Ms. Morrison, now at The New Yorker, remembers Mr. Hainey, just off the boat from Chicago, as a kind of Jimmy Stewart character. “Before he had the new-wave hair and important eyeglasses and Thom Browne suits, he was this kid with hay in his hair,” she said. “That made him the perfect candidate to do certain kinds of interactive Spy stories. Stories that in another context would probably be called hazing.”
On one such assignment, Mr. Hainey was tasked with chasing after girls on Amsterdam Avenue to test-drive a variety of actual celebrity pickup lines. “He was terrified,” Ms. Morrison remembered. “I think he actually did pretty well with [Warren] Beatty’s line, which was ‘Make a pass at me.’”
Anthony Haden-Guest’s pickup line, on the other hand—“God meant for us to be naked together”—did not go over so well.
“He had, from the beginning, in his understated Midwestern way, a combination of confidence and gameness,” said Kurt Andersen, the Spy co-founder-turned-novelist, “just a kind of willingness to do whatever we asked.”
As deputy editor of GQ, Mr. Hainey has interviewed some of the most iconic cultural figures of our time, from Keith Richards to Clint Eastwood to Bruce Willis, the cover boy of the magazine’s current issue. In his book, though, Mr. Hainey talks about how he still needs to get into character before doing reporting. “By nature I’m a shy person. I get rattled easily,” he said.
Perhaps, but there is something of a rascal under his soft-spoken Midwestern exterior as well. When The Observer first met Mr. Hainey, for example, we had been instructed by the writer Donald Antrim to give him the middle finger, because that was how Mr. Hainey caught Mr. Antrim’s eye at a party two decades back.
During those early days in the city, Mr. Hainey lived in a Quaker-run boarding house on 15th Street, where, in exchange for a bed, a desk, two meals a day and a communal bathroom, he paid a token rent and did chores, like washing dishes and shoveling the sidewalks. “It always seemed to be snowing,” he recalled.
Now Mr. Hainey is a perennial front-rower at fashion weeks the world over, and along with his wife, Brooke Cundiff, an executive at Gilt Groupe, he represents one-half of a New York fashion power couple. Mr. Carter describes him as a loyal regular of his exclusive West Village watering holes, the inns Waverly and Beatrice, so “I see a lot of him through the bottom of a highball glass.” But none of that mattered when Mr. Hainey found himself trolling through Chicago hospitals and morgues, chasing after the ghost of his father. Or when he found himself face-to-face with the men who had worked alongside his dad back in the day, grizzled newspapermen who still played by an old-school code of silence, admitting nothing but betraying everything.
“Guys stick together,” they said.
“I don’t think you have the right to know the truth,” they said.