She Is Cait, and I Am Not: Face to Face With Jenner

As the second season of I Am Cait approaches, Jenner reveals her goals for the future, which include becoming "trans ambassador" to President Ted Cruz.

Winding my way round dead man’s curves at unsafe speeds all the way up a Malibu mountaintop to meet Caitlyn Jenner, I asked myself, Who would live here except a recluse? Cut off from the rest of the world, high above it all, looking down from her own Mount Olympus — is there more than a metaphor at work here?

Or is she just a rich broad who likes her privacy and can afford to live above the clouds, and why not?

“Yes, my journey is different than most people,” Jenner tells me, as we begin our conversation discussing her docu-series on E!, I Am Cait, which returns for a second season Sunday. “To be honest with you, I don’t really talk to the media. This is very rare,” Jenner reminds me early in our hour-long conversation in her fluffy white living room.

Caitlyn Jenner’s home is California contemporary meets Hearst Castle, even more incredible than it appears on television, and yet somehow extremely comfortable, feminine, and luxuriously styled without being gauche or extravagant. It’s chic, modern, and has a view that I imagine is second only to heaven. Seeing this place on TV, no matter how big your screen is, just can’t compare.

My goal for the past year has been to meet the woman who has been elevated by the mainstream media to the status of transgender icon, whether deserving or not — many would say not. To learn she knew who I was caught me off guard, because even though I may have a byline and achieved some notoriety a few years ago, I don’t consider myself famous. And I don’t consider my transition to be anything like anyone else’s, even though, like Jenner, I lived a double life for years. I was dishonest with my wife — and myself — about my needs, and I am what some people refer to as a “late transitioner.” I’m 51 and didn’t come out until I was 49. Jenner came out last year and is now 66 — and looks fabulous. I've never felt more compelled to lose weight.

“What I have learned in this community is every journey is different. No two stories are the same. Not even close,” Jenner says as she leans in and looks me in the eye. I can feel her intensity from where I'm sitting, just three feet away.

One of my first questions to Jenner addresses widespread tabloid rumors that she is detransitioning and going back to her old life and male presentation. And when I say widespread, I mean even a colleague in my LGBT-dominated office asked me, "Is it true?"

Jenner laughs, loudly. "No way! This is a one-way trip, sister. I ain't never going back!"

As some trans women do, we chat about surgery. Jenner mentions that she had facial feminization surger) and we agree the rest is "nobody's business" but ours, and we can't imagine why anyone would want to know — unless their intention is to be intimate.

We talked a lot about why we are who we are. Jenner wears her first name on a delicate gold necklace, which I thought was interesting, as if there could be any mistaking that she is Cait.

“I did this, number 1 reason, is to be true to myself. You cannot do this unless you are true to yourself," says Jenner. "No matter any of this B.S. that is going on around me. But if I am true to myself and I wake up happy, then in doing that, can I make a difference? That’s what I’m trying to do. Even though the show is called I Am Cait, it’s not about me. It’s about this community. It’s about the people in this community. It’s a platform."

Despite her notoriously conservative beliefs, Jenner reveals that she has a stereotypically California hippie vibe.

“Everybody needs to kind of do their own thing. All we’re trying to do is be happy. We want to wake up in the morning with a smile on our face. I woke up the other day,” Jenner tells me, “and I was getting ready, and I thought, I was just happy. And I haven’t had that in my life in a long, long, long time. Just happy to be me. No more secrets. You know the feeling?”

I do.

Six weeks ago I became a widow. I had been on my way to being happy in the way Jenner described it just eight months ago: living my truth, sad to be separated from the love of my life and our children, but delighted to have found myself and a new career in Los Angeles. I was eager to start my own California adventure. On June 26, the Supreme Court announced its ruling on marriage equality, and I was the hub in the wheel of our coverage of the biggest story of 2015 when I received an urgent text from my spouse. I called her, and she revealed she was diagnosed with cancer. That day was the turning point in my life, the roadblock that caused me to make a U-turn.

On the twisty road that leads to Cait, I apparently missed a turn, hence I was speeding; I was trying to make up for lost time by pressing my four-inch heels down hard on the accelerator, even while rounding hairpin turns. The headline to this story might have read “Trans Woman Killed on Way to Meet Caitlyn Jenner.” That would be no surprise to anyone who knows my driving record — I’m famous in my family not for my transition but for my well-earned nickname: “Crash Ennis.”

Forty years ago, Jenner made a name for herself with her incredible decathlon achievement in the 1976 Olympic Games. And three months to the day after she won the gold, she lost her only brother, Burt, 18, in a car crash 15 minutes from where I now reside in Connecticut.

And no, although our transition stories do have some parallels, I did not take time to compare notes about car crashes with the lady in question. Because this isn’t just any lady or any interview. Other than one with a trans man who is an aspiring journalist at age 17, and one on stage at a fundraiser with ESPN's Christina Kahrl, our interview is the first Jenner has ever had, one on one, with a transgender journalist for a story.

Perhaps it’s because she has not been universally embraced by trans people.

“The biggest criticism has come from within the community,” she tells me. “It’s not the cis [nontransgender] girls out there or the cis guys. They love what we’re doing here.”

Jenner admits that unlike most celebrities who will have “their people” deal with the media, she is not shy about dialing up journalists to discuss their articles about her.

In fact, she considers herself an expert in managing media relations, after several decades of interactions and her last marriage, to public relations maven Kris Jenner. “I know the media. I know how the media works, and I know how to play the game,” she says. And in a very unusual exchange, to be filed under Six Degrees of Trans Separation, Jenner learned that two of the writers she’s called are friends of mine who are trans, both writers frequently featured in The Advocate: Brynn Tannehill and Amanda Kerri.

To Tannehill, who penned an “open letter” to Jenner suggesting she needed to lower her profile, she said, “My only criticism of your article is that you don’t know me. You’ve never talked to me. You’ve never met me. You don’t know what my intentions are. So that’s why I called today. I want to get to know you.” Jenner says they spoke for 45 minutes, and she had an even more positive conversation with Kerri, who defended the reality star as being as “problematic” as all of us.

Kerri, who is a stand-up comedian in Oklahoma City, told me Jenner swiftly became very personal with her, assuring her as a new friend that she never intends to be malicious when she misspeaks, complained about the media, bragged on her children, and discussed her desire to come out sooner than 65, and what stopped her. That seemed to me to be quite a lot in a first, "get to know you" conversation. But given that we are on Mount Olympus, where Jenner lives high on a hill above Malibu, isolated from all of us, I can better understand her desire to connect, to make contact with ordinary trans folk.

We’ll see Jenner go face to face with some very angry critics in season 2. She was confronted by protesters in Chicago last November outside a fundraiser for a social services program for transgender people. The demonstrators shouted that she doesn’t represent trans people who aren’t white or wealthy. “Three people, one with a bullhorn, just yelling and screaming,” Jenner says, and recounts that she walked right up to the organizer — with cameras rolling. “She wouldn’t show her face, and the media loves that stuff. I’m in there raising money for Chicago House, which is helping trans women of color find a place to sleep.”

This sentiment persists, even though Jenner has done an enormous amount of work to benefit others, both through her show and privately. Yet to many of the millions who watch her, she appears aloof and not in touch with everyday folks who snack on fries from the drive-through before they get home, who go bowling or hang out with a pitcher of beer at the local watering hole with friends, complaining about how much they hate their jobs.

“My job,” says Jenner, “is to do my damnedest not to give [the media] a story. I know they’re out there, and they’re looking for a negative story. Especially this season, what I want is all the girls who are on the show to be in somebody’s home who has never met anybody who is trans, and for them to absolutely love these girls.”

She’s not talking about her daughters.

The “girls” include Zackary Drucker, Chandi Moore, Candis Cayne, newcomer Ella Giselle, and Jenny Boylan.

“They’re intelligent, they’re cute, they’re adorable,” says Jenner, who tells The Advocate she was looking to bring in someone new, when she found Ella Giselle, 18, the trans daughter of a longtime friend.

“I met her and I thought, she would be just a great addition. Why? Because she is kind of the new school. Eighteen. Transitioned between junior and senior years of high school, came back in senior year of high school as Ella. That’s tough to do in high school.”

Giselle replaces Her Story’s Jen Richards, who departed the show during season 1. Giselle also potentially brings E! a younger, highly sought-after demographic to I Am Cait's audience.

Teens today only know Jenner as Cait, or as the woman who is the dad on Keeping Up With the Kardashians, not coincidentally produced by the same company and on the same network as I Am Cait. One reason, Jenner says, is to be able to have her kids on her show and to appear on theirs, something she says is of enormous importance to her. And because of her affection for young people, I reached out to students at my local middle school who have a trans classmate. My spouse taught there. I asked, through my daughter who is a student, if these students would like to ask Cait a question. With their parents’ permission, I put some questions from those eighth-graders to Jenner.

“When did you start realizing you were different?” asked Anne.

“The first time I started dealing with it, I had to be 10 years old, maybe 11,” Jenner says. “I was fascinated by femininity, and not knowing why. I had an older sister and my mother, she says, looking back, ‘This is why you never wanted to wear all those clothes I bought you. I wonder if I had bought you a dress you would have worn that.’ I said, ‘Mom, let’s not even go there. We’re talking 1960s, 1970s, there wasn’t even a name, a word for it. For me, it was ‘Stay quiet. Don’t tell anybody. This is your secret, and keep your mouth shut.’”

Jayce asked, “What’s your response to people who talk down to you for fighting for LGBT [rights]?”

“Nobody has talked down to me — to my face. I get nothing but love and support every place I go. But the Internet, ok? You will get stupid statements online, this and that, on and on, and the media is gonna run with something. I really can’t deal with that, I just have to stay positive.”

Does she surf the Internet? “I did for a while, I would read comments. And I would say to myself, ‘That’s so stupid!’ The next one, ‘Geez! They don’t get it!’”

What it comes down to for many of Jenner’s critics in social media is her privilege, which she acknowledges.

She bought a plane recently, and says she flies just about every day. Her favorite sports are auto racing and golf, both as a spectator and competitor. Just yesterday, she moved her locker from the men’s changing room at the Sherwood Country Club to the ladies'.

She laughs in relating the story that she was invited to compete in a golf tournament tomorrow by a male friend, but the club turned her away — because it’s a men’s-only tournament. Her goal, she says, would be to hold a tournament in which trans women could compete.

"Golf is a social and a competitive sport for me. I enjoy playing with all types of people, and I'd love to play with a group of transgender women sometime too."

But away from the links and the cameras, does she meet your average transgender person? “The trans Jane Does and John Does?” I ask.

“That’s what season 2 is about,” Jenner says, revealing that she and her friends traveled for a month on a tour bus from Los Angeles to the Grand Canyon, Santa Fe, Tulsa, Chicago, Des Moines, Kansas City, St. Louis, New Orleans, and Houston. “All the people we met were fabulous, articulate, trying to make it better in their community for other people. They started programs, developed programs in the community, which never existed before. It was very, very rewarding.”

It was also contentious when the conversations aboard that bus turned to politics, which Jenner says they often did. “It got heated! Especially with poor little me, who’s the lone Republican conservative against all the liberal Democrats.” So heated, Boylan can be seen shouting “That is a lie!” at Jenner, at one point even swatting her head with a rolled-up newspaper.

And drama is sure to ensue when Jenner meets Hillary Clinton on the campaign trail. The only candidates she spoke about with The Advocate, however, were Republicans.

“That’s just political B.S.” she says of Donald Trump’s recent inability to disavow David Duke and the Ku Klux Klan in an interview with CNN’s Jake Tapper. So who does she support for the nomination? I ask.

“I like Ted Cruz,” she declares. “I think he’s very conservative and a great constitutionalist and a very articulate man. I haven’t endorsed him or anything like that. But I also think, he’s an evangelical Christian, and probably one of the worst ones when it comes to trans issues.”

“I get it. The Democrats are better when it comes to these types of social issues. I understand that.” So why support Republicans? “Number 1, if we don’t have a country, we don’t have trans issues. We need jobs. We need a vibrant economy. I want every trans person to have a job. With $19 trillion in debt and it keeps going up, we’re spending money we don’t have. Eventually, it’s going to end. And I don’t want to see that. Socialism did not build this country. Capitalism did. Free enterprise. The people built it. And they need to be given the opportunity to build it back up.”

Jenner reveals she met Cruz prior to her transition, more than a year ago, “and he was very nice.”

“Wouldn’t it be great, let’s say he goes on to be president,” she tells me in relating a conversation on the tour bus. “And I have all my girls on a trans issues board to advise him on making decisions when it comes to trans issues. Isn’t that a good idea?”

“You’re going to be Ted Cruz’s trans ambassador?” I respond.

“Yes, trans ambassador to the president of the United States, so we can say, ‘Ted, love what you’re doing but here’s what’s going on.'”

She wasn’t joking.

To those who think she needs to change her political affiliation or stop her daughters from calling her “Dad” — the same name my three children call me to this day — she has an answer, based on a scene in an upcoming episode shot in Iowa.

According to Jenner, Giselle addressed Jenner’s Christian alma mater, Graceland College, and declared to the students listening, “I am still the same person. I still enjoy a lot of the same things, and there’s no reason why I should ever give that up.'”

“If I enjoy going out with my kids,” says Jenner, "or I enjoy going racing a car, I will still go race a car. OK? Girls drive race cars. Of course they can! Why can’t they? I can take all the fun things that ol’ Bruce did, and I can still do them today.”

But then Jenner reopened a can of fashion-worms when she stood by her preference to “look good.” She recognizes she misstepped when she said she didn’t want to “look like a man in a dress.” “That was my own personal statement, and of course the community went, ‘Wait a minute! What about all the ones who don’t care about that? About passing? There are some who really want to look like a man in a dress. There are so many variations in our community of how to deal with yourself.’ But I was talking about me personally. I get photographed every day of my life. Not a day goes by that a paparazzi [doesn't photograph] me or a person wants a selfie.”

Yes. I am guilty.

But Jenner’s point is, looking good is important, and not just to her.

“I think it’s important for this community to present yourself well, to feel good about the way you look. If you walk out the door and you feel good about the way you look, no matter what that look may be, for you, you feel good. I like that feeling.”

And what about those people who don’t? Jenner tells me she is especially focused on them right now. She recalled a trans girl she met recently who she felt was “struggling” with her presentation, based on her male-appearing physicality.

“This is the person I’m fighting for. My life is great; I have no problems. She would have a hard time walking down the street and not being harassed. People will look at her and say, ‘What is that?’

“I said, ‘what’s your name,’ and she said ‘Victoria.’ I said, ‘It’s so nice to meet you, Victoria.’” They chatted a bit, Jenner says.

“As she walked away, I wondered, What is her life like? Season 3, I really want to explore gender-nonconforming and people who either have a very hard time or cannot physically present as the gender they truly are. How do they feel about that? They are so driven to be themselves, what happens when they go to the grocery store?”

As for criticism by blogger Monica Roberts, that in her travels Jenner should have met with homegrown activists in Houston, including trans people of color, she says that even without including them, the Bunim-Murray production team already “literally has thousands of hours” of video for the eight episodes running 44 minutes each, and most of that won’t make the cut.

And to those who criticize her for not contributing her wealth to the plight of transgender people who are underemployed or earning less than their cisgender peers, or who think they or someone else not so famous would be a better focus of a TV series, Jenner says, she hears you.

“I understand that they would like to financially be better off or have their own television show and all that kind of stuff. I can’t help everybody. But I’m trying. I’m trying.”

Jenner notes that she’s launched her newest philanthropic venture, reported by our sibling publication Out: She has teamed up with MAC Cosmetics for a campaign that supports the brand’s transgender initiative. One hundred percent of the sales from Jenner’s signature lip color, Finally Free, will benefit the MAC AIDS Fund as grants to “organizations and programs dedicated to improving transgender lives.”

That led her back to her goal for season 2 of I Am Cait:

“I hope that for the first time, someone will know a trans person that is happy, that is successful — I think that’s important — and that they would just like to hang out with me or my girls. I think that makes it better for everybody. I think it normalizes this experience as much as it possibly can.”

I ask her about that concept. Does “normalize” refer to the perspective of people who consider trans people like us “freaks or weirdos?”

“Yes, absolutely! And we’re not. We’re people. Most people don’t know us. Don’t know anything about us. This has been going on throughout history. This is nothing new; it’s part of humanity. It is a small portion of humanity. But we are there. And there’s a lot of work to be done. In my soul I am going to do what I can for me and for the community, and hope for the best.”

We said our goodbyes, she wished my children and me well, and I got into my car. But before I started down the mountain, I paused to watch the sunset from above the marine layer over Malibu. And I thought, someday, I will find the serenity she has, and just maybe, finally wake up happy. “Life is a journey and not a destination,” goes the saying. And so I decided to take that trip downhill, from Jenner's Xanadu back to the Pacific Coast Highway, savoring the view at a leisurely pace.