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In his new memoir, “When The Going Was Good: The Adventures of the Magazine’s Last Golden Age,” former Vanity Fair editor Graydon Carter talks about the glorious days of magazine publishing and the stewardship of two A-Half trendset titles.
Among the colorful highlights Carter writes from his career in the venerable Condé Nast estate, there are the sinking needed to protect Caitlyn Jenner’s 2015 transition at Vanity Fair.
Read the excerpt below and don’t miss Jane Pauley’s interview with Greydon Carter “CBS Sunday Morning” March 23rd!
“When It’s Good” by Greydon Carter
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We’ve always been hoping off the newsstand and keeping an eye on covers that will send out word-of-mouth online over the next few years. Sometimes the quest defeated us unexpected means. If deep throat masking was the biggest journalistic scoop of my time at Vanity Fair, then the biggest scoop on the overall culture was our cover on Caitling Jenner. Jenner remembered as the Olympic demon, who appeared in Wheatie’s Box as Bruce Jenner. Jenner was tall and still looked good, and it had a bit of help from colorists and surgeons. He had a minor and de-seasoning film career early on, and by the time of transition, Jenner was the stepfather ordered by the hybrid Kardashian on a reality TV show. Jenner has become a bit tragic. However, the word that there will be dramatic news has begun to permeate.
One day I called Jane Salkin to my office and said, “How about Bruce Jenner?” There was a story that came to mind about Jenner performing reassignment surgery. “At one point, Jenner announces. Why at the Vanity Fair? Our first approach was flat. Then Jenner switched to a publicist who Jane was a friend of. After a lot of towing and Frowing, Jane had some news. Jenner was a game to play it with us, she said.
I’ve now got into deep world mode to get covers, photos of the inside and stories. As we did with our deep throats, we set up a special room in our office and covered the windows with kraft paper. There’s nothing to doubt about that! There was one key in the room and a computer that handled traffic on a separate server from the one that handled the rest of the magazine. Only eight people in the office knew about the project. I assigned Annie Leibovitz to take a photo, and assigned Pulitzer Award-winning journalist and author of Friday Night Wright, Buzz Bissinger, to do the story. I thought Buzz was ideal. He could talk about sports and considering he dabbled in a bit of cross dressing, he could also speak in the delicate language of a woman. When Bruce began the transition process, Buzz made many trips west. The plan was for Bruce to undergo surgery and recover in isolation at his Malibu home. Our agreement was that no one else was allowed to visit him during this period. Just buzz. As the report progressed, there were fascinating issues, such as finding clothes for a 6-foot, 2-inch former athlete woman, and smuggling the world’s most famous photographer into a house surrounded by paparazzi. Words about Jenner came out, and there was even a news helicopter heading overhead. Place the security guard around the perimeter. And we put the entire crew in two big vans with darkened windows for the filming. Jane and Buzz were one of them, such as Buzz’s editor Dana Brown. Jane then explains to walk along with Annie’s team. “The house had a beautiful view of Malibu. A very modest house. But it’s a beautiful pool. You go up the stairs and when I come out, this person is heading towards me in a silk robe with the feathers of a Malabu.
Once you have the story and filmed, it’s time to pick a cover and figure out what to say about it. We messed around with any number of options. Finally, I wrote the line “Call Me Caitlyn.” I thought her name would be everywhere by the time the issue hit the newsstand. There’s no need to say anything more. We were still relatively primitive digital time, but we decided to make it the first cover we’ve ever released online. There’s no need to wait for printing, binding or delivery trucks. All sources of leaks. I created a brief explanation and a short video that was taken during filming. At noon on the day we were appointed, we released the story to the world. Dozens of us were sitting at a long borrowed meeting table watching the traffic on a large TV monitor. It started slowly, and after a few minutes clicked, it began to climb until the graph arm was completely vertical. I’m not sure if we can “break” the internet, but we certainly got closer if possible.
From Glendon Carter’s “The Going Good: The Editor’s Adventures,” published on March 25, 2025, by Gredon Carter, by Penguin Press, the stamp of Penguin Publishing Group, division of Penguin Random House. Copyright©2025 by Graydon Carter.
Mladen Antonov/AFP via Getty Images
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