Vanity Fair features editor Jane Sarkin orchestrated Caitlyn Jenner’s debut on the magazine’s May cover and Jessica Diehl engineered her fashion transformation. Here, they explain how it all happened.
Jane, how did the Caitlyn Jenner story come about?
In November 2014, Graydon [Carter] said to me, “I hear all this stuff about Bruce Jenner.” At this point [his transition] wasn’t in the news a lot, just that he was a cross-dresser. And he said, “Let’s try to get him for a shoot and interview.” My kids would watch the Kardashian show and I thought he was the one interesting person on it. I tried to contact him, but he didn’t have a contact besides the show’s people. [I found his] sports agent and immediately he sent me back an e-mail saying, “Sorry, he can’t do this story. It makes him sound horrible.” And that was the end of it. But I never stopped there. I tried to poke around about ways to get to Bruce Jenner. No one was getting back to me. In early January, an old friend of mine, [Jenner publicist] Alan Nierob, whom I’ve worked with on many covers, called me and said, “I hear you’re interested in doing a story.” I asked, “Is it Bruce Jenner?” and he said, “I can’t believe you just said that.”
He was shocked that I knew. He has known Bruce a long time. He said to me, “We would like you to do the first cover of Bruce Jenner as a woman.” He told me Diane Sawyer would have the only interview with him before the surgery, as Bruce Jenner, and we would have the first photos as a woman. We immediately knew Annie Leibovitz would do the shoot, and we were so fortunate to have Buzz Bissinger to write the story. That combination was unbelievable. Buzz had unprecedented access to Bruce and then Caitlyn. We were the first ones to reveal the Caitlyn name. It was all supposed to come out on the cover of Vanity Fair, which was really hard to imagine. How are we going to keep it under wraps? We had to do it very secretly. I’m sure there were a few people who say they knew about it, but no one was talking and no one said a word. We were in lockdown here. We wouldn’t do anything online. Everything was offline.
So no e-mail then?
No e-mail. It was very exciting because it was done in an old-fashioned way. No e-mail. No texting, nothing electronic at all. The photos were kept under lock and key, which is usually where you get a leak. We had security at the printing plant, and we had crazy security at the shoot. It’s funny now that I think about it; the whole shoot at Caitlyn’s home is on the top of a mountain in Malibu. That itself was security. There are a lot of paparazzi around, but they can’t get close enough to her. She stayed in that house. She said she did not reveal herself until we came out with that cover.
How many months was she waiting?
We didn’t do the shoot until May 5, and the cover came out June 1. She did her interview with Diane in February, then she went away and had surgery, and she recuperated in that bunker-like house with the most beautiful views, but it was a prison for her. I think she got used to that. She could stay in there and not go out into the world; she wasn’t ready. And then our cover gave her the ability to go out into the world.
Was the plan always to release it on a Monday?
Graydon said, “The Internet is newsstand. We all know it. Let’s not fight it. Let’s go for it.” He said to release it on June 1. We were ready to go Saturday or Sunday if it leaked. It started to leak, but not really. By noon on Monday, it was out. It was really exciting to do it that way.
Who chose Buzz to write the story?
Graydon picked him. Buzz understood the whole athletic side. This is a very complicated story. The greatest athlete in the world, 1976 gold medalist, and 40 years later, he’s become a woman. And Buzz is also a cross-dresser. He knew about Bruce Jenner, the Athlete, and Bruce Jenner, the Television Personality. He even says he never had a story like that. It’s the most amazing story he has ever done. He was able to spend hours and hours with Caitlyn. I don’t think there was anyone better to work with than Buzz. He had a real sensitivity for the subject. He got along really well with the family. Caitlyn was fantastic with him. She became very open.
How did you prepare for the shoot?
Annie had a vision of how she thought it should be, and she wanted it to be an extremely easygoing time, even though it was a very important subject for her to portray correctly. We worked really hard on the setups of the shot. Jessica Diehl did the clothes, and she had her own vision. We had the greatest hair and makeup team. It was teamwork at its best.
What was the shoot like?
Nowadays you’ll have two hours, but we had two full days. That first morning we all met with Annie in a makeshift production office in Caitlyn’s house, and she gave a pep talk: “This is a very historic moment, this is a very emotional moment, this is a very important day.” And it was really emotional for everybody. And that very first shot, where she walked out of her room in a black gown, was the first time she had seen herself. All the people around her were crying because it was the first time that she actually saw what she wanted to see in the mirror.
How many people were there?
I would say 20 people. Everyone gave up his or her cell phones. No selfies, no Instagram, nothing. Everybody knew going in that this was top-secret, and we all wanted it to have a big reveal. If it had gotten out, it really would have messed up everything.
Who enforced the no-cell-phone idea?
Graydon did. We have a security team that we use for our Oscar party and the Washington Correspondents Dinner, and they’re top-notch. We met with them and said this is how it has to be: Everyone has to give up his or her phone, from Annie down. Except Caitlyn didn’t. She didn’t have social media, anyway.
Caitlyn launched her Twitter account the same day the magazine came out.
It broke every record ever.
How were the sales of the issue?
I would say up 200 percent over any cover we’ve done recently.
In Caitlyn’s documentary series on E!, Graydon mentioned that your managing editor physically brought the issue to the plant.
We decided that the only way to ensure it wouldn’t leak was to send someone to deliver the plates to the plant, instead of sending it by FedEx or carrier. She went with it and watched it being printed. They were under strict instructions at the plant, and we had security guards there. We tried to think of everything.
Who in the office knew about it?
A core group of people knew about it, but we were just trying to protect everyone. We didn’t want anyone to leak it by accident. The less people that knew, the better. You did not want to be that guy or that girl that leaked the story.
Did you have a “fake” cover to avoid suspicion?
Yes, it was Channing Tatum. He was an amazing sport about it because we couldn’t tell him what was going on. He’s the greatest.
Have you ever done anything like this before?
I did the Suri Cruise cover. It was a while ago, but at the time, that was the big story.
How did you keep that story from being leaked?
In 2006, we didn’t have the social media problem. Annie and I went to Colorado with security. We had security at the plant again. I kept the story under lock and key. It was a different time.
Was choosing Caitlyn’s cover image difficult?
No. Any one of those photos probably could have been the cover. But this was the one where she really looked exactly how she wanted to look. We knew at that moment, Oh, my God, there it is.
It was so powerful to not have any other cover lines besides “Call Me Caitlyn.”
I think it was such an iconic image and historic story. We made it feel very important. We caught this whole transgender moment. All of a sudden, there she was.
Have you heard from Caitlyn since?
I went to the ESPYs. She’s thrilled. When she said, “Winning a gold medal was a good day, but these last two days have been the most meaningful.”
Did you cry?
Oh, yeah. I could cry now. I think it worked so well because she was so open about what she had done and how she wanted to be. For me, it wasn’t a very comfortable situation to meet her for the first time. I was really nervous. And she made it feel comfortable: “This is my life, and I’m Caitlyn.” It was an experience that I will never forget.
What do you think the story means?
I think it means that everyone can be comfortable in their own skin. She’s making it easier and helping that process. She’s at the forefront trying to help people. I think that’s a message she’s trying to give. And we tried to help her to help people.
Jessica Diehl, Vanity Fair Fashion and Style Director
What was your reaction when you first heard about the story?
I immediately just thought it was great. I found it timely and very important. And what I thought was great about it was here’s this man, who’s incredibly successful in one way, a gold medal winner, pretty major in my book. And he comes to Vanity Fair to put this out into the world.
Are you good at keeping secrets?
Yes and no. It’s very difficult for me, especially if something’s positive. So if you’re my friend and you tell me, “Please don’t tell anyone,” I can keep that secret, that’s no problem. But something inspiring and something brilliant? I have to say that was really difficult.
How many months did you have to keep quiet?
March until June, which is a long time. Another editor in chief told me, “I heard you’re doing this.” I had to bald-face lie to him.
What kind of woman were you creating?
When I first met Caitlyn, a month before we shot her, I went to her house to get a sense. I have nothing against the Kardashians. I think they’re fabulous and amazing. They take fashion to the next level. But it was really important for me to figure out that Bruce-slash-Caitlyn is someone who grew up in the ’50s, ’60s, and ’70s. Her thought process around style was much more American. [Vogue’s fashion director] Tonne Goodman would have loved it. She would have been Caitlyn’s style icon. I thought about Lauren Bacall or Lauren Hutton. It ain’t no Doris Day. Caitlyn’s quite fearless.
Who else did you work with on this besides Graydon, Annie Leibovitz, and Jane?
[Fashion market director] Michael Carl knew. I knew he wasn’t going to talk. My assistant, Ryan Young, also knew. The three of us went shopping, and it was hysterical. I’ve never had more fun in my life.
It’s really bizarre going to Saks, Bergdorf’s, and Barneys and trying to find certain sizes, which are never on the floor. There were three of us who don’t look that size and I was shopping, supposedly, for my “great-aunt” who was receiving an award. We weren’t sure if some looks were going to fit, so Ryan would go in the dressing room and try them on. He was really into it! The most amazing part was that nobody in the department questioned it. Even when I said she has a size 13 foot, wide. They all knew I was lying, but they knew enough to not ask. On the other hand, I thought, “What do you do if this is your life? What do you do if you’re transgender and you want to buy women’s clothing?” Going into department stores is not only daunting for a woman who isn’t a size zero, but there’s no escaping from the eyes of the sales staff. The coolest thing about New York is that nobody batted an eye.
Did you have a code name for Caitlyn?
Barbra Streisand. I thought it was the same generation. I thought she was really tall, maybe because I saw Yentl, and she’s not.
What was the shoot like for you?
I don’t really get super emotional about stuff, except this one. What was really stressful was the idea of building from scratch. Her wardrobe a month before the shoot was minimal, minimal, minimal. It was not my taste or even hers. It was more what was available. How can we have a couple things that make the wardrobe real? Have a bit of Max Mara, Tom Ford, a Balmain blazer. Have a bit of fashion and create a cohesiveness in tune with who this person is.
What did you think of the reaction to the story when it hit the web that Monday?
I was thrilled for her because the most important thing to her was for it to be received in an open way and be part of the dialogue. What was so brilliant was that it was a monthly that broke news in a manner that hadn’t been done in quite some time. Not many publications can do that. Vanity Fair has the trust of people to tell their story and to do that at their own pace.
Have you kept in touch with Caitlyn?
Yes! We were texting in the morning when the issue came out. She couldn’t believe it. She really was sequestered in her house. The reveal of Caitlyn wasn’t meant to be in the hands of the paparazzi but in a controlled and dignified manner. It was her coming-out party!