Caitlyn Jenner, photographed in her Malibu home. “If I was lying on my deathbed and I had kept this secret and never ever did anything about it, I would be lying there saying, ‘You just blew your entire life,’ ” she says.
Photograph by Annie Leibovitz; Styled by Jessica Diehl.
On March 15, the day of the Los Angeles Marathon and myriad street closures, Bruce Jenner left his bunker-style home above Decker Canyon in Malibu at 4:15 in the morning to avoid any possibility of being late. Detection seemed unlikely this early in the day; even the paparazzi go back to their wormholes for a few hours’ sleep before the body count begins again.
But anything could happen, as it had in January of 2014 in the space of roughly five feet from the back door of a medical office to the car, with Jenner’s neck in a bandage from a tracheal shave, his picture snapped and disseminated into the Internet infinity of insatiable gossip at warp speed. So the more nondescript the car the better, which is why the black 2014 BMW sedan, in the conspicuous consumption of Los Angeles, was inconspicuous.
Jenner had already been taking hormones. The hair on his body and his facial hair had been removed. He had had his nose fixed twice and the tracheal shave. On this Sunday his destination was the office of a surgeon specializing in what is known as facial-feminization surgery. Pioneered in the 80s and 90s by San Francisco plastic surgeon Douglas Ousterhout, it can involve such procedures as hairline correction, forehead contouring, and jaw and chin contouring. There would also be a procedure to augment his breasts.
Photograph by Annie Leibovitz.
The car made its way to the surgical center in Beverly Hills without incident. Jenner was nervous. He knew there would be pain, and he hated taking any kind of drug to alleviate it because of the way it made him feel. But there was more than just physical dread. Several days earlier I had walked with him as he played golf at the exclusive Sherwood Country Club, in Thousand Oaks. He has been a member there for 15 years, ever since Kris Jenner, feeling generous toward her husband, paid the roughly 5,000 initiation fee. He played by himself because he almost always played by himself, a loner who said he wasn’t lonely, although it was hard to see the difference. He didn’t take his game very seriously: he could have been a scratch golfer if he had. He often played two balls at a time, voicing the usual golfer epithets of “Sit!” and “Get down!” He liked the peace of it, the Santa Monica Mountains safeguarding the holes like a cupped hand. It was perhaps the only open space he could go to without getting besieged by the paparazzi, not only with their cameras hanging from their necks like evil eyes but also with their questions: “Are you a woman yet?” “Do you still have a penis?”
“You wonder if you are making all the right decisions,” he said as he played in the anonymous uniform of blue sweater and gray slacks and hat and sneakers, parring the 517-yard par-five second hole because he, as usual, drove it at least 280 yards off the tee, being the kind of athlete who can pick up anything instantly. “I wish I were kind of normal. It would be so much more simple.
“The uncomfortableness of being me never leaves all day long,” he continued. “I’m not doing this to be interesting. I’m doing this to live.” Given his sense of humor, he couldn’t resist adding, “I’m not doing this so I can hit it off the women’s tee.”
After all the confusion and shame and self-conflict and dishonesty for virtually all of his 65 years, was this the right decision? Could he go on living as he had?
He was not having genital surgery. There are an estimated 700,000 transgender women and men in the United States; only about a quarter of transgender women have had genital surgery. There is a common misperception that such surgery is somehow “required” to be a transgender woman or man, akin to a certificate from the Transgender Licensing Board. The transgender community for years has been trying to get the public to understand that genitalia are not a determinant of gender: you can be born a woman with male genitalia, just as you can be born a man with female genitalia. In any case, under the World Professional Association for Transgender Health’s “Standards of Care,” formed by a consensus of leading psychologists and medical specialists, genital surgery is not advised for at least a year after transition.
Jenner had actually gone through various stages of transition once before, in the mid- and late 1980s. He took hormones that resulted in breast growth and had his beard removed through an incredibly painful two-year regimen of electrolysis that he withstood without any medication because “pain is kind of, for me, part of the pain for being me … this is what you get for being who you are. Just take the pain.”
The physical changes had been so noticeable that rumors started, including a call from The New York Times about what was going on with Bruce Jenner, in particular Bruce Jenner the winner of the gold medal in the decathlon in the 1976 Olympics, a symbol of masculinity as interwoven into American culture as the Marlboro Man.
Jenner had once talked in jest about going to Denmark and coming back to his four young children as Aunt Heather. It was obviously a bizarre thought, indicative of his terrible confusion. It also could be seen as a precursor to the fractured relationship that would occur when he essentially lost contact with the four children from his first two marriages, eventually in favor of yet another new family, with values that had once seemed so alien to his, the Kardashians.
He was living in a one-bedroom house in the Malibu hills in almost total seclusion after he started to transition in the 80s. Dishes piled up. His career was in limbo after an income of half a million dollars the first year after the Olympics. Everything had seemed perfect then, or as close to perfect as it can be when you are pretending your way through life, conforming to the vision of millions because that’s what they expect, and that’s exactly what you give them because you are good at it, scary good. ABC executive Irwin Weiner had offered him a broadcasting job the very same night as his Olympic victory, in Montreal. He tried out for the lead role in the film Superman, which was too much of a stretch without acting experience, although Jenner was actually one of the great actors of our time. He adorned the front of the Wheaties box. He drank orange juice for Tropicana and took pictures for Minolta. He gave speeches about the 48 hours of his Olympic win all over the country to enthralled audiences. He was red, white, and blue. He was Mom and apple pie with a daub of vanilla ice cream for extra deliciousness in a country desperate for such an image. He had a tireless work ethic. He had beaten the Commie bastards. He was America.
“Jenner is twirling the nation like a baton; he and his wife, Chrystie, are so high up on the pedestal of American heroism, it would take a crane to get them down,” wrote Tony Kornheiser in The New York Times in 1977.
He also secretly wore panty hose and a bra underneath his suit so he could at least feel some sensation of his true gender identity.
He stopped transitioning in the late 80s. He was scared of what the reaction would be. He decided he could not do this to his four children, Burt, Cassandra, Brandon, and Brody. He needed to jump-start his career. He needed credibility to squelch the rumors, and he told me marrying Kris Kardashian, in 1991, helped give him that along with compatibility and love.
“That was a good day,” she says of winning gold, in 1976. “But the last couple of days”—being photographed as Caitlyn by Leibovitz—“were better.”
Photograph by Annie Leibovitz; Styled by Jessica Diehl.
In March, he had been living on his own for about a year and a half since his and Kris’s separation, which would ultimately lead to their divorce after 23 years of marriage. It gave him the opportunity to live more freely as a woman. It wasn’t enough. He worried the most about how the two daughters whom he and Kris share, Kendall and Kylie, would react to his transition. But Kendall was a 19-year- old supermodel, and Kylie, at 17, already had endorsement deals for various beauty products, in addition to what they make from Keeping Up with the Kardashians, on the E! network. They were each independent enough to have bought homes, Kendall a condo for .4 million in the area of Westwood, Kylie a house in Calabasas for .7 million. Now that he felt the two girls could process the change, there was only one step left.
Bruce Jenner went to the office in Beverly Hills, thinking the facial-feminization surgery would take about five hours. Caitlyn Jenner left the office in Beverly Hills after the procedure had taken roughly 10 hours.
Comfort in Isolation
During the first full day of recuperation, there was a moment when Caitlyn Jenner lay down on her bed as best she could, hoping to get some sleep. The pain was such that she had no choice but to be on large amounts of medication. She had ice packs over her eyes. She closed them for a little bit, then suddenly shot up, causing the ice packs to slip. She was undergoing something that had never happened before in 65 years of life: a panic attack. She told the 24-hour nurse on duty she had to get out of bed. Caitlyn asked her to turn on the television so the sound would be a distraction. The recently purchased .6 million home—built with concrete slabs like the artillery batteries you can still see on the Pacific coast, put there in case of a Japanese attack during World War II—was one floor on top of an aboveground garage. There were three bedrooms off the long hallway and then the kitchen and dining area and sunken living room in an open floor plan. It offered remarkable views of Catalina Island and the Pacific and glimpses of whales through the floor-to-ceiling windows in her bedroom. Because of its literal mountaintop location, you could see everything but not hear anything except the flapping-flag sound of the wind. No nearby neighbors. No cars pulling up. It was encapsulated in silence, and maybe that was the point of living there, comfort in isolation.
Caitlyn went into the long hallway and paced back and forth on the dark wood floor, where not even the footsteps made a sound. The panic attack lasted about 15 seconds, but a single thought continued to course through her mind: “What did I just do? What did I just do to myself?”
A counselor from the Los Angeles Gender Center came over to the house so Caitlyn could talk to someone with professional expertise. The counselor helped ease her mind. She said such reactions were often induced by the pain medication. She also said such second-guessing was human and temporary. The thought has since passed and has not come back. There is no buyer’s remorse. Not that it matters anyway, because there is no turning back.
“If I was lying on my deathbed and I had kept this secret and never ever did anything about it, I would be lying there saying, ‘You just blew your entire life,’ ” she told me. “ ‘You never dealt with yourself,’ and I don’t want that to happen.”
Bruce Jenner, she said, was “always telling lies.” Caitlyn Jenner, she said, “doesn’t have any lies.” Bruce Jenner caused hurt to four children who loved and idolized him before he gave his love and total attention to another family. Caitlyn Jenner has the possibility to make it right and close the fissure as much as she can. “I have high hopes that Caitlyn is a better person than Bruce,” said his oldest son, Burt, now 36. “I’m very much looking forward to that.”
“It Ain’t Bruce”
This is the most remarkable story I have ever worked on in 38 years as a journalist, the only writer in the world with unlimited access to Jenner for a story of global interest, witness to the final months of one of the most iconic male athletes before he disappears and a woman appears in his place. I spent hundreds of hours with the man over a period of three months. Then I spent countless hours with the woman. It was initially weird, and virtually anyone who says it isn’t weird is giving themselves far too much credit. It was initially surreal, having seen Bruce Jenner set seven personal bests as he won the decathlon in 1976 with that perfectly buff body, and seeing him now in an elegant black dress with fine-looking breasts. With apologies to members of the transgender community, who are rightfully sensitive about the use of language, I constantly used “he” instead of “she,” and at one point called Caitlyn “dude” out of force of habit, and closed conversations with “All right, man, I’ll talk to you soon.”
“I don’t really get hung up,” she told me. “A guy came in the other day and I was fully dressed—it’s just habit, I said ‘Hi, Bruce here,’ and I went, Oh fuck, it ain’t Bruce, I was screwing up doing it.”
My miscues have nothing to do with intolerance—I have been a cross-dresser with a big-time fetish for women’s leather and an open critic of the often arbitrary delineation between men’s and women’s clothing—but because it is a strange story regardless of all the important inroads that have been made by transgender men and women into the cultural mainstream. Just as it is a tragic one, and a painful one, and a harmful one, for so many years, not just to himself but to others he should have been closest to, and a lonely one, and a brave one, and a funny one, and maybe, just maybe, because it is far too early to tell, a triumphant one.
The Show Must Go On
Or maybe, given Jenner’s past, it’s all just fodder for a “docu-series” (i.e., reality television in a fancy suit) that, in May, Caitlyn started shooting for the E! network, debuting this summer. Can you hear the thunder of a Kardashian spin-off? The same four children whom he lost contact with for years at a time, none of whom have the last name Kardashian, fear exactly that. They also fear that the spectacular way in which she came across on the ABC 20/20 special two-hour interview with Diane Sawyer (Caitlyn had completed her transition by the time the show aired, on April 24) will endanger what she can do for the continued momentum of the transgender movement. Instead they worry that the whole narrative will devolve into spectacle and shenanigans intercut with a little dash of social cause and the use of paid consultants who are experts on transgender issues as a cover for social responsibility. She is also someone who in the past has been easily influenced by the opinions of others. Caitlyn insists that will not be the case since, as an executive producer, she has full creative control. Her insistence is real.
The children, collectively known as “the Jenner side” and all in their 30s and as grounded as the Kardashians are not, feel otherwise. Through the portal of their television show, the relationship of the Kardashian children to their dad has unfolded publicly for eight years. The relationship of the Jenner children with their dad has gone untold: unless you were a Keeping Up with the Kardashians fetishist, you might not even know that he had four other children. Given the pressure placed on them to participate in the upcoming E! series, it became clear to me that their story is more germane than ever.
They disagree with their father’s decision to use not only the same production company that made Keeping Up with the Kardashians but many of the same people, including several original executive producers. The E! network, with such shows as Keeping Up with the Kardashians, Total Divas, The Royals, and Botched, is not known for its subtlety. In the hope of repairing their relationship with their father, they—Brandon in particular—have supported Caitlyn, and that support has been inspiring to her.
The last thing the Jenner kids want to do is reverse the rebuilding of the relationship. But despite numerous entreaties from their father as well as the head of E! programming, the Jenner children refuse to participate, forgoing financial gain and exposure in the process. At first their decision did not seem to register with Caitlyn. She kept hoping they could be persuaded because she knows from eight years on Keeping Up with the Kardashians the necessity of a family dynamic for ratings success. When she realized the decision was final, she became increasingly frustrated and on one occasion hurled profanities. She told me she felt “terribly disappointed and terribly hurt.”
Caitlyn neither understands the tragic irony of those words nor recognizes her historical tendency toward self-victimization. Based on hours of interviews with the Jenner children, as well as his two ex-wives, a picture emerges of a father who had been absent for years at a time, insensitive, hurtful, and weak in no longer making an effort to keep up contact after he married Kris Kardashian. Caitlyn openly acknowledged to me mistakes made with them as Bruce Jenner. The regret is genuine. Juggling two ex-wives with a third wife was at times very difficult. But not seeing his children for long periods, beginning around the time of their adolescence, not acknowledging birthdays, not going to graduations, and intentionally not being there for the birth of his daughter were Jenner’s own decisions.
The wounding only went deeper, given that Bruce Jenner was an exemplary father to the so-called Kardashian side, including Kendall and Kylie.
In the course of their father’s journey, the Jenner children have gone through their own journey as well. “Love has nothing to do with gender,” said his daughter Cassandra. She paused for a moment and added this: “There’s no way to separate what he’s going through, the trap he’s been in for the past 60 years and how that has affected his choices around love and relationships. It’s impossible.”
Light and Shadow
About two weeks after the surgery, I sat on a stool at the kitchen counter opposite Caitlyn. She had listened to Monica Lewinsky’s powerful TED talk on what it is like to be the ceaseless target of cyber-ridicule. The talk had struck a chord with Caitlyn because of the similarities with how she had been dealt with on the Internet. She had in front of her five pages of notes. It dawned on me that she was going to give her version of a TED talk to an audience of one: me.
It went on for nearly 40 minutes. My heart bled for Caitlyn. She was so earnest, trying so hard: you could feel the essential goodness in Caitlyn, and Bruce Jenner before her. Mistakes had been made, ones that caused terrible scars, but as many others had said about him, they emanated from following a path of least resistance as well as from a hatred of confrontation.
Bruce was instantly likable, a singsong lilt in a voice of amusement and bemusement, shades of sweet goofiness. It was how he liked to interact, bouncing along the surface. But it seemed like he often used the method of communication as a guard against emotional connection.
“If he had emotional legs he’d get up and walk to you,” Jenner’s second wife, Linda Thompson, remembers telling her son Brandon after his father had not attended his high-school graduation. “But he doesn’t. He just doesn’t have that capability.”
It was late afternoon by the time the simulated TED talk ended. Light streamed in through the kitchen bay windows, slanting through the bottle of handwash onto the porcelain sink and the Wolf stove and the Sub-Zero refrigerator. The clarity was piercing, only adding to the stillness, relics of an archaeological expedition, a remodeled kitchen untouched by human hands discovered in the hills of Malibu. The light then suddenly shifted. It angled on her face in a perfect dissection of brightness and shadow down the centerline. Caitlyn looked gorgeous in the light. Her features were accentuated and popped. Just as her features were obscured in the shadow. I did not know which way it would go. Only where it had already gone.
“Nature Made a Mistake”
When Jenner’s sister Pam was a young girl she noticed something puzzling one day on the bookshelf of the family’s house, in Cornwall, New York. It was the mid-1950s, and like millions of other American families in the 50s the Jenners had a set of encyclopedias. What was odd to Pam was the way in which her brother Bruce, 16 months younger, had arranged them: from A to Z, right to left. She noticed how her younger brother spelled “saw” as “was” and “was” as “saw.” Pam concluded, as would just about any older sibling caught up in her own world, that Bruce was just “a stupid younger brother.” Their mother, Esther, was puzzled. When she worked on spelling with her son she noticed that he spelled every word right one day and then completely forgot the next. “Bruce, you’re not concentrating. You’re daydreaming,” she said to him. In second grade, since he still could not read, he was held back. Teachers thought that the child, whose father, William, was a tree surgeon, was just lazy.
It was only later that Jenner was diagnosed with dyslexia, a learning disability marked by difficulty in processing language. He wasn’t lazy or stupid. He could spell every word right the first time because he had memorized them. His self-esteem as a child was understandably poor. Dealing with his dyslexia was enough of a challenge for Bruce Jenner. It was enough for any young boy trying to navigate the rock-rimmed shore of peer acceptance. Jenner is fond of invoking God in setting out the challenges of his life. If that is the case, then God had a daily double in store.
When Bruce was around 10, he would sneak into his mother’s closet, sometimes his sister’s. He would put on a dress and maybe wrap a scarf around his head and walk around outside. Without knowing the clinical term for what he was feeling—gender dysphoria—he found himself “fascinated by it all,” just as he felt “scared to death somebody was going to find out.” Because there was nobody he could talk to about it. He didn’t tell anyone until the early 1970s, when he told his first wife, Chrystie.
In the context of the late 1950s the very concept of a transgender woman in the United States was foreign, the only publicized experience that of Christine Jorgensen, a former World War II G.I. from the Bronx whose name at the time was George Jorgensen Jr. She underwent gender-reassignment surgery in Denmark because it wasn’t done in the United States. The story became public on December 1, 1952, after the New York Daily News got ahold of a letter Jorgensen had written to her parents in which she said, “Nature made a mistake, which I have had corrected, and I am now your daughter.” The resulting publicity was astonishing but the interest largely prurient and centered on someone with a penis going to a foreign country and coming back with a vagina.
In fifth grade Jenner ran in a race, perhaps the most important sporting event in which he ever participated. He turned out to be the fastest kid in school. His athletic ability led him to football and basketball at Sleepy Hollow High School, and then Newtown High School, in Sandy Hook, Connecticut, after he moved there in the middle of 11th grade. It also exhibited itself out of school when he won the Eastern States water-skiing championship. “Sports saved my life,” Jenner said. He became popular because jocks are always popular. He became determined in sports because he was gifted, but also because it helped to prove his masculinity, since, as he told me, “that’s what everybody wants to believe.”
He went to tiny Graceland College, in Lamoni, Iowa, on a football scholarship. He hurt his knee, ending his football career. But a coach there, L. D. Weldon, who happened to be an expert in the decathlon, saw something in Jenner, and Jenner responded to it. He came out of nowhere in April of 1971 to win the decathlon at the Kansas Relays. He made the United States Olympic team in 1972 and finished 10th in the decathlon in Munich. After the end of the competition, 10 different events in two days, Jenner went on a long-distance run through the streets of Munich. It was the beginning of a training regimen in which he would practice eight hours a day, every day, for the next four years, leading up to the 1976 Olympics.
Going for Gold
The decathlon was perfect for him, not just as a sporting event and the ultimate in he-man-ism but also as a years-long diversion from the awareness that he identified as a woman. He hoped for much of his life that the gender dysphoria would somehow go away, be stamped out with enough diversions, or at least not occupy his thoughts: decathlon training, other sports after the Olympics such as professional car racing and tennis, becoming a pilot, marrying and having a family. “You always think in the back of your mind, I can live with this. I can fix this…. If I just do this it’s going to be O.K.,” he told me.
On July 30, 1976, in Montreal, Jenner won the decathlon, the most grueling event of the Olympics, at the age of 26, with a world record 8,618 points. Because of the times, a country struggling with the aftershock of Vietnam and the oil embargo and Watergate, he became a supercharged hero. The United States’ performance at the 1976 Olympics—where it won only one individual gold medal in men’s track and none in women’s track and was embarrassed by the Soviet Union and East Germany at the peak of the Cold War—only heightened the need. Tens of millions watched Jenner on television, buff and with that mane of hair flowing like a lion’s, running through the Olympic stadium holding a small American flag which had been handed to him by an overjoyed spectator.
He was six two and 194 pounds of mostly muscle, perfectly proportioned. “Bruce Jenner of San Jose, Calif., wants to be a movie or television star. After his record-breaking victory in the Olympic decathlon today, he probably can be anything he wants,” wrote Frank Litsky in The New York Times.
Although Litsky did not know it at the time—no one did, except for Jenner’s first wife, and she did not know the full extent—falser words could never be written. Becoming a woman wasn’t going to happen, because he had won not simply a gold medal but a gold medal in the decathlon, which carries with it the title of “the world’s greatest athlete.” Litsky went on to list the usual descriptive suspects—“a handsome, cheerful, outgoing man with long, straight blond hair.”
“People say, Oh my God, what a body—you look great. That wasn’t what I was looking for,” Jenner told me. “I could not really cross-dress. I tried to grow my hair out as much as I could without getting yelled at.”
The night of his Olympic win Jenner and his wife, Chrystie, stayed in a penthouse hotel suite in Montreal. It was arranged by his lawyer at the time, Alan Rothenberg, after he realized that the Jenners, typically, with their innocence and lack of lavishness, had made no plan for a place to stay.
After Jenner woke up the next morning, he walked past the grand piano into the bathroom. He was naked. The gold medal was around his neck. He looked at himself in the mirror. The grand diversion of winning the decathlon was finished. Everything would change. Nothing had changed. He didn’t see a hunk. He didn’t see success. Instead of reveling in the accomplishment, he diminished it in his mind because he had done it, the stupid little boy with dyslexia. The little boy who knew he had been born a girl and was now just trying to put one over on the rest of the world.
“Now what do I do?” he said to himself.
He was too irresistible for the starved nation, too perfect. He almost immediately signed a contract with ABC. He got taken in the seventh round of the National Basketball Association draft in 1977 by the Kansas City Kings. He did the endorsements and the speeches. He knew he was bullshitting. “Underneath my suit I have a bra and panty hose and this and that and thinking to myself, They know nothing about me.
“I walk off the stage and I’d feel like a liar. And I would say, ‘Fuck, I can’t tell my story. There’s so much more to me than those 48 hours in the stadium, and I can’t talk about it.’ It was frustrating. You get mad at yourself…. Little did they know I was totally empty inside. Totally empty inside.”
Jenner had married Chrystie Crownover in 1972. They had met in college. She was the daughter of a minister from southeastern Washington State. She suggested the marriage, in part because her job as a flight attendant for United Airlines gave her access to free tickets for herself and her spouse, so they could fly to decathlon events all over the world. In stark contrast to the Kardashian period, they drove under the redwoods of California with Beethoven blasting and grabbed a rope swing to drop into the Russian River. Chrystie was the breadwinner, a devoted partner in his journey to a gold medal.
In 1973, early in the marriage, Chrystie noticed a rubber band attached to the hook of one of her bras. She asked Bruce about it. She remembered him telling her, “Gee, I don’t know.” Subsequently he gathered the nerve and brought up the mystery of the bra again. “That’s why the rubber band. Because I’ve been wearing your clothes.”
Caitlyn in her bedroom. Brandon Jenner says he was a little taken aback when he met Caitlyn for the first time and she pulled up her top to reveal her new breasts. “Whoa, I’m still your son,” he said.
Photograph by Annie Leibovitz; Styled by Jessica Diehl.
“He told me he always wanted to be a woman,” Chrystie said. “He told me as a little kid how that felt. He told me [of] different fantasies that he had, related to loving women.”
Chrystie felt immense gratitude that he was sharing something so intimate with her. “If he had been wanting to dress up when he was with me or any of those things it would have been different. But he was still masculine. He was still my hero. He was still pursuing this goal of being the greatest athlete in the world. It wasn’t like it was a hard thing to handle. It was like a piece of information he shared with me and then he went back to being a real guy…. He had a strong, healthy sex drive and seemed like pure man.”
Bruce Jenner as Bruce Jenner had a sexual appetite exclusively for women. Caitlyn has no idea what the future will hold as Caitlyn Jenner. But, she adds, it is not important to her right now. “If you have a list of 10 reasons to transition, sex would be number 10.” It should also be emphasized that sexual preference and gender identity have nothing to do with each other.
In September 1978, Chrystie and Bruce had Burton, or Burt for short. He was named after Jenner’s younger brother, who had died in a car accident shortly after the Olympics, on the day he was supposed to fly to California to live with Bruce and establish residency in hopes of attending a state university.
The marriage began to fissure. They separated for a period of time, then got back together. Chrystie became pregnant; in an interview in Playboy in 1980, Jenner said, “My first reaction was that I didn’t want it,” and he asked her to consider an abortion. They separated permanently when Chrystie was still pregnant with their second child, Cassandra, who is now 34. She has two young children with her husband, Michael Marino, who is in private equity.
“I never knew he wasn’t at my birth until I was about 13 years old and we were arguing on the phone about money,” Cassandra, a 2001 graduate of Boston College and stay-at-home mother, told me. “He kept saying, ‘You don’t know the whole story.’
“I hung up the phone and was asking my mom what he was talking about until she confessed the history behind my birth.”
Jenner told me he was in the middle of divorcing Chrystie when he found out she was pregnant. He said he brought up the idea of an abortion but rejected it after 30 seconds. He was in a hotel room in Kansas City when Cassandra was born. He cried, but “under the circumstances I could not even see myself being there.”
Jenner started seeing Linda Thompson, a performer on the syndicated country-music and variety show Hee Haw who would go on to have an accomplished career as a songwriter. (She and her second husband, David Foster, co-wrote the song “I Have Nothing,” made famous by Whitney Houston.) Bruce and Linda had met at the Playboy Mansion during a tennis tournament. Jenner divorced Chrystie in 1980 and married Thompson several months later, in January of the following year. She was pregnant at the time with their first son, Brandon.
He appeared on the cover of Playgirl with Linda Thompson in May of 1982. He was shirtless (but not hairless). Linda, in what looks to be a low-cut leotard, has her lips and nose pressed sensually against his cheek. In a question-and-answer interview he talks about his “masculine qualities” and their healthy sex life and the fabulousness of their marriage after a year. It appears obvious in hindsight that he was desperately trying to maintain his cover in a society that still largely condemned transgender women and men.
They had been married for more than four years and had two children, Brandon and Brody, when he told Linda of his gender dysphoria. She said she was shocked and devastated. Brandon was about three and a half at the time and Brody 18 months.
They went into counseling, but, Thompson told me, the therapist said the condition would never go away. “ ‘You can live with him as he transitions and you can have what you might consider a lesbian relationship because, you know, you can stay married to him. You will both be women, but he’s attracted to you. He would like to stay married to you. Or if that doesn’t appeal to you, you can move on.’
“And I opted for the latter because I married a man…. As much as I felt my life and my dream were destroyed and I was going to have to get a divorce, and then my kids, I was going one day to have to explain to them—I thought my pain doesn’t compare to the pain that he’s in. At least I’m comfortable living in my own body.”
Jenner describes the period of the mid- to late 80s as “the dark years.” He had no social life. Professional opportunities dwindled, in part because he had no motivation to work and didn’t seem to care. He had moved from ABC to NBC, and around 1983 his contract was not renewed. He was tired of giving speeches. His acting career had resulted in one feature film, back in 1980: Allan Carr’s frantic Can’t Stop the Music, a thoroughly bizarre film with Steve Guttenberg and Valerie Perrine and the Village People trying to capitalize on the disco era. Its campiness is so bad that it’s sociologically fascinating to watch today. But it received the 1980 Razzie for worst picture and screenplay; Jenner was nominated for worst actor but lost out to Neil Diamond, for The Jazz Singer. A made-for-television film, Grambling’s White Tiger—starring Jenner as a white quarterback on the otherwise all-black Grambling State University football team, with Harry Belafonte as legendary coach Eddie Robinson—was well received. But it did not propel him anywhere.
He was running out of the diversions that had guided his life. But the gender issues were not going away; if anything, they were intensifying. “The gender issues were big at that time,” Jenner told me. “I had ignored them for so long, but I was aging.”
“I Don’t Want to Be This Way”
It was during that first attempt at transition, in the mid-and late 1980s, that he went on hormones, had his beard removed, and had plastic surgery on his nose. The changes were noticeable. Brody Jenner, now 31 years old and a reality-TV staple with a new show called Sex with Brody, debuting on E! this summer, was somewhere around 4 when he said to his mother, “Mommy, we saw Daddy get out of the shower and he’s got boobs.” Rumors began in the media and were squelched. “I was terrified of being discovered,” Jenner said. “I was not at a point in my life where I was comfortable with myself.
“ ‘I don’t want to be this way’ was the bottom line. Who would want to be dealing with all these issues…. I look at men and say, Oh my God, would it not be so wonderful to be comfortable in your own skin, male or female, so when you wake up in the morning you get dressed and go to work and this identity issue is not even present?
“You’re happy being who you are. You have a beautiful wife and this and that…. I look at women and think the exact same thing: Wouldn’t it be wonderful to wake up in the morning and be able to get dressed and go out and live your life?”
But the context of the times made Jenner scared. There were only a handful of well-publicized transgender cases. The atmosphere for transgender men and women was still extremely difficult. Johns Hopkins Hospital had come to public attention for championing sexual-reassignment surgeries in 1966 but stopped doing the procedure 13 years later, after a controversial study by a psychiatrist there reported that recipients, in making psychosexual adjustment, were no better off than those who didn’t have the surgery. Paul McHugh, psychiatrist in chief for the medical school, whose stance against gender-reassignment surgery borders on religious zealotry in the eyes of activists, was instrumental in the decision, concluding that the only surgery as radical and misguided was the lobotomy.
The same year, 1979, Professor Janice G. Raymond published The Transsexual Empire: The Making of the She-Male. She wrote in the book, “I contend that the problem of transsexualism would best be served by morally mandating it out of existence.”
Enormous strides are being made today in the acceptance of transgender women and men, thanks, in part, to the Golden Globe Award-winning Amazon series Transparent and such transgender spokeswomen as the writer Janet Mock and Orange Is the New Black star Laverne Cox. (Last year Cox appeared on the cover of Time magazine with the headline THE TRANSGENDER TIPPING POINT.) Yet only 19 states have laws to protect transgender workers.
Around 1990, Jenner stopped his transition. He decided he needed to “get back in the game.” He was in Ketchikan, Alaska, finishing a celebrity fishing show with former Los Angeles Dodgers first-baseman Steve Garvey, when Garvey’s wife, Candace, raised the idea of fixing him up with Kris Kardashian. She was divorced from Robert Kardashian, who went on to fame—or perhaps infamy—as a friend and attorney of O. J. Simpson’s and died of cancer in 2003, at the age of 59. Candace mentioned that Kris lived in Beverly Hills with a marvelous sense of style and great shopping skill. Jenner at first was not interested. “I’m thinking the last thing I need is a Beverly Hills shopper,” Jenner said. “I don’t need that. No offense to shoppers. It’s the perception of this woman who sits around Beverly Hills and goes shopping all day.” On second thought, Candace said, it would never work since Kris, like Jenner, had four children. Then Jenner was interested: “She comes with as much baggage as I do.”
They hit it off immediately and seven months later, in 1991, were married.
The issue of how much Bruce Jenner told Kris of his gender-identity issues is a matter of dispute: neither side wants to appear rancorous, but the two sides agree on virtually nothing. Breast growth as the result of hormones is irreversible. Jenner insists that he was a “good solid B cup” when he met Kris. She said it was comparable to a “little bit of a man boob situation” but that there was “no B cup going on.”
The issue goes to the core of how much moral obligation Jenner, or anyone with established gender dysphoria, has to tell a prospective spouse of his or her condition. “When I met Bruce,” Kris said, “he told me that he had done hormones back in the early 80s. This was a conversation that took place in the early 90s. So, what he was telling me happened a decade earlier, and he never really explained it.” As far as Kris Jenner was concerned, “there wasn’t a gender issue. Nobody mentioned a gender issue. Somebody mentioned that [he] at one point in his life liked to dress up.”
Jenner is emphatic that he told Kris he had taken hormones in the late 1980s up until the year they met, and was equally emphatic in saying there were other side effects besides breast growth. He finds it implausible for her to suggest she was not aware of his gender struggle. But he does concede that “probably a mistake I made was maybe not having her understand—not the severity of it but that this is a condition you cannot get away from. From that standpoint maybe I blew it away a little bit, sort of ‘This is what I do.’ ” He said he did cross-dress in front of her. But ultimately, he said, she set down rules: he could cross-dress when he was traveling on his own but not at home.
Kris said he never cross-dressed in front of her, the only evidence “a few times I would see a suitcase or things lying around the house.” She also said she never set down any rules.
At first, based on interviews, the merging of Jenner’s children from the first two marriages with the four children from Kris’s first marriage—Kourtney, Kimberly, Khloé, and Robert junior—was a happy one. The eight of them performed together at the Jenners’ wedding as “the “Jennashians.” The Jenner children continued to live with their mothers, but they said that they frequently went over to their father’s house and that Kris embraced them. Then it all stopped.
The children maintain that Kris essentially turned on them. Kris said she and her husband stopped seeing the children “because you just got to a point where it became exhausting to be embattled all the time. We weren’t getting anywhere with constantly asking to see the kids and not getting a yes. And I think the kids really didn’t hear that side of it.”
Relations became further strained when Linda Thompson, after waiving child support at the time of divorce, took her ex-husband to court to get it. Jenner told me that the suit had a very negative impact on Kris’s willingness to integrate the families.
Jenner acknowledged that his focus was on Kendall and Kylie and his four stepchildren and that he thought, “I can hopefully build a relationship with the Jenner side once they’re old enough and mature enough and they’re out from under the apron of their mothers.”
Burt Jenner, who owns West LA Dogs, a day-care center for dogs, said he does not remember seeing his father more than twice a year for a period of roughly 10 years.
Brandon Jenner, who is 33 and in an accomplished indie-pop duo with his wife, Leah, still maintained a sporadic relationship with his father. But even he went through stretches of two to three years without ever hearing from him. The other two children also went through long periods of never seeing their father at all. Jenner said he was not invited to such milestone events as high-school graduations and would have gone had he known; the children and their mothers say he was invited and in some instances did not even respond.
When the Northridge earthquake hit the Los Angeles region, in 1994, Brandon, then 12, told his mother that his father had called to see if the family was O.K. His mother was delighted that Bruce had called. “Mom, I’m just kidding,” Brandon told her.
“I think the nail in the coffin for the relationship was the beginning of the TV show,” in 2007, said Burt. “There was a you-aren’t-part-of- this kind of thing. Kris made the choice to make a good TV show that was in their image and brand.” As she put it in a book she wrote called Kris Jenner … and All Things Kardashian, the title “Keeping Up with the Kardashians and the Jenners just didn’t have the same ring to it.”
Burt wonders now if it would have been better for him if his dad had not been an Olympic champion. “It’s very hard to have a father to idolize,” he told me. “It would have been much easier if he hadn’t won the Olympics.”
Burt is a formidable racecar driver, as his father was, winning the Octane Academy competition on NBC in 2013, which netted him ,000 in prize money and a car. “My father taught me on the athletic field,” Burt said. “The confidence in yourself to go out and win.”
But Burt, notable in the family for being bluntly candid, also said, “I was very fortunate to have an awesome stepfather to fill the void…. At the end of the day there’s no way I can get around it. I am ungodly thankful and I feel very fortunate to not have had my father in my life…. I learned how to open doors and shake hands and look people in the eye. Things that my dad never would have taught me.”
“There’s so much more to me than those 48 hours in the stadium, and I can’t talk about it,” Caitlyn says, thinking back. “It was frustrating.”
Photograph by Annie Leibovitz; Styled by Jessica Diehl.
Jenner does have regrets. “I have made a lot of mistakes raising the four Jenner kids. I had times not only dealing with my own issues but exes. [It was] very traumatic and there was a lot of turmoil in my life, and I wasn’t as close to my kids as I should have been.”
It was actually during one of the most difficult periods of his life, the attempted transition in the late 1980s, that they found a caring and loving father. As Cassandra put it, he was a better parent when he “was moving towards his authentic self.” As she said of her dad, “I would happily have traded a distant father for a loving, involved mom.”
Keeping Up with Bruce and Kris
Kris Jenner took over her husband’s foundering career after they were married. She got rid of Jenner’s handlers. She renewed his speaking engagements. He appeared in infomercials for Eagle Eyes Sunglasses and for a piece of workout equipment called the SuperStep and other products. They did an infomercial series called “Super Fit with Bruce and Kris Jenner.” The efforts were financially successful.
But after Keeping Up with the Kardashians started and became a runaway hit, the dynamics of the relationship changed, Jenner told me. “The first 15 years I felt she needed me more because I was the breadwinner…. Then really around the show, when that hit and she was running this whole show and getting credit for it and she had her own money, she didn’t need me as much from that standpoint. The relationship was different.
“I think in a lot of ways she became less tolerant of me. Then I’d get upset and the whole relationship kind of fizzled.”
One has to watch only a sampling of the show to see the interaction. “A lot of times she wasn’t very nice,” Jenner said. “People would see how I got mistreated. She controlled the money … all that kind of stuff.”
Kris Jenner acknowledged that her workload quadrupled as the result of the ever-expanding Keeping Up with the Kardashians empire and she “didn’t have the kind of time she had in the past.”
She also said Bruce was often angry and upset during the last years of the marriage. “He was married to me and he wasn’t who he wanted to be so he was miserable…. All I was doing was working very hard for my family so that we could all have a wonderful future, and he was pissed off.
“At the end of my relationship with Bruce he definitely had a lot of social anxiety,” Kris said. “That was one of the reasons we were in a struggle at the end. We fought a lot because we would go out together and before we got to the end of the block we were in a fight because he started saying, ‘When can we go home?’ ”
What strikes her now is how her husband, after fully embracing life for much of their marriage, “just decided I’m done now” without explaining his gender dysphoria until after they were divorced. “It was like the most passive-aggressive thing I think I’ve ever experienced.”
As she asked rhetorically of her former husband, “Why would you want to be married and have kids if this is what you wanted since you were a little boy? Why would you not explain this all to me?”
Jenner said that from his perspective the disintegration of the marriage had far less to do with gender issues and far more to do with the way Kris dealt with him: “Twenty percent was gender and 80 percent was the way I was treated.”
They separated in June 2013. He rented a house in Malibu. They were amicably divorced last September. The agreement was completed with no lawyers, an indication, Jenner said, “of 23 great years together.” He said that he retained the contracts that were his and she retained the ones considered hers. The agreement, filed in Los Angeles County Superior Court, states that they aimed to divide their assets evenly, but Kris almost certainly emerged much wealthier than Bruce, since she kept sole possession of all the business interests and intellectual property in her name—including Keeping Up with the Kardashians and its spin- offs.
Jenner knew that at some point he would have to tell his children of his gender identity. But any right to privacy he should have had was irrevocably lost in December of 2013 when he got a call from TMZ asking him if he had just had a medical consultation for the tracheal shave. Jenner remembers pulling his car to the side of the road. He pleaded that nothing be published because it would “destroy lives.” The pleas were unsuccessful. The item appeared online. Pacing the hallway of his rented home in Malibu that night after publication, he contemplated suicide with a gun he kept in the house. He decided not to go through with it. But he also realized that, with the story now out there, he was going to have to tell his children. He also knew he would now need a strategy for eventually going public with his transition. The TMZ disclosure had robbed him of any right to his own timeline.
He told each of his children individually, starting with Brandon, whose reaction was unequivocal: “I’ve never been more proud of you than I am at this moment.” The rest of the Jenner children reacted much the same way. They were already aware of their father’s identity as a woman. Their mother had told Burt and Cassandra roughly 20 years earlier, when they were 13 and 11. Brandon had assumed it because of the obvious physical changes. Brody was not told by his mother until he was 29. “As soon as I heard it, it was almost a relief. Because it just made a lot of sense growing up,” Brody told me. “Reasons and things like why he wasn’t there. Not around. I finally realized he had his own issues he was dealing with at that time.”
About a year ago, Brandon and Brody got a sobering glimpse of their father’s life when they went over to the Malibu rental house to surf. As they put on their wetsuits early in the morning, they saw that lights were on inside. Brandon went over to say hello, then quickly came back and told his brother they needed to leave immediately because he had just seen their father at the computer in a gown and earrings. Because they knew their father identified as a woman, they were not shocked. But they also knew he did not want them to see him dressed like this. “He wakes up at 4:30 in the morning probably because he’s not tired but [also] because that’s the [only] part of the day he actually gets to be” what he wants, said Brody. “That’s so sad, when you can’t be like that always.”
The Jenner children feel both happiness for their father and inspiration at his bravery. They also feel that their relationship with their dad will now have an opportunity to grow.
“I feel like he’s been the closest to us and the best parent when he’s been moving toward his true identity,” said Cassandra.
As part of the transition, Jenner started hosting intermittent and small gatherings called “girls’ nights,” casual occasions with wine and food in which Jenner could dress as desired and feel natural and comfortable in the presence of women. It was at a girls’ night that Cassandra met Caitlyn for the first time. “I was just nervous that I wouldn’t make her feel comfortable,” Cassandra said. “I was worried I wouldn’t say the right things or act the right way or seem relaxed.” But almost all of it melted away when she got there. “We talked more than we ever have. We could just be girls together.”
It’s Her World Now
For the Jenner children the issue of the transition has become a non-issue. They all still see their dad as their dad regardless of any gender label. Brandon said he was a little taken aback when he saw Caitlyn for the first time after surgery and she pulled her top up to reveal her new breasts. “Whoa, I’m still your son,” he gently reminded her. But the moment easily passed. After so many years of non-contact and hurt, one of the most stirring parts of the transition has been the renewal of the relationship of the Jenner children with their father.
Except that disagreement over the upcoming E! docu-series has posed yet another hurdle. The children believe that with the right producers the show could be wonderful on multiple levels, including elevating public consciousness of the issues surrounding the transgender community, much the way the Sawyer interview did.
The docu-series will be produced by Bunim/Murray, the company responsible for such shows as The Real World, The Simple Life, Bad Girls Club, and, of course, Keeping Up with the Kardashians. Bunim/Murray is credited with inventing reality television: nobody does it better. But this is not your typical reality show. Their father’s adamant decision to use some of the same producers and much of the same crew who have produced the Kardashian episodes for 10 seasons only enhanced their concern that the show would devolve into maximum mayhem and minimum social awareness. The children said they were interested not in their own financial gain but in ensuring the legacy of their father as perhaps the most socially influential athlete since Muhammad Ali.
At a meeting at the Jenner house with another prospective producer, who was not chosen, Brandon laid out his concerns succinctly: “You go on E!’s Web site, the Bunim/Murray Web site, and you look at all the shows, every one of them is a circus.”
“With Bunim/Murray and E! it’s been the opposite of inspiration,” he said during the meeting. “Oh my God, we’re diving into the lion’s den—they’re gonna make a show about the Jenners versus the Kardashians.”
Brandon Jenner wants his father to know this is simply the kind of disagreement that happens in families. He wants his dad to know he loves and admires her, as do all the Jenner children, just as he hopes that his father’s love will not become conditional, as it has been in the past.
“This is the fourth quarter of [her] life. But within our relationship this is the first quarter, the relationship that [she] has with the kids. Regardless of the show and all that stuff, there will be a fourth quarter of the relationship. And I envision the fourth quarter as having a 15- or 16-year-old daughter who knows her grandparent as ‘Mapa’ or whatever Dad wants to be, and loves that grandparent for who she is.”
E!’s head of programming, Jeff Olde, hopes the children will decide to participate once they see the quality and tone of the show. He respects their decision and knows it is “coming from a place of pure love.” He also said this will be a quality show with a totally different feel from other E! offerings. “It’s not at all a Kardashian spin-off…. We will not resort to spectacle. That doesn’t mean we can’t have fun with it.”
“We all love ratings,” Olde said, “but we understand the power and responsibility to be able to share this story.” Olde, who is gay and married, said he and his husband have been in the trenches for almost 20 years fighting for equal rights. “This is so far beyond television, on a personal level. If I get one thing right in my professional career, it will be this.”
Jeff Jenkins, the executive vice president of development and programming for Bunim/Murray, echoed Olde’s sentiment and said that “ratings are not the goal” of the series. “It is to tell Bruce’s story the way he wants it to be told.” Bunim/Murray has produced several well-received shows on members of the L.G.B.T. community, including Pedro Zamora, whose groundbreaking participation in 1994’s The Real World: San Francisco made him one of the first openly gay H.I.V.-positive people to be depicted on prime-time television.
There are many out there who think the E! series, while slightly more elegant perhaps, is just a stunt to make money. Caitlyn Jenner is prepared for the criticism just as she is also prepared with an answer.
“ ‘Oh, she’s doing a stupid reality show. She’s doing it for the money. She’s doing this, she’s doing that.’ I’m not doing it for money. I’m doing it to help my soul and help other people. If I can make a dollar, I certainly am not stupid. [I have] house payments and all that kind of stuff. I will never make an excuse for something like that. Yeah, this is a business.
“You don’t go out and change your gender for a television show. O.K., it ain’t happening. I don’t care who you are. It ain’t happening, O.K.? You don’t do it.”
Caitlyn’s 89-year-old mother, Esther, while enormously proud of her son’s courage, is among those who have wondered about motive. “I woke up one night and all I was thinking about is: Why is it necessary [for Caitlyn] to go through all these surgeries?” Esther said. “Is this all about making money? And that was bothering me. He’s lived a life the last 25 years—and I don’t know if it was both he and Kris or mainly Kris—it seemed like their lifestyle was about money; that’s why it came to my mind.”
The lifestyle was the materialistic equivalent of morbid obesity, but Jenner never was a part of it. I can say unequivocally that he actually hates to spend money. The recently purchased house did cost .6 million, but that is low by celebrity standards, and it has a mortgage on it. The big-ticket items, a 2011 Porsche 911 GT3 RS that cost somewhere around 0,000 and the country-club membership, were birthday gifts from Kris. I watched with fascination as he fetched golf balls out of the water hazard on the sixth hole at Sherwood with a pole so he would never have to buy any himself, honorably returning the ones stamped with “99” to fellow club member Wayne Gretzky.
The Legend Becomes Her
It was early May, and Caitlyn had just gotten three letters from transgender women thanking her for the interview and the dignified way in which ABC and Sawyer had handled it. One of them was addressed “Bruce Jenner, Malibu, California,” as if she had become her own country. An incredible 16.9 million had watched on a Friday night.
“Honestly, since the Diane Sawyer piece every day it’s exciting to go to the mailbox, because I get letters every day from all of these people from all over the world,” she told me. “I’ve gotten a lot from trans women, telling their story, and how excited they were to see the Diane piece.”
She first watched the Sawyer interview on ABC’s East Coast feed with the Kardashian klan, sitting between Kendall and Kylie. The two youngest children worried that the reaction would be negative, only to be put at ease by the Twitter messages rolling in from famous people—Lady Gaga and Miley Cyrus and Oprah Winfrey and Jimmy Fallon and a dozen others. Caitlyn then watched a second time at nine P.M. with the four Jenner children and their mothers. Brandon called the experience “one of the best nights of my life.”
“Was it tough to watch? Of course it was,” Caitlyn told me. “I never thought in a million years I would ever have to divulge such private, intimate feelings I’ve had all my life…. I was also excited to get it off my chest. Scared but excited.”
The reaction from the celebrity community was overwhelmingly positive, perhaps because Caitlyn Jenner is a fellow club member. The estimated 700,000 transgender women and men in the country are virtually all anonymous, too many of them suffering from job discrimination and violence. A 2013 report co-authored by a variety of equality and human-rights groups, including the Human Rights Campaign, said that transgender workers have a 14 percent rate of unemployment, double that of the general population; 44 percent are under-employed; and 15 percent have a household income under ,000, as opposed to 4 percent in the general population. The National Transgender Discrimination Survey Report in 2010, based on roughly 6,500 responses to an extensive questionnaire, determined that the attempted-suicide rate for transgender women and men was a staggering 41 percent, compared to 1.6 percent in the general population.
I can report that Caitlyn seems immensely happy, relaxed, with a shiny sense of purpose and confidence. She can’t wait when she goes out now to tell the paparazzi to “make sure it’s a good shot,” instead of asking patrons to help shield her from them in the parking lot of the local Starbucks. She looks forward to re-creating the atmosphere of “girls’ night” on a more regular basis, “where everybody is treating you the same way. You can talk about anything you want to talk about. You can talk about outfits. You can talk about hair and makeup, anything you want. It becomes not a big deal.”
She is aware of the appalling conditions in which many transgender women and men live, and said that in her E! show she will focus on ways of lowering the rates of suicide and attempted suicide, among other issues. Caitlyn also plans a segment in which she sees if she can still hit a golf ball 300 yards off the tee, even with those very ample breasts. There is a road trip planned, in which Caitlyn and several transgender women will take an R.V. from the Los Angeles area to San Francisco to visit a center for transgender youth, and then on to Napa Valley.
She said she now accepts the children’s decision regarding the E! series. “I think it’s better for the show right now. It keeps me on point and doesn’t distract with all the family issues.”
As a possible peace offering, Caitlyn went over to Brandon and Leah’s house recently, not to make one last charge to persuade but to help plant a garden. “I think the relationship will take a new shape,” said Brandon. “My hopes that the relationship would blossom, that we would turn over a new leaf, has kind of turned into, I just want a relationship that is sustainable. I just want to have the best parts as possible.”
On July 15, Caitlyn’s first major public appearance, she will be awarded the Arthur Ashe Courage Award at ESPN’s ESPYs in Los Angeles. Its past winners include Muhammad Ali, Nelson Mandela, and Billie Jean King. All 10 of her children and stepchildren are expected to be onstage when she accepts it.
A Different Kind of Gold
I last saw Caitlyn on May 6. It was the end of an emotional photo shoot with Annie Leibovitz for Vanity Fair in which, at one point, Leibovitz teared up. “I felt like I saw the making of Caitlyn,” she said. She was right. Positioned lengthwise on the couch, she had the look of an elegant starlet with only a cigarette holder and dark oval-shaped glasses missing. Mixed in was a pinch of Gloria Swanson in Sunset Boulevard, as if it were Caitlyn making love to the camera and mouthing the words “All right, Ms. Leibovitz, I’m ready for my close-up.” The fear that she would not be comfortable with herself had already evaporated. Which also meant that the comfort of others with her was effortless.
The house was filled with production assistants and makeup and wardrobe people for the shoot, giving it vitality that just a few weeks earlier seemed impossible. She really should move. She doesn’t have to be alone on the mountaintop anymore.
After the last picture was taken, Jenner thanked all those who were there. She had been primped and pampered to look gorgeous, and the reaction had been equally gratifying. The gold medal for winning the decathlon, which Caitlyn had left in the safe in the home in Hidden Hills where she and Kris had lived, had finally been retrieved. It was on the table in front of her. “That was a good day,” she said as she touched the medal. Then her eyes rimmed red and her voice grew soft. “But the last couple of days were better.”
Cassandra was there. As she heard Caitlyn speak, she saw a vulnerability and authenticity she had never experienced before. She went to the couch and sat next to Caitlyn. The moments of the past were still there, there was no way of knowing the moments of the future, but in the space of that single moment was all you could possibly hope for, a daughter with her dad, a dad with her daughter.
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