The Inside Story of Caitlyn Jenner’s Historic Vanity Fair Cover

Last month, Caitlyn Jenner introduced herself to the world in a groundbreaking,22-page Vanity Fair feature photographed by Annie Leibovitz and written by Pulitzer Prize winner Buzz Bissinger. Now, in this new documentary by Jeremy Elkin for VF.com, Jenner, Vanity Fair editor Graydon Carter, and the magazine’s staff reflect on putting the story together, keeping it under wraps in the hacking-scandal era, and unleashing it to a response that was even more overwhelming than expected.

Previously known to the world as the Olympic gold-medalist and Kardashian patriarch Bruce Jenner, the magazine’s cover subject had spent months hiding out in her Malibu bunker. She caught her first reflection of “Caitlyn”—in full hair, makeup, and clothing—in a mirror positioned behind her during the photo shoot. “From a distance, I looked in the mirror and thought, Oh my God,” she said. “It’s the first time I really saw an image of me, who I am.” Jenner says the image assured her: “This is going to work. . . . We’re going to be O.K.”

Given the enthusiastic response to Caitlyn’s debut, the feature proved to be more than a landmark milestone for Jenner and the transgender movement—it was also a proud moment for print media. Says Carter, “It’s a way that a magazine cover [still works] and you can use the Internet rather than fight the Internet on a big story.” The magazine did, however, have to take special security precautions to protect its exclusive.

“The photos and text were put onto one computer that was off-line,” explains associate managing editor Ellen Kiell. “Each day, the designer, copy editor, researcher would work on that one computer.” When it came time to deliver the feature to the printer, Kiell flew to Lexington, Kentucky, to personally hand-deliver the finished product. Carter adds that the photo shoot and printer were safeguarded by the same security team that patrols the V.F.Oscar party.

The secrecy worked, and the feature gracefully launched Caitlyn as the elegant, inspiring, authentic person she had spent decades struggling to become.

Marveling how her coming-out story eclipses all of Bruce’s achievements—Olympic gold medal included—Jenner says tearfully, “I never thought that someday I would be able to do this.

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