The True Story Behind Caitlyn Jenner's Transition

What's the true story behind Caitlyn Jenner's transition? The Olympian had always struggled with her gender identity, according to an interview with ABC News' Diane Sawyer. Jenner knew from the time she was just a kid that she was in the wrong body. "I would say I've always been confused with my gender identity since I was [small]," she said of her childhood. 

Jenner grew up in Tarrytown, New York; her father worked as a tree surgeon, and her mother was a stay-at-home mom. Jenner told Sawyer that she was so energetic as a child that her dad gave her the nickname "Bruiser." 

With that energy, Jenner ultimately went on to do great things in this world — from becoming an Olympic gold medalist to raising ten hugely successful children to being a voice for the transgender community. She couldn't have known as a confused young kid just how much of an impact her journey would have on others. So without further ado, here's the true story behind Caitlyn Jenner's transition.

Caitlyn Jenner told ABC News' Diane Sawyer in an interview that she first tried on a woman's dress in the late 1950s, when she was about 8 or 9 years old — about the time that researchers believe kids start familiarizing themselves with their own identities. Jenner used to sneak into her mother's and sisters' closets to try on their clothes, but she didn't know why she was feeling compelled to do it, and was always nervous about getting caught. "I marked the closet so when I put it back I could put it all back, everything back in the exact same spot so I wouldn't get caught," she confessed. "It just made me feel good."

Jenner would also wear a scarf over her head to cover up her short hair, and wander around outside. At the time, she didn't know "what's up," because she couldn't find any information to help her to unpack her inclinations.

Caitlyn Jenner spent most of her teen years struggling with the fact that she identified as heterosexual, but didn't feel like her gender identity was male. It was in high school that she had the revelation that her sexual orientation was a totally different thing from her gender identity. "I was never attracted to the guys or any of that kind of stuff," she told ABC News. "Because sexuality was totally different from what my issues were — I always felt heterosexual."

Jenner would look at the boys in her class with envy, jealous that they seemed to be comfortable in their own skin, as she said in her interview. She wondered what it'd be like to wake up in the morning and just be herself instead of "stuck here in the middle." She'd ask herself, "Wouldn't that be a nice way to go through life?" Still, Jenner didn't come out about her gender identity for quite some time — so she spent all of her youth wondering.

One of Caitlyn Jenner's greatest accomplishments was making the Olympic team for the 1972 Munich Summer Games, landing in tenth place for the decathlon, according to Team USA. She immediately started training for the 1976 Olympics in Montreal after that, setting a world record for the points that she earned, becoming one of the world's greatest athletes. Jenner trained for six to eight hours every single day with a hurdle in her two-bedroom apartment, according to The Washington Post.

Jenner was very competitive in sports, as she told the BBC. "When I got into sports, it became more important for me to succeed at sports and work hard at sports because of all these [gender] issues," she said. But when she won her Olympic gold medal, it wasn't all bliss. "I remember getting up the next morning and walking to the bathroom without a stitch of clothes on," she continued. "The gold medal was sitting there on the table. I put it around my neck, looked in the mirror and asked myself... 'Am I stuck with this person the rest of my life?'"

Caitlyn Jenner married her high school sweetheart, Chrystie Scott, with whom she had her first two children, Burt and Cassandra Jenner. Caitlyn and Cassandra's relationship has gotten exceedingly closer, according to People. 

Jenner told ABC News' Diane Sawyer that it was Chrystie who was the first to really know about her gender identity struggle. But Chrystie didn't quite understand the extent of it. "I didn't go heavily into it back then," Caitlyn said in the interview. "I said, 'These are my issues. This is what I deal with.' And they think I do a little cross-dressing."

While Crystie and Caitlyn ultimately got divorced in 1981, Chrystie told ABC in a statement that she fully supports Caitlyn in her transition. She said that Caitlyn has "every right to live the last quarter of [her] life as [her] authentic self." She also said that she prays for Caitlyn's happiness for the rest of her journey.

Caitlyn Jenner married her second wife, Linda Thompson, in 1981. The couple had two children together, Brody and Brandon Jenner, according to Jenner's piece on Huff Post. Apparently, Thompson and Elvis Presley (her ex) were watching Jenner win the Olympics on television when she ironically joked to Elvis that she'd marry Jenner one day. Then she ran into her at a celebrity tennis tournament in the spring of 1979 at the Playboy Mansion — and their relationship blossomed from there.

Jenner and Thompson ultimately got married at the beachfront home of Alan Carr in Hawaii. "[Caitlyn] and I spent our days living at the beach, jet skiing, walking on the beach every morning with our coffee, sailing on a Hobie Cat, playing tennis and otherwise just enjoying each other and many of the same activities," she wrote. "I thought we lived a pretty idyllic life."

But the pair ultimately got divorced, largely because of Jenner's struggle with her gender identity.

Just after Caitlyn Jenner and her ex-wife Linda Thompson got divorced in 1986, she sought help from a doctor for the first time, as she was struggling with serious depression. At that time, she started taking estrogen, got a nose job, and underwent electrolysis to remove her beard. She also started to develop breasts, telling Today that she was a "good solid 36B," which she said was difficult to hide.

Eventually, Jenner decided to come out to her sister, Pam Mettler, about her gender identity. Mettler was the first family member to learn about what was going on in Jenner's private life. "[She] said, 'I have a family matter I would like to talk to you about,'" Mettler told ABC, admitting that she was shocked to hear the news. "[She] told me that [she] had always felt that [she] should have been a girl. I said, 'What?' I couldn't believe it. I didn't understand it."

Caitlyn Jenner married Kris Jenner in 1991. The duo met on a blind date and got married in less than a year, according to The Guardian. While their marriage didn't end up lasting, Kris still played a major role in helping Caitlyn get her career back on track after she retreated from the public for some time. Kris landed Caitlyn roles in fitness infomercials and on talk shows, and even helped her become a motivational speaker. And of course, they filmed over 400 episodes of Keeping up with the Kardashians – which has changed a lot since season 1 — together along with their many children. 

However, Caitlyn admitted to ABC that she always felt like a liar in the public eye. "I probably was not as good at saying, you know, 'Hey this is really down deep in my soul and I don't know if I can go further like this,'" she told ABC. According to Caitlyn, Kris would allow "cross-dressing here, cross-dressing there," so long as she didn't see too much of it.

In 2014, after Caitlyn and Kris Jenner split up, Caitlyn knew that needed to re-start her gender transition, as she was fighting debilitating depression at times. She even pondered ending her life, as she told ABC, telling herself that the easiest thing to do would be to go through with that. But then Caitlyn told herself, "I can't do something like that ... I want to know how this story ends, you know? How does my story end?"

To that end, Caitlyn started hormone therapy for the second time. She also started to have some gender confirmation surgeries done, little by little. For starters, she had her Adam's apple shaved down. However, when a tabloid journalist spotted Caitlyn leaving the doctor's office, the news of her transition started going viral in the media; Caitlyn wasn't quite open about her transition when the media started speculating.

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Having her Adam's apple shaved down wasn't the only facial-feminization procedure Caitlyn Jenner had, according to Vanity Fair. In fact, she was under the knife for 10 hours, total. But, despite knowing she was a woman for her whole life, Jenner had a short panic attack after the surgery, wondering if she made the right decision.

Jenner had never had a panic attack before in her 65 years on the planet. But at that moment, she walked into the hallway and paced back and forth for about 15 seconds, thinking to herself: "What did I just do? What did I just do to myself?"

Jenner had committed to her transition for the first time in her life — and that's a big commitment. Fortunately, her gender counselor assured her that second-guessing her decision was simply human nature, and probably had something to do with the pain medication she was taking as well. With her mind at ease, Jenner didn't think twice about her decision ever again.

Caitlyn Jenner was 65 years old when she officially came out to the world as a transgender woman. And while she waited a long time to transition, she's happy that she ultimately did it, as she told Vanity Fair. "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 said. "'You never dealt with yourself,' and I don't want that to happen."

Jenner also told People that she finally felt seen for who she really is. Holding her driver's license with her photo and the name "Caitlyn Marie Jenner" was an "emotional" experience, she revealed. Though, Jenner also admitted to wondering "what Caitlyn will do" in her new life, now that she was finally living as her authentic self.

In 2015, Caitlyn Jenner starred in her reality television show, I Am Cait, which surprised everyone. Unfortunately, the series copped a lot of criticism, as many people reportedly thought it was just another money-making stunt for the Jenner-Kardashian family. But E'!s head of programming, Jeff Olde, told Vanity Fair that the show would be anything but another Kardashian spinoff. "We all love ratings," he said. "But we understand the power and responsibility to be able to share this story."

After two seasons, I Am Cait was canceled. In a statement released to Variety, an E! spokesperson said: "We are incredibly proud of the two seasons of I Am Cait, a groundbreaking docu-series that sparked an important and unprecedented global conversation about transgender people, their struggles and triumphs." The statement also suggested that Jenner and E! had mutually decided not to move forward with another season. The show did not sustain the same audience in the second season as it did in the first — and Jenner was ready for her next adventure, she said in a tweet.

In 2017, Caitlyn Jenner published a memoir aptly titled, The Secrets of My Life, which documented her life and gender transition. "I really had no choice but to come out publicly just because the tabloids and the media were just destroying me for so long," Jenner said in an interview about the book with ABC. "I've worked over the last few years, been misunderstood, and made a lot of mistakes." 

Still, Jenner said that she tries hard to try to make a difference for her community. And while Jenner says she was true to herself and her experience in her book, the memoir wasn't so well-received by everyone. Ex-wife, Kris Jenner, for example, said that she was angry and disappointed about the book. But Jenner holds to it that her memoir is "extraordinarily honest" and from her own perspective. "When you do a book like [this], there are different opinions," she said.

In an interview with The Guardian, Caitlyn Jenner opened up about her political views, which are largely controversial within the LGBTQ+ community. Namely, in the 2016 presidential election, Jenner voted for Donald Trump because she says she believes in "limited government, lower taxes, less regulation." Many members of the LGBTQ+ community have spoken out against Jenner's vote.

The reason? Trump rolled back a rule that protected transgender people from discrimination at homeless shelters, and when applying for housing services and receiving federal funds. Additionally, in the first few months of Trump's administration, the Departments of Justice and Education withdrew landmark guidance that explained how schools must protect transgender students under the federal law (Title IX). The Trump administration also took countless other anti-transgender actions as well, according to TransEquality. 

Jenner does agree that the Republican party could do better for the trans community. "Now, do I agree with the Republicans on every issue? Absolutely not," Jenner continued. "And I know — I'm not stupid — I know that they're not as good when it comes to LGBT issues. OK? The Democrats do better there."

Despite whatever controversy she's stirred in any community, Caitlyn Jenner has no regrets. "This is my journey; yes, it is different than other trans people but, when I wake up in the morning, I'm happy with myself," she told People. 

Jenner also revealed that she doesn't regret voting for Trump, though she regularly criticizes him and his administration. She even admitted that she's even turned down golf outings with Trump because she didn't want to be seen with him. "As far as my community goes, I realize my loyalties do not lie with Donald Trump or the Republican party," she explained to The Guardian. "But I lean on that side." 

Jenner also shared that she's "not a one-issue voter," which is why she said she doesn't have regrets. "I would rather fight the Republicans to do a better job when it comes to all LGBT issues than fight the Democrats to lower taxes and give us less regulations out there for business," she added.