”
If Spy were publishing today, would it be so bold in its treatment of Trump, given that he has repeatedly attacked news organizations and has tried to bar major media outlets from the White House press pool?
“Probably, given what Spy was,” said Andersen, who went on to be the editor of New York magazine and has published several books, including a new novel, “The Breakup.” “Being threatened with lawsuits — he never sued, of course — wasn’t the Justice Department looking to prosecute us, but it was not nothing at the time.”
The Spy team, including the writers Bruce Handy and George Kalogerakis (a former deputy editor in The Times’s Opinion section), fell easily back into its old groove while assembling the Trump-centric articles and commentary for the Substack pop-up.
“Our great hope with this,” Andersen said, “is that he or one of his press people will call us horrible scumbags.”
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