Jeffrey, Who? A Plane Ride with Donald Trump

"Since I began writing Profiles for The New Yorker, fifty years ago, my preferred subjects have been non-celebrities, people who for whatever reason interested me and, ideally, had been written about rarely, if ever. Reporting a condensed biography of a living person tends to be quite intrusive, involving many hours of one-on-one interviewing and fly-on-the-wall observation. That a subject and I were not friends didn't mean that our interactions should feel stilted or adversarial."

"Occasionally, I felt the need to protect a subject from himself. In the mid-eighties, I wrote about an art dealer who by his early thirties had become internationally well-known as a relentlessly competitive trader in antique atlases and maps, rare books, engraved prints, and eventually much more. He once invited me to accompany him to a meeting with a highly valued client provided that I pose as his employee."

Fifty years of Profiles focused on non-celebrities rarely covered elsewhere. Condensed biographies proved intrusive and required many hours of one-on-one interviewing and fly-on-the-wall observation. Protective intervention sometimes occurred to shield subjects from their own behavior, as when an art dealer invited a reporter to pose as an employee and later admitted the portrayal's accuracy. One Profile was accepted despite an expectation of unflattering results: the 1996 piece on Donald Trump, undertaken without leverage to refuse. A plane ride with Trump and Ghislaine Maxwell, during which Maxwell called a friend named Jeffrey, became an enduring memory.

Read at The New Yorker