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The New Yorker writer who profiled Donald Trump in the 90s delves into the Republican’s mentality, and explains to the Guardian’s Alex Needham why he thinks he’s destined to drop out.

Mark Singer. Photograph: Richard Saker/The Observer

Born in 1950, Mark Singer has been a writer for the New Yorker since 1974 (“There was no reason to leave,” he tells me as we sit outside a café near his home on Manhattan’s Upper East Side). In 1996, his then editor Tina Brown commissioned him to write a profile of Trump with the words “He’s totally full of shit, you’ll love him!” After months getting a full immersion into Trump’s world, one highlight being a ludicrous meeting between Trump and Aleksandr Lebed, in which Trump proudly showed the Russian general and Kremlin fixer a shoe he’d been given by Shaquille O’Neal – Singer wrote a 10,000-word profile that nailed the narcissism, superficiality and cynicism with which the world is now so alarmingly familiar. It concluded that Trump had “aspired to and achieved the ultimate luxury, an existence unmolested by the rumbling of a soul”.

Naturally, Trump didn’t appreciate Singer’s efforts, attacking him in his book Trump: the Art of the Comeback, in a letter to the New York Times (“he was not born with great writing ability”), and finally in an irate missive that read: “Mark, you are a total loser! And your book (and writings) sucks!”

These last two sentences are proudly printed on the back of Singer’s new book Trump and Me, which revisits his profile in the light of Trump’s presidential campaign. Given Singer’s probing wit and Trump’s essential ridiculousness, it is very funny, though the implications of a Trump presidency seem increasingly less amusing in the light of the hatred he has unleashed. “I am afraid. Everybody I know is afraid,” Singer says. “If Hillary Clinton wins, listening to the sigh of relief just on this island, we might have a carbon dioxide overload crisis. You’ll see these trees shooting up.”

Singer says that Trump is “the most unapologetic … there has to be a word stronger than hypocrite, there really does.” He is despairing that some voters – stoked by the email scandal and the WikiLeaks revelations about her attempts to undermine Bernie Sanders – think Hillary Clinton is more dishonest than Trump. This, he says, “is what really makes you want to blow your brains out. It makes you want to go back and find patient zero and think, when was the moment where we stopped being willing to fund public education in this country, that it became so egregious that we no longer could have people who understood the constitution, the checks and balances? Trump says: ‘I love the ill-educated.’ You bet he does.”