In late 2014, Graydon Carter, then the editor of Vanity Fair, was meeting with features editor Jane Sarkin and had a thought, although the kind of thought one usually keeps to oneself. (Carter is also the founder and a co-editor of AIR MAIL.)
It had been reported over the years in the tabloids that Bruce Jenner, the gold-medal-winning Olympian and late-70s icon, was secretly a cross-dresser. To a new generation, Jenner was the sad-sack husband of Kris Jenner, father to Kendall and Kylie, stepfather to Kim, Kourtney, and Khloé, patriarch and bit player on Keeping Up with the Kardashians.
Jenner had been spotted leaving the Beverly Hills Surgical Center earlier that year with a bandage around his neck after reportedly undergoing a laryngeal shave, a process to minimize the size of a man’s Adam’s apple. It couldn’t be denied that Jenner had begun looking more and more like a woman. Other paparazzi shots of Jenner began popping up with his appearing to have what looked like budding breasts, a sign of estrogen-hormone therapy common among those making a male-to-female transition.
So Graydon said to Jane, “Why don’t we reach out to Bruce Jenner and offer him a cover.” Was Jenner ready to come out, and publicly, on the cover of Vanity Fair?
Jane was mortified. I don’t think this was a call she wanted to make. But she did as she was told; found the only contact for Jenner she could find, his speaking-engagement agent; and left a message.
A few months later, Jane called and asked me to come down to her office. The look on her face told me something was afoot. “Close the door.” I did. “I just got a call from Alan Nierob”—Alan was a longtime publicist, part of the deep state of the celebrity-industrial complex, representing a number of big stars over the years, like Mel Gibson, Denzel Washington, Liam Neeson, and others—“about Bruce Jenner.”
Jane took a deep breath. “Bruce … has begun the transition to becoming a woman,” she whispered.
“What the fuck!? Really?”
“Shhhh. And she wants to debut on the cover of Vanity Fair. You can’t tell anyone. Annie’s going to shoot it. We need a writer—what about Buzz?”
Buzz was Buzz Bissinger, one of my writers. He made perfect sense. Born Harry Gerard Bissinger III in New York, Buzz had a pedigreed biography and top-notch education. His father was a Wall Street big shot, and he’d attended Phillips Academy in Andover, Massachusetts—where his roommate was future Patriots coach Bill Belichick—then the University of Pennsylvania.
He went on to a sparkling career in journalism and wrote about sports as well as anyone. His 1990 book, Friday Night Lights, which has sold more than two million copies, was turned into the 2004 film and the successful NBC television series, which ran from 2006 through 2011. It’s considered one of the best sports books ever written.
When Graydon hired Buzz, in the mid-90s, you would have described him as a typical preppy, in button-down shirts, blazers, and khaki pants or bland suits. But in the 2000s, something started to change with Buzz. He began showing up at the office, book parties, and other magazine events in head-to-toe leather, wearing mesh shirts, steel-tipped high-heeled boots, and eye shadow, with chunky chains around his neck. It wasn’t a slow transformation; it was all of a sudden. Overnight, he’d gone from Gene Siskel to Gene Simmons.
People would talk, whisper, “What’s going on with Buzz?” But Buzz didn’t seem to give a shit. Whatever this was that he was going through, it was his, he owned it, and he seemed happier and more confident. Call it a midlife crisis or identity crisis; whatever it was, he came out the other end exactly who he wanted to be. Harry Gerard Bissinger III was gone. Buzz had been reborn.
Unshackled and unrepentant, freed from judgment and judging, Buzz wasn’t just the best man for the job, he was the only man for the job. It was simple math: Gender Identity + Sports = Buzz. Interviewing Bruce Jenner was tailor-made for him.
I called Buzz and explained what was going on, that he would have exclusive and unfettered access to Jenner as he began his transition to—well, we didn’t know to whom, as Jenner hadn’t picked out a name yet. I told him that he could tell no one what he was up to. Immediately, Buzz was in.
Buzz spent the next three months with Jenner in her Malibu home as he slowly made the difficult transition to she. And her name was Caitlyn. Caitlyn Jenner. As Buzz later wrote in the story on Jenner’s transformation, “This is the most remarkable story I have ever worked on in 38 years as a journalist … witness to the final months of one of the most iconic male athletes before he disappears and a woman appears in his place.”
And it really was a remarkable story. Just as journalists had been embedded with units in Iraq a decade earlier, Buzz was embedded with a celebrity on the verge of doing something that had never been done so publicly before. Jenner was incredibly open with Buzz in a way that many subjects aren’t, trusted Buzz with his, and then her, narrative. They grew close.
From an operational standpoint, this would turn out to be the easy part. Even though Jenner was hounded by the paparazzi in Los Angeles, Buzz could come and go with relative anonymity without its being connected to Jenner’s transformation and to a Vanity Fair project. The photo shoot was another story.
How do you do a secret photo shoot with Annie Leibovitz, arguably the most famous photographer in the world, and Bruce Jenner, whose every move was watched, in a dress and heels, without someone telling someone, or something leaking? Or worse, a paparazzi photograph of the shoot?
The photo shoot—a one-day affair at Jenner’s home on top of a ridge in Malibu overlooking the Pacific—was scheduled for May 6, 2015. On a typical cover shoot there might be upward of 20 or 30 people, even more if it was for a Hollywood Issue and multiple subjects. This was a stripped-down operation. Annie had a much smaller team than usual, just a few assistants. Our fashion and photo teams were four or five people. There was no D.J. playing music, no catering team, just a few sad trays of sandwiches and crudités on Jenner’s kitchen counter.
Security was tight. We had flown in our own security team from New York, headed by Keith Duval, a former N.Y.P.D. cop who looks like a movie star or the best-looking Kennedy you’ve ever seen. He had a number of his men stationed around the perimeter of the house, with walkie-talkies and binoculars, scanning for paparazzi hidden in the brush and scrub of the Santa Monica Mountains, or an incoming drone.
I’d flown out the day before with Jeremy Elkin, Vanity Fair’s one-man video department. Buzz, Jeremy, and I were given instructions to drive to Zuma Beach, in Malibu, at two P.M. and wait in the parking lot for someone from Keith’s team to come get us. We were collected and driven up the winding road to Caitlyn’s modern concrete-slab house, which looked like a World War II bunker.
There was a small tent set up outside, and our cell phones were taken from us. There would be no phones allowed in the house during the shoot.
Jenner is six-foot-two, and in heels she towered over everyone. She looked stunning. It was a jaw-dropping transformation. You have never seen a subject as excited to be part of a photo shoot, her first as a woman, getting made up by a professional makeup artist, having one of the most famous hairstylists in the world, Oribe, do her hair. Caitlyn browsed through the racks and racks of clothing, all in her size, that Jessica Diehl, our fashion director, had pulled for the shoot.
Annie was moving from room to room so the photos had different backgrounds. There was Caitlyn in a gold Badgley Mischka gown staring out at the Pacific in her living room; in Zac Posen in her bedroom; leaning against a mirror in an Agent Provocateur corset; reclining on her living room sofa in Hervé Léger.
Jenner is six-foot-two, and in heels she towered over everyone. She looked stunning. It was a jaw-dropping transformation.
They were cautious about taking her outside but did for one shot, in her Porsche—a gift from Kris Jenner from when they were married—parked in front of her garage and blocked by a truck. What would turn out to be the cover image was shot in front of a painted gold wall, with Jenner in a custom-made, satin, corseted bodysuit.
We stayed out of Annie’s way—the first rule on an Annie shoot is to stay out of her way. We knew what a historic photo shoot and story this was.
At one point we saw the security guys outside stir—something was going on. They gathered together and focused their binoculars on the same location, down the hill toward the Pacific. A few moments later, Keith came in and approached us, looking concerned. “There’s a Bentley coming up the hill.” He paused for a moment. “Kim.”
This was a problem, a potential security breach. Kim Kardashian can’t make a move without paparazzi on her tail. What if she was followed? This put the whole carefully planned operation in jeopardy. It was an unexpected visit but not one that was a surprise. Annie Leibovitz was here photographing her stepfather for what would surely be an iconic cover of one of the world’s most famous magazines, and she wanted in.
Kim pulled up to the house in her Bentley. She went through the same security checkpoint we had. Her cell phone was confiscated. And just like that, Kim Kardashian was in the house.
Kim is not tall, a few inches over five feet, and is curvier than the winding mountain road she drove in on. She has what can best be described as an hourglass figure, but an hourglass that counts a significantly longer period of time than a single hour. An oval line traced her face, where the thick coating of makeup began and ended. Kim was camera ready.
Vanity Fair and the Kardashians didn’t have a relationship. In fact, we had an unofficial ban on any Kardashians appearing in the magazine. We took a stand. None of them had ever been invited to the Oscar party. It was a cultural cold war. And no one was happy to see her on this day—she was a distraction, could throw off the energy and connection between photographer and subject that makes for great photographs.
Buzz and I were tasked with running interference, keeping her out of frame and occupied while Annie snapped away. We introduced ourselves, led Kim to the kitchen, and sat on stools around Caitlyn’s kitchen counter. With no reality-TV cameras around, she seemed relaxed; she was just Kim, a normal human being, albeit one of the most famous women in the world whose equally famous stepfather was in the next room in heels and a wig, not to mention with new breasts, being photographed as a woman for the first time ever.
Kim said she was proud of her stepfather, excited for the world to meet Caitlyn. But she was less interested in us than she was in getting into one of Annie’s photographs. She would turn her head often, toward the voices and popping of strobes coming from the other room. Eventually it became clear Kim wasn’t going to be photographed that afternoon, Annie wasn’t taking the bait, so she decided to leave.
How do you do a secret photo shoot with Annie Leibovitz and Bruce Jenner, in a dress and heels, without something leaking?
A few days later, now back in New York, Buzz e-mailed me his story using some fancy encryption application to protect it. It was more than 11,000 words, which is long for a magazine piece, especially in 2015. It was perfect.
The photographs came in soon after. They were astounding. Annie had triumphed. Caitlyn was completely transformed and looked as stunning in the photographs as she had the day of the shoot. Graydon hadn’t seen any Polaroids or stills, which were forbidden in case one leaked, so he had no idea what to expect. His jaw hit the floor.
I thought back to that moment when he told Jane to “reach out to Bruce Jenner and offer him a cover.” Unbelievably, it happened, but more so as documentation of one person’s journey to finding, revealing, and embracing their true self.
With story and photographs in hand, the next challenge was putting them together while keeping it a secret from the staff, although by this point it was a pretty open secret. But we couldn’t take any chances.
We papered over the window of an interior office and created a base of operations to which I had the only key. We put two computers in there that weren’t hooked up to the Internet or the internal editorial system. This was the only room where the story and the photos would be, and only eight of us would have access to it. I spent the better part of two weeks in there.
Chris Dixon, our creative director, would come in to work on the 22-page layout and the cover. Graydon and Jane would sit with Chris to review everything. I had a dedicated copy editor and fact-checker for the piece. Any changes or questions I had for Buzz were done over the phone. Nothing was to be e-mailed.
When it came time to put the cover together, we went back and forth on the image, settling on the shot in the satin bodysuit in front of the gold wall, the Vanity Fair logo in a simple and elegant black. Next up were the cover lines. Did we need Bruce Jenner’s name on there? Would anyone know who this was? In the end we decided to leave the name off. Bruce Jenner was gone for good. She was now Caitlyn Jenner.
We landed on three words, in quotes: “Call me Caitlyn.”
Ellen Kiell, our assistant managing editor, flew to the printer in Lexington, Kentucky, with the file containing the cover and story. We sent our own security team to the printer to safeguard our precious cargo. And then we waited anxiously.
On June 1, 2015, we were ready to go. We were rolling out the cover, a few images, and the first few paragraphs of the story online before the issue hit newsstands. A few of us, including Graydon, Jane, Jessica, Digital Director Michael Hogan, and our P.R. director, Beth Kseniak, gathered in the conference room a little after noon. We had the Web site’s traffic numbers projected onto the conference room’s big screen, so we could see the results in real time. At 12:30, Mike hit the button.
It took a few minutes for the numbers to start moving up. They went slowly at first, then started ticking up a little faster, then, like an avalanche, they began to increase rapidly. At the 15-minute mark, the numbers began moving up so fast we thought the machine might break, if such a thing were possible. Twenty minutes later, we had more than a million people on our Web site, and the numbers weren’t slowing down.
The Caitlyn story brought nine million unique visitors to our Web site in the first 24 hours, a company-wide traffic record. It had 3.9 billion social-media impressions, whatever the hell that actually means. That day, Caitlyn Jenner was the only news that mattered.
Dana Brown is a writer and producer and a former deputy editor for Vanity Fair