CHAPTER FIFTEEN 

In early 2010, I found myself in Los Angeles working on a documentary about Michael Jackson. On Valentine’s Day, I happened to be sharing a romantic dinner with my girlfriend at Mastro’s steakhouse in Beverly Hills. Midway through the meal, my date nudged me and pointed out that Kris Jenner was dining a few tables down. I had barely kept up with the Kardashians and was only vaguely familiar at the time with Kris but, as an avid sports fan, I was acutely aware of whom she was married to. I found it odd, then, that on Valentine’s Day, she wasn’t with Bruce Jenner, but rather a female companion.

After dinner, as we were waiting for the valet to bring the car, Kris stepped out with her friend, a middle-aged woman whom I didn’t recognize. She was immediately ambushed by a cameraman from TMZ. “Where’s Bruce?” he shouted. “He’s golfing,” Kris replied. I thought nothing more about the incident until 2012, when the first bizarre reports began to surface. In January of that year, Robert’s widow, Ellen, claimed that Bruce’s first wife, Chrystie Crownover, had confided to her over drinks one day that Bruce had a penchant for cross-dressing.

“Of course Bruce was every woman’s heartthrob when he was that age, right?” Ellen claimed that she asked Chrystie about their marriage. The answer surprised her. “Yeah, until I went on a trip and I came back and he had gone through all my clothes. And I found my bras. . . . He’d clip them together and wear them. I couldn’t live with that.”

Crownover denied the bizarre report at the time, and most people assumed it was simply more tabloid trash. A year later, stories surfaced that Bruce had moved out of the family’s home in June 2013 and was living in Malibu. By then, his face was beginning to take on a decidedly feminine appearance, but most assumed that his unusual facial features were merely the result of one of the numerous plastic surgeries that Bruce was fond of. The whole family, in fact, were fans of surgical enhancement. A friend of Kris’s once told me that “the Kardashians live by the knife.” Kris, in fact, had gone through a televised facelift on a 2011 episode of Keeping Up with the Kardashians so that she could look good for Kim’s wedding to Kris Humphries and had bragged about undergoing at least two boob jobs.

The family’s former nanny Pam Behan later recalled that Bruce had once suggested that she have a procedure done, even though she was only a teenager. “Bruce told me one time that I was a cross between Farrah Fawcett and Goldie Hawn, which put a big smile on my face,” she wrote. “Despite this, the subject of plastic surgery came up one day in an unexpected way. Bruce was looking at me funny,” she wrote. “ ‘What?’ I asked as he stared at my face. ‘You should probably have a little taken off your nose.’ Huh? I’m nineteen. It had never, ever occurred to me that I might need a nose job. . . . I guess in the land of the beautiful and perfect people, there was always some ‘work’ that could be done.” Indeed, Bruce had talked often about undergoing a botched facelift and nose job in the mid-’80s, which he claimed had effected his self-esteem. He later underwent another procedure to correct the first one, which was featured on an episode of Keeping Up with the Kardashians.

“If you Google my name, ‘the worst plastic surgeries of all time’ or whatever it is . . . they’ve compared me to Michael Jackson,” he said on the show. So his changing facial features weren’t necessarily indicative of anything unusual.

By the fall, the reports of a separation had gained traction and were already an open secret. Finally, on October 8, the couple made it official. “We are living separately and we are much happier this way,” they said in a joint statement issued to E! News. “But we will always have much love and respect for each other. Even though we are separated, we will always remain best friends and, as always, our family will remain our number one priority.”

Bruce could barely disguise his jubilation at a Virginia speedway event that weekend when he announced, “I’m finally free to do what I want and live life the way I want.” For her part, Kris delivered what appeared to be a low blow when she told New You magazine, “The one regret, if I had to do it over, would be divorcing Robert Kardashian.”

Before long, the newly single sixty-three-year-old Jenner had grown his hair out into a ponytail, and was spotted sporting earrings and lip gloss. The long-dormant rumors started anew, especially after he was seen leaving the office of a Beverly Hills plastic surgeon. He confirmed that he was planning to undergo a “tracheal shave,” which in effect removes the Adam’s apple and is a common procedure among transgender women before they undergo gender-reassignment surgery, better known as a sex-change operation.

At the time, however, Bruce denied he was transitioning. “I just never liked my trachea,” he claimed. The transgender community wasn’t buying it. Dr. Marci Bowers, the first transsexual woman to perform gender reassignment surgery on others, told Radar, “The real hallmark of being male is the presence of an Adam’s apple. Someone choosing to have that reduced is pretty much making a statement that when they’re going to be dressed as a woman, they’re hoping to pass as a female in public. . . . That could be the step that Bruce is making. It’s complicated, but it would be very surprising if it was just a final step for doing something about a feature he didn’t like, and not the beginning of a slippery slope [to gender reassignment surgery].”

In January 2014, he was photographed leaving the same clinic, the Beverly Hills Surgical Center, with a bandaged throat, having undergone the procedure. The news only escalated the rumors. A month later, TMZ asked Kris about the reports and whether she would support Bruce if he was indeed transitioning. Laughing, she merely said, “You’re crazy,” before ducking into her car. Soon afterward, she told the Daily Mail that “99 per cent of the rumors are made up.” While promoting her cookbook a few months later, she was once again asked about the rumors. “It’s silly! [The tabloids have] been saying that since the ’70s, so you think he’d be cooked by now. . . . They just keep regurgitating the same old stuff.”

In December, Chrystie Crownover had denied that Bruce was a cross-dresser when she was married to him, as Ellen had alleged the previous year. She believed she knew who had been spreading the rumors. “This is a plan by Kris to destroy his life, she’s not a pleasant woman. . . . She’s out to get him. She doesn’t want him to be happy,” Chrystie said. “There was no suggestion of cross-dressing when I was with him. He’s a man’s man.”

But the idea that Kris was behind the reports was clearly preposterous. As we would soon learn, Bruce’s ex-wife had no interest in exposing his secret. On the contrary, Kris Jenner was getting nervous.

In 1975, a tennis player and opthamologist named Richard Raskind underwent gender-reassignment surgery and emerged as a woman under her new name, Renée Richards. Raskind had served as a doctor in the United States Navy where he played tennis for the Navy Team and won both the singles and doubles all-Navy championships, thanks to a ferocious serve that regularly stymied opponents. By 1974, he was ranked thirteenth in the nation in the men’s thirty-five-and-over tennis standings.

A year after her sex change, Richards applied to play in the US Women’s Open but was denied the opportunity after she refused to take the sex-verification chromosome test required of all women competitors. A year later, seeking to enter the US Open once again, she filed an injunction under New York State human rights law and the Fourteenth Amendment of the Constitution to prohibit the US Tennis Association from subjecting her to the sex-verification test. The judge determined that the test was initially designed to “prevent fraud”—specifically to weed out men masquerading as women, which was not the case with Richards. The judge ruled that USTA had employed the test specifically to prevent her from competing in the tournament, knowing she would have failed it. “This person is now a female,” the judge ruled. Requiring her to take the test was “grossly unfair, discriminatory and inequitable, and a violation of her rights.”

At the time, she was widely mocked for her efforts, with Sports Illustrated describing her as an “extraordinary spectacle.” But with the court victory, she was free to play professional tennis. In her very first US Open, in 1977, she reached the doubles finals, losing a close match to Martina Navratilova and Betty Stöve. Two years later, she won the US Open singles title in the thirty-five-and-over category.

Around the time that Richards emerged as a pioneer for transsexual rights, Bruce Jenner was emerging as the world’s greatest athlete at the Montreal Olympics. He would later reveal that he was watching her battle closely at the time and that Richards would serve as his “inspiration.”

When I was attending university in Montreal during the eighties, I organized a human-rights lecture series. One of the speakers happened to be Harry Edwards, who in 1968 had organized the Olympic Project for Human Rights, in which two black athletes, Tommie Smith and John Carlos, had given the black power salute, fists raised, on the podium at the Mexico City Olympics. In the years since, he had emerged as an influential sports sociologist who focused primarily on race relations in sports. When I picked up Edwards at the airport, he told me he had just come from mediating a crisis at a Los Angeles university that I believe was UCLA. It seemed that the US Olympic track team had been using the university facilities to train but that the athletes were in open revolt because they were refusing to use the same locker room as the US team’s star athlete, Carl Lewis. The mostly black athletes, Edwards told me, believed that Lewis was gay and therefore wanted nothing to do with him. He had been called in to try to resolve the conflict.

A few years earlier, Jenner’s successor as Olympic decathlon champion, Britain’s Daley Thompson, had sported a T-shirt during an ABC news interview bearing the words, “The world’s second greatest athlete is gay.” It was an obvious reference to Lewis. The winner of the Olympic 100 meters is informally dubbed the “world’s second greatest athlete,” with the decathlon winner considered the greatest.

It is a reminder that track and field—a sport dominated by black athletes who hold deeply religious views—is rife with homophobia, and we can assume that a transgender athlete would have been welcomed with no less hostility than Lewis had been. And yet it’s still unclear whether Jenner was struggling with his gender identity at the time he started out in track and field or whether in fact the process started later, perhaps even as a result of his athletic training.

The question first arose when Bruce’s former Olympic teammate Ken Patera gave an interview claiming that Bruce had used anabolic steroids in his training regimen before they were banned. After a mediocre showing in the 1972 Munich Olympics, Jenner had turned to Patera—the reigning Pan Am Games champion—for help in strength training. Both used steroids legally to pump themselves up, he claims, until they were added to the banned-substances lists by the International Olympic Committee in 1975.

Patera believes the chemicals could have played a role in Jenner’s eventual transition. “Maybe that flipped a switch in his brain,” he said in May 2015.

Although the claim seems far-fetched, it is not entirely without precedent. Heidi Krieger was a world-champion East German shot putter who had taken massive doses of steroids since she was sixteen as part of the notorious East German doping program. In 1997, she underwent gender-reassignment surgery to become a man and became known as Andreas Krieger. He later claimed that the androgenic effects of steroids altered his body chemistry and exacerbated his existing gender dysphoria, contributing to his gender transition.

It is an intriguing theory, but when Bruce Jenner finally decided to end all speculation and go public with his transition in the spring of 2015, he revealed that he had been struggling with gender-identity issues long before his athletic career took off, and that he secretly wore dresses as a young boy growing up in Tarrytown, New York.

The interview—broadcast by ABC’s Diane Sawyer during a two-hour 20/20 special—was teased in advance by the network with a number of provocative quotes from the pretaped interview. “My whole life has been getting me ready for this. . . . My family members are the only ones I’m concerned with. . . . It’s going to be an emotional roller coaster but somehow I’m going to get through it. . . . It made me who I am. . . . I want to know how this story ends. How does my story end?”

But until viewers heard Sawyer ask him the question on the April 24 broadcast, few people knew for sure. “Are you a woman?” Sawyer asks the sixty-five-year-old former Olympian early in the interview. “I’ve always been very confused with my gender identity. For all intents and purposes, I am a woman,” Jenner replies.

The show achieved its highest Friday-night ratings in more than fifteen years, as almost 17 million viewers tuned in to hear Jenner’s dramatic revelation. There was no shortage of intriguing details during the two-hour special. He revealed that he had been struggling with his gender identity for decades and had even contemplated suicide after his Adam’s apple–removal surgery was made public. “I thought, wouldn’t the easiest thing to do right now—and I could see where people get to that—is go in the room, get a gun, boom? Pain’s over, it’s done, go to a better place. And I thought, nah. I can’t do something like that. I mean, I want to know how this story ends.”

He disclosed that his first wife, Chrystie Crownover, was the first person he had told about his cross-dressing, despite her recent denials. Three days later on Good Morning America, Chrystie confirmed that he had indeed shared his feelings early on in their marriage, telling her “he wished to be a woman.”

She recalled, “It was this type of shock in my experience, but he opened up his heart and revealed it. [He said] he had to share with you this dark secret that is strong, and he told me he always desired to be a female and, understandably, I was speechless. I didn’t actually know what to say.”

More surprisingly, Jenner revealed to Sawyer that he had actually started to transition in the ’80s, before he met Kris. “I had been on hormones for five years and I was a really solid 36B-something and you really can’t hide those things,” he laughed. “And [Kris] goes, ‘Well, okay, you like to wear women’s clothes.’ And I kind of downplayed it some. I feel in a lot of ways that when you love somebody you don’t want to hurt them.”

At one point, Sawyer asks him whether he’s sorry he participated on Keeping Up with the Kardashians. He provides a revealing answer, appearing to confirm years of accusations that the reality show bears no resemblance to reality. “I had the story,” he says. “We’ve done four hundred twenty-five episodes, I think, over almost eight years now, and the entire run, I kept thinking to myself, ‘Oh my God. This whole thing, the one real, true story in the family was the one I was hiding, and nobody knew about it.’ ”

Asked about his relationship with Kris, he seems to imply that she was less than supportive. “It was tough on her. I understand that. Kris is a good woman, I’ve got no complaints with her. She’s a good person. Honestly, if she would’ve been really good with it, and understanding, we’d probably still be together.”

He then reveals an unexpected detail about their time together, especially after months of denials by Kris. He claims that during their relationship, she had actually seen him dressed in women’s clothing. “She didn’t say much,” he recalled. “Just, like, ‘Okay, you gonna change now?’ I probably was not as good at saying that this was down deep in my soul and ‘I don’t know if I can go any farther like this.’ ”

By the next day, the reverberations of the interview were being felt around the world, but nowhere more so than in the Kardashian family, where Bruce’s revelations were already wreaking havoc. The first controversy erupted when the media descended on Kris for comment and wondered why she had not participated in the special, even though Jenner’s other two wives, Chrystie Crownover and Linda Thompson, had provided supportive comments. At the end of the broadcast, Sawyer claimed that Kris had declined to comment. That prompted blogger Perez Hilton to report on her refusal, at which point Kris Tweeted, “@PerezHilton fuck you Perez no one asked me to comment. . . . and I’m sitting with Bruce now watching this show so let’s keep it real.”

But the network was quick to set the record straight. “ABC News sent an email to her publicity team more than once,” they said in a statement. “They called and said no comment.”

Finally, Kris backtracked slightly on her previous claim. “Kris does not have official representation but a message was left at her office and she was asked for fact checking. Kris said she was unable to respond because she had not seen the special. She did not say, ‘No comment,’ ” her publicist told People.

In the days leading up to the special, reports were circulating that Kris was petrified about what Bruce might disclose. Two days before her ex-husband was scheduled to sit down with Sawyer, it was alleged that she had dispatched one of her daughters to remind him he has a financial stake in the empire they created and not to say anything to jeopardize it. In April, the New York Daily News reported that Kris “is so nervous about the tell-all that she tried to talk the former Olympian out of doing it.”

Of course, true to form, no matter what reservations she had about her ex-husband’s transition, Kris was not about to pass up an opportunity to cash in on the publicity. At least that’s how cynics interpreted the two-part Keeping Up with the Kardashians special, “About Bruce,” which aired in May. In it, Bruce discusses his transition with his family, revealing the truth for the first time.

A year earlier, the transgender surgeon, Dr. Marci Bowers, had predicted that if Bruce did decide to transition into a woman, the process could be harder on his family than on him. “It’s very cathartic and liberating to go through, but it’s much more difficult for the people around you,” she said at the time. “His family’s going to feel all sorts of reactions: shame, betrayal. They’re going to end up discussing it and he’s going to need to be patient with that.”

Sure enough, in the special, we see the reactions of each member of the family, except for Rob, who was still lying low. Surprisingly, the usually confident Khloé—who had brought along as a present a stack of size-13 high-heeled shoes—appears to be the most nervous before he arrives. She tells her siblings, “I don’t know if I’m saying the right thing, if I’m using the right terminology. I don’t want to offend anyone. I’m fine with him dressing as a woman. I want Bruce to be happy.” But when they get together, she accuses him of lying to them. “I didn’t lie to you, Khloé, I just didn’t tell you,” he responds. She demands to know when he plans to actually transition into a woman, telling him he owes it to them to reveal the truth.

“Are you planning on not being Bruce anytime soon?” she asks. When he confirms that’s the plan, she fires back, “You have children! You don’t have to answer to us, but you need to tell us! I don’t care that you want to do it, I support you, I have always supported you, but I don’t think it’s fair that you won’t tell us how close this is in the near future. We’re still your kids!”

It is clear that the most accepting sibling is Kim, who not only offers her full support but offers to help Bruce with his new female wardrobe. “Girl, you gotta rock it and you gotta look good. If you’re doing this thing, I’m helping you,” she tells him. At one point, she asks the question that is on everybody’s mind. “Are you going to fully become a woman?”

“I see myself in the future that way,” he says.

When Diane Sawyer had asked him about his sexual orientation, Bruce had been adamant. “No! I am not gay! I am not gay. I am—as far as I know—I am heterosexual. I’ve never been with a guy. Sexuality is who you’re personally attracted to, who turns you on, male or female. But gender identity has to do with who you are as a person, and your soul, and who you identify with inside.”

When he tells Kim that he is still attracted to women, but considered himself to be “totally heterosexual,” she called him on the glaring contradiction. “If you’re a woman, then aren’t you a lesbian?” Rather than address the question head on, he offers a vague reply. Many wondered whether his Republican leanings and long-held religious beliefs prevented him from acknowledging Kim’s logical conclusion.

But despite the fact that she appeared to be asking uncomfortable questions, Bruce has long maintained that Kim has been the most supportive of his transition. “Kimberly has been by far the most accepting and the easiest to talk to about it,” he told Sawyer. It’s hardly surprising, considering her long history of opposing homophobic bigotry. As far back as 2009, Kim issued a strong statement when the California Supreme Court upheld the homophobic referendum, Proposition 8, in which Californians had voted to ban gay marriage in their state. In response to the regressive decision, Kim wrote on her blog, “This really makes me sad. I thought we were more forward thinking than this, and I’m disappointed in the Supreme Court for being so closed minded. Everyone . . . gay, straight, bisexual, transgendered, EVERYONE should have equal rights to marry who they want to.”

She had also been a strong supporter of Barack Obama as well as the Occupy Wall Street movement, in contrast to both her mother and stepfather, whose own political views were far less enlightened. “My household is really split up,” she told a red-carpet interviewer in 2009. “The parents are Republicans and the children are Democrats. So it’s like a political warfare in our household when we talk about politics.” Indeed, Kris once told a reporter that she and Bruce were “complete Republicans” and that every TV in their house was tuned to Fox News. Kim would later credit Kanye with helping her accept and support Bruce’s transition—a marked contrast to the numerous rappers who reacted with homophobic disdain after the news surfaced. Snoop Dogg referred to Caitlyn Jenner as a “science project,” while Timbaland Tweeted, “His Momma Named Him Bruce, I’mma Call Him Bruce.”

In the end, all the children end up offering their support to Bruce in his transition, despite any initial misgivings or apprehension about meeting “her” for the first time. The Huffington Post, like many media, would shift from its usual disdain for all things Kardashian to an appreciation for the family’s role in helping shift society’s values on an important social issue.

“Yes, it would have been a big deal for a former Olympian to come out as transgender no matter what, but couple that with Caitlyn Jenner doing it on the heels of a very public divorce in a family that documents every waking moment of their lives, and it’s a whole new ballgame,” the site observed. “The support of each of her family members has gone a long way to showing the public exactly how to react to this kind of change.” Suddenly, the family were no longer responsible for the decline of Western civilization but rather a force for good. Who would have thunk it?

The emotional high point of the “About Bruce” special is undeniably Bruce’s on-air reunion with Kris. Publicly, Kris had professed to support her ex, Tweeting, “Not only was I able to call him my husband for 25 years and father of my children, I am now able to call him my hero.” Privately, reports were swirling that she was feeling humiliated and deeply resentful. In the episode, the estranged spouses have clearly not spoken in a long time and Kris is reeling at the recent string of revelations about his new life, even though the Keeping Up with the Kardashians special was allegedly filmed before he went public to Diane Sawyer. When the two sit down together, Kris appears distraught, breaking down in seemingly genuine tears. It is clear that she hasn’t been using the “tear stick” that her daughter is said to employ on occasion when she wants to display emotion on the show. Bruce tells Kris he doesn’t want to hurt the family, especially her. “We’ve raised amazing children and those memories will live inside forever,” he says.

“Being honest is something we all would have appreciated,” Kris tells him. “The truth in your head is different than your actions. I always knew that you struggled with wanting to dress differently and that was something you did when you got that urge. I don’t know when you went from, ‘This isn’t working for me anymore and I’m going to start taking hormones.’ You never told me you were taking hormones. . . . You never said this was going to be the end result, ever.” After she accuses him of being dishonest, Bruce refuses to be put on the defensive. “You know you treated me badly those last four or five years of our marriage.”

During their encounter, Kris admits that she knew he had been taking hormones before he met her but denied knowing he wanted to be a woman. She concludes by telling him, “I miss Bruce and it’s going to take me a minute to mourn that relationship. You think you’re going to grow old with someone. . . . I have to mourn Bruce Jenner because I miss Bruce, I’ll never be able to have Bruce, and all I have are my memories. I feel like Bruce died, and it’s really hard for me to wrap my head around that.”

On February 7, 2015, Bruce was driving a Cadillac Escalade when he rear-ended a Lexus, pushing it into oncoming traffic where it crashed head-on with a Hummer, killing the Lexus’s driver, sixty-nine-year-old Kim Howe.

The question Jenner dodged for months was whether or not he would be charged with reckless driving. In August 2015, there were reports, quickly denied by the LA County Sheriff’s Department, that the department would recommend that Jenner be charged with vehicular manslaughter, which carries a potential sentence of up to one year in jail.

Then, on September 30, 2015, the Los Angeles district attorney decided against charging Caitlyn.

“We believed from the start that a thorough and objective investigation would clear Caitlyn of any criminal wrongdoing,” Jenner’s attorney Blair Berk said in a statement. “We are heartened the District Attorney has agreed that even a misdemeanor charge would be inappropriate. A traffic accident, however devastating and heartbreaking when a life is lost, is not necessarily a criminal matter.”

Although she was acquitted, Caitlyn was facing multiple multimillion-dollar lawsuits for negligence by victims, and their family members, of the deadly crash. Jessica Steindorff, a twenty-nine-year-old woman who was driving a Prius involved in the crash, sued Caitlyn in June 2015 for property damage and personal injury, and Kim Howe’s stepchildren hit the transgender reality star with a wrongful death lawsuit.

A longtime friend of Jenner’s accused him of misdirecting the serious offense by promoting his transition.

“Before Bruce got into the accident, he gave the world hints about his true sexuality,” the friend who only agreed to be referred to as “Dan” said. “After the accident, he went full steam ahead. I truly believe he was trying to misdirect the negative publicity he received after the car crash. I don’t think he would have gone so fast if he hadn’t been in an accident. And it was clear he was worried about being charged in some way related to the death of the elderly woman. The Diane Sawyer interview was a great way to derail the whole thing and to turn the attention to his transgender. To this day I remain skeptical about Bruce’s true motives.”

By the time the special aired, Bruce had still not officially come out as a woman. He had told Sawyer, in fact, that he still wanted to be referred to as “he.” It was around this time that I was put in contact with an NCAA coach who had known Jenner for years. He told me that he had been in contact with his old friend since the separation and that Bruce had confided what finally led to his decision to go public.

“I couldn’t be part of the Kardashian circus anymore,” he said. “I have to be real.” It’s similar to the language that he used on the Diane Sawyer special when he said, “This whole thing, the one real, true story in the family was the one I was hiding, and nobody knew about it.”

The coach also told me that Bruce had revealed that Kris had influenced him to suppress his desire to be a woman for all those years. “She told him he should pray,” he reveals, “that church would help heal him.”

This sounded to me suspiciously like conversion therapy, though I’m not entirely sure whether the word heal was used by Kris or by the coach. Still, the idea of using religion to suppress homosexuality has a troubling history associated with evangelical Christianity, especially during the ’80s and ’90s, when the idea gained momentum in various Christian ministries throughout the United States. In a 2015 article about the practice, the Atlantic Monthly cites the example of a girl named Julie Rodgers to illustrate how such therapy typically works.

“After she came out as a lesbian in high school, [Rogers’s] conservative Christian parents urged her to join a ministry in Texas to help make her straight. Ministry leaders promised her that if she continued praying, reading the Bible, attending meetings, and of course, refusing to identify as gay, her sexual orientation would eventually change and she could even marry a man.”

Evangelical Christians were fond of citing the supposed successes in which homosexuals underwent conversion or “reparative” therapy and thereafter labeled themselves “ex-gays.” Kris Jenner was of course an early adherent of evangelical Christianity and attended prayer sessions led by Pat Boone, who has been regularly accused of homophobia. In the 2008 Kentucky election, for example, he recorded a robocall for Senator Ernie Fletcher, who was facing a tough Democratic opponent:

“Now, as an American and a Christian I am very conservative about the upcoming governor’s election,” Boone said on the calls. “Ernie Fletcher is a typical Kentuckian; he’s worked long and hard for the state, its people, and its traditions. And, of course, he has come under attack by political opponents and now he faces a man who wants his job, who has consistently supported every homosexual cause: same-sex marriage, gay adoption, special rights to gay, lesbian, bisexual, even transgender individuals.”

Before she founded her own church, Kris was a regular attendee of the Calvary Community Church in Westlake, California. The church has long been associated with homophobic positions. As recently as 2012, the church leadership fired a member of Calvary’s executive team, Kevin McCloskey, when he came out as gay. He later wrote an essay for the Advocate about what happened when he revealed that he was dating a man.

“They were shocked to learn about my sexual orientation and were genuinely concerned for my family and me and all we were going through,” he wrote. “ ‘Even if I wanted to keep you,’ my senior pastor said, ‘you know it would never be accepted by the congregation.’ I knew he was right. Our church is located in a very conservative, family-oriented enclave of Southern California, with very few openly gay people.”

When Kris Jenner sought a pastor to run her new church, she chose a former pastor from that same church, Pastor Brad Johnson. Before he served at Calvary, Johnson received his training under another evangelical minister, Rick Warren, when Johnson served as a teaching pastor at Saddleback Church in Orange County.

Warren came under fire when he gave the invocation at President Obama’s 2009 inauguration, and it was later revealed that he had posted a YouTube video supporting California’s Proposition 8, the referendum to outlaw gay marriage in that state. More controversially, he was said to have been an early supporter of Uganda’s infamous bill to make homosexuality a capital crime, and in March 2008, he was reported to have traveled to the country and told the Ugandan Church that gay rights is “not a civil rights issue,” because homosexuality is not to be tolerated. “We shall not tolerate this aspect at all,” he allegedly said. While he would maintain that he never supported the Ugandan bill and would call it “un-Christian,” his earlier statements gave a fairly good idea of his views on homosexuality.

Apart from her religious affiliations with a virulently homophobic church, there is no evidence of Kris Jenner herself ever taking a stand on gay rights. A woman who knew her and Bruce for more than twenty years recently told me that she doubts Kris is homophobic.

It’s not so much a question of Kris having a problem with gay people. She knows plenty. But you have to understand the circles that she and Bruce traveled in. Neither of them, let’s face it, are very sophisticated. She was never comfortable with the liberal, secular Hollywood crowd. She had lots of opportunities to hobnob with those people but she preferred the Giffords [talk show host Kathie Lee and her late broadcaster husband Frank] and the Garveys. Quite conservative, not very well educated. She and Bruce were Republicans but not the right-wing, fire-breathing, bigot variety. This was California, after all. So I think she just didn’t really understand it, even if she really knew that Bruce had those tendencies way back when. She couldn’t wrap her head around that kind of thing. Gay people, maybe, but transsexuals? They may as well have been aliens. She wouldn’t have been comfortable with it. I really don’t know if her religious views entered into it. Bruce actually went to church more than she did.

I approached the advocacy group PFLAG to get their take on any attempt by Kris to suppress her husband’s trans feelings by encouraging Bruce to heal himself through prayer when he still lived as a man. The group’s northeast regional president Amy Mesirow was troubled by the allegation. “I share PFLAG’s stance that people’s sexual orientation and gender identity are natural, and cannot be ‘prayed away,’ ” she said. “I imagine that any effort by Kris Jenner to have Caitlyn pray to cure herself would only serve to damage her emotional and mental health, as it has other LGBTQ people who have been asked to do this. When transgender people of faith are told that God sees them as being sick, this only compounds the harmful messages society sends them every day about who they know themselves to be.”

Another longtime advocate told me how concerned she was in the days after Bruce first went public about his desire to become a woman. “Word in the community was that Kris tried to get Bruce to suppress his true desires and to cure himself by prayer and to remain a man,” the respected advocate who asked to go by the name of Sheila told me. “That would have been very hard on Bruce. And from what I’ve heard Kris was not the only person doing that. There were others before her. Bruce wanted to transgender for a long time. The world would have seen Caitlyn a long time ago if there were not people like Kris trying to get him to heal himself through prayer and to suppress his true path in life.”

Before the dust had even settled on the Diane Sawyer interview, Vanity Fair announced that it would feature Jenner on the cover of its July issue. When it was announced that famed photographer Annie Leibovitz was shooting a “special” cover, speculation began to mount that the issue would be his official coming out as a woman. In the Sawyer interview, he had referred to his female identity as “her” but had declined to dress as a woman and had asked that he still be called Bruce. The New York Daily News had secretly captured a photo of Bruce in a dress back in April, but there had been no official appearance as a woman to date.

Now it appeared that he was going to use the respected magazine to unveil his new self. Sure enough, in advance of publication, the magazine leaked a stunning cover photo, taken by Leibovitz, featuring Jenner dressed in lingerie—a low-cut corset—and full glamorous hair and makeup. Days later, the issue hit newsstands with the headline, “Call Me Caitlyn.”

“He says goodbye, she says hello,” read the caption announcing that Bruce Jenner was now a woman named Caitlyn. It’s hard to imagine that anything could have topped the dramatic coming out of the Diane Sawyer interview, but this appeared to create even more buzz as the world marveled at the new look.

By the time Caitlyn sat down with Buzz Bissinger for her first interview as a woman, it was clear that her taped reunion with Kris a few weeks earlier had not cleared the air between them. If Bruce had subtly implied to Diane Sawyer that his ex-wife was less than supportive, Caitlyn now added more detail.

“The first 15 years I felt she needed me more because I was the breadwinner,” she explains of Kris.

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. People would see how I got mistreated. She controlled the money . . . all that kind of stuff.

When the reporter asked Kris for her side of the story, she told him that she couldn’t understand how her husband, after a strong marriage, could just say “I’m done now” without explaining his gender-identity issues to her until after they had separated. “It was, like, the most passive-aggressive thing I think I’ve ever experienced,” she said.

Within hours after Caitlyn’s unveiling, she was being hailed as a hero—by the 700,000-strong transgender community; by her fellow celebrities, who were falling all over themselves to Tweet their support; and by the media, who praised Caitlyn’s “brave” and “courageous” coming out.

“I’m so happy after living such a long struggle to be living my true self,” she posted in her inaugural Tweet as Caitlyn. “Can’t wait for you to get to know her/me.” Within twenty-four hours, she had amassed one million followers, the fastest in history to achieve that milestone.

Instead of rushing to cash in on her new popularity, she let it be known that she planned to dedicate her new position to advocacy for the trans community and to help end discrimination against this marginalized group. A 2013 report released by the Human Rights Campaign, among other groups, had found that transgender workers had an unemployment rate double that of the general population. More troubling was a study that showed the attempted-suicide rate for transgender women and men was an eye-popping 41 percent, compared to 1.6 percent in the general population.

Caitlyn went out of her way to stress that she didn’t consider herself a leader just because of her celebrity. “I would like to work with this community to get this message out,” she said. “They know a lot more than I know. I am not a spokesman for this community. I believe we can save some lives here.”

I was curious myself to know how grassroots trans people viewed Caitlyn’s coming out and whether they thought it genuinely benefitted their community. Although reaction from community leaders had been largely positive since she’d announced her transition, there had been some backlash as well. The most glaring criticism surrounded the stunning Vanity Fair cover in which Caitlyn had widely been described as beautiful and glamorous for her lingerie shot.

“Caitlyn Jenner is just Kardashian 2.0,” complained Zoey Tur, the trans correspondent for Inside Edition and host of the radio talk show He Said, She Said. “I’ve received well over 100 messages from trans women who said they didn’t want to transition anymore because they feel that they can never live up to the Caitlyn Jenner ideal.”

I wasn’t particularly interested in hearing what so-called community spokespeople thought of Caitlyn. I wanted a grassroots perspective. I had once gone undercover as a gay actor to infiltrate Scientology, but this was definitely different. Now I resolved to pose as a man wishing to transition into a woman. With a little research, I found out about a trans support group that holds bimonthly meetings in Miami. I decided to attend a session. Posing as a gay person had been easy. Gay men look like everybody else. But if I were pretending to be trans, would I need to dress like a woman or at least put on some makeup or jewelry? It didn’t take me long to discard that idea. I didn’t want to go over the top and maybe give myself away. Besides, after a little research, I discovered that many trans people live their lives undetected before they fully transition, especially at work.

The group didn’t publicize their meeting location, perhaps out of fear of harassment. But after making indirect contact, I was finally emailed a location.

I was greeted warmly by a trans man with short hair who appeared to be the facilitator. When I arrived there were only two other people, including an older woman, and I kept expecting more people to show, but it soon became obvious that we were the entire meeting. I introduced myself, using the pseudonym I always use when I go undercover, Al Newman (short for Mad magazine’s Alfred E. Newman, my childhood inspiration.)

The facilitator, E.R., kicked off the meeting by answering a question that somebody had asked him earlier: how a person typically knows when they’re trans.

“Not every trans person knows very early but many do when they’re little, as little kids. Some of us have that memory of ‘I knew then’ and some don’t, and I don’t ever condemn people for not knowing when they were little, but I knew. I didn’t know I was trans, because there’s no words for that when you’re a little kid, but you just know that you’re different.” He then asks me to introduce myself.

I tell the group that I’ve known for a long time about my gender identity but I never had the guts to come forward. “I think what convinced me finally was the Caitlyn Jenner stuff,” I tell them.

E.R. nods knowingly. “You’re not the only one I heard that from,” he said. “That’s made a big difference for a lot of people, not just on an internal and personal level, but societally. I’ve seen changes in the last month that are big. People on Facebook, Twitter, saying, ‘I would have thought this person was a freak if I hadn’t watched the Diane Sawyer interview. It must be so hard, what she’s been through.’ People who before only thought of trans people as crazy or freaks or whatever got to see this whole other side of somebody being very authentic, very honest, and somebody who they can relate to as a very famous athlete, as a man, and all of a sudden it gave credibility to the issue, it gave weight to our feelings; it’s just been tremendous. Certainly there’s been plenty of haters as well, but I prefer to look at what’s positive and what’s come out as positive for the movement.”

He then congratulated me on “taking a big step.” The other man introduced himself as Enrique. He introduced the woman beside him as his mother. I told him I thought it was cool that he brought his mother along. The middle-aged Latina woman said that it wasn’t easy at first when her son told her he wanted to be a woman. “I was a little homophobic,” she admitted. “I’m from Haiti and I had a Catholic grandma and my priest and the nuns at school taught me that being gay is wrong.”

“You were very homophobic,” Enrique tells her. “Thank you for coming. It means a lot.”

“You’re my baby,” she replies.

“Don’t call me that,” he protests.

“I don’t know whether to call you my little boy or my little girl,” she says sweetly.

“She’s also my ride,” he notes. “I don’t currently have a driver’s license.”

“Because I love you, I’m really trying to be supportive,” his mother adds.

Enrique turns to E.R. and asks, “How does the process go of obtaining hormones and all that?”

“That’s the easy stuff,” E.R. responds. “People think that’s the hard stuff. The hardest part is getting to your own internal acceptance, feeling you’re going to be safe. That’s much harder. Some places make you get a letter certifying you’re trans, which I find very oppressive. Some places just make you sign a letter which they call ‘informed consent,’ where you say you’re aware of the risks of the medications and you agree to the risks. Some regular doctors will do it but I recommend going to someone who has experience. They do a very basic psycho-social, which is how you get a letter. There are challenges.”

He says that he went to a regular OB/GYN when he wanted to transition. “And for transitioning male to female, it’s actually a very inexpensive prescription. It doesn’t cost a lot. Hormones are easy; surgery is a little more complicated. Breast augmentation is comparable to what any other woman would pay. Thirty-five thousand dollars. But surgery is more complicated; you want to put some thought into it.”

I asked the facilitator how he worked up the courage to come out as a man.

“I was part of a sorority and I had nothing in common with them,” he recalled. “They were always like, ‘Let’s do our hair, our nails, and what about my boyfriend?’ and I couldn’t identify. I mean, I love men. I’ve always been attracted to men, so my orientation and gender are not necessarily tied in together in that way. A lot of people think trans men must date women but I never have. So I’ve always been attracted to the guys and always had that conversation with them, but that’s all we had in common. And then when they found out I was trans, they’d ask, ‘Well, don’t you like women? You’re a lesbian, right?’ ”

He said he recommends taking everything in small steps.

“First I cut my hair, then I started wearing boy’s underwear. Then I started wearing ties,” he explained, but he pointed out that he has a very close friend who just went “balls in.”

After we finished laughing, he recalled, “She dived in. She didn’t test the water at all. She dove in and couldn’t be more happy. Starting hormones when you’re transitioning from male to female is slower. For us, within a month, our voice starts to change, but for you all, the changes are a little bit less physical, unfortunately, and a little bit slower, so you could start hormones and for months nobody would even know anything is happening. If that’s something you want to do; some people don’t want hormones, they don’t want surgery.”

I asked whether he had any recommendations for a clinic where I could get the procedure done. He told me he had simply gone to an OB/GYN but noted that there are a number of clinics in South Florida that specialize in the procedure. He offered to refer me. The group had been very helpful in providing perspective, so much so that I felt a little guilty about deceiving them. When I left the meeting, however, I decided that if I were to gain any insight into how Bruce became Caitlyn, I would have to head to her backyard.

Just days after the Vanity Fair issue hit the stands, I decided to go undercover at the same Beverly Hills clinic where Bruce had his Adam’s apple removed back in 2014. When I landed in Los Angeles, I had my assistant Grace call the clinic on a Tuesday to try to book an appointment. But my plan hit a snag almost immediately. She told the receptionist that I was only in town for a few days, but she was informed that I couldn’t just waltz in the same day and make an appointment. She said I’d have to fill out some forms before receiving a consultation. The usual wait time was several weeks. When Grace informed me that she was rebuffed, I told her to call back and demand an appointment for the next day. She was instructed to say I was a Middle Eastern prince with unlimited financial resources and that money was no object. That seemed to do the trick. The receptionist informed Grace that I could come in the following day.

When I arrived at the Beverly Hills Surgery Centre of Excellence on La Cienega Boulevard, I noted that it was just a few doors away from both Larry Flynt’s towering Hustler building and the former offices of private investigator Tom Grant, with whom I had collaborated on my first book, about Kurt Cobain, almost two decades earlier.

The first thing that struck me upon entering the elegant clinic offices was a copy of the Caitlyn Jenner Vanity Fair issue lying out in the open on the receptionist’s desk. I told her that I grew up in Canada but had moved to Israel when I was young because I had ancestors who were part of the Israeli royal family. I took a deep breath, hoping she wouldn’t realize that there is no Israeli royal family. She didn’t.

She informed me that Dr. Malek, the surgeon whom my sources told me treated Caitlyn Jenner, was out for the day. His assistant, Rozeta Avetisyan, a late-twentysomething attractive woman, came out to greet me and informed me that she would perform the consultation. When I discovered that she was Armenian, I wondered whether there was a Kardashian connection, but I hesitated to ask. After some small talk with Grace, we stepped into the examination room. I told Rozeta that I wanted to be “just like Caitlyn Jenner” and asked her if she knew anything about her surgery.

“We never talk about clients,” she curtly replies. I take that as an admission that Caitlyn was treated by Dr. Malek. I tell her I had noticed the Vanity Fair cover on the reception desk and ask her how she thought Caitlyn looked on the cover. “I prefer not talking about it,” she says. “But the cover looks very good.”

She reveals that Dr. Malek is a world-class painter and she is eager to show me his work, but his paintings are located on the second floor, which is closed off for a few days for renovation. “Dr. Malek is an artist; he and his family are very serious in painting and creativity,” she tells me. “That’s why he is so good at surgery. He’s very specific and detailed. He takes his time with every procedure. If you go online and type Malek Masoud, you’ll see all his paintings. Him, his daughter—they’re all painters.”

Rozeta seats me in a small room and starts examining my face and neck. After only a few moments, she tells me it is “essential” to get some work done. Pointing to my neck area to the left and right of the Adam’s apple, she says I need liposuction there.

“See this part and this part you can get this done. They’ll clean it very nicely. As for the Adam’s apple, he [Dr. Malek] needs to see it. He can shave it and do everything because he’s a plastic and reconstructive surgeon.”

Excusing myself for a moment, I fetch the Vanity Fair and point to the photo of Caitlyn on the cover, asking if he can shave it like that. “You want it like that?” she asks. I nod in the affirmative. “Yes, if you talk to him, he can do that for you.”

She tells me the procedure will likely take between three and five hours and the recuperation would be around five to six months. “It varies from patient to patient,” she explains. “Everybody recovers completely differently. You have to come in three days after the surgery and after that every week so we can follow up and see that everything is right.”

Next, I inquire about the price. She tells me liposuction would be two thousand dollars and that the Adam’s apple shave will be “substantially more” but will not commit to a figure. “When you see Dr. Malek, he will give you the exact price.”

Next I tell her I want breast augmentation. She examines my chest area and tells me it won’t be a problem. I ask her the price for this procedure and this time she has no hesitation replying. “It goes from six, seven, eight thousand. It depends on the size.”

Meanwhile, Grace asks Rozeta if she can video some of the consultation so we can go back to the hotel and make a decision. I tell her I’m staying in the penthouse of the Four Seasons Hotel in Beverly Hills. In actuality, I’m staying at a $180-per-night hotel on the seedy part of Third Avenue in lower Beverly Hills. Grace tells her that I am willing to pay the maximum price.

“He, or, may I call her ‘she,’ wants the best in the world,” Grace assures her. “Price is no object.” Rozeta has no objection to us filming. As Grace trains her video camera, Rozeta also takes out a camera and starts taking digital photos of my neck from different angles. I ask her if I can get the surgery performed the next day. “No, not tomorrow,” she said. “You need to get your blood work done and after that I can put you in for next week.”

She tells me that before the surgery she’d show me pictures of people they’ve worked on. I ask her if there were any celebrities. “We do but it’s very confidential,” she replies. “It’s very safe. You have nothing to worry about. He’s been in business for over forty years. He knows his stuff.”

Before we leave, she tells me she is optimistic they can help me on my “journey” and that surgery will help turn me into a beautiful woman.