Caitlyn Jenner reveals she originally started to transition in the 1980s but ‘had boobs removed’

Caitlyn Jenner officially came out as transgender in 2015, aged 65. However, she has revealed in a new interview that she had originally planned to transition much earlier, before she turned 40.

In a new video recorded for AOL’s Maker Conference, the controversial right-wing figure and former Olympian explained why she waited:

“Those were real dark days for me. I got a house in Malibu. I basically stayed there for six years, and I really started struggling with my identity, about ‘Who am I?'”

She added: “I tried to start doing things to make me feel better about myself. I started on hormones. My mission at that point was to transition before I was 40. Got to 39, I just couldn’t go any farther. And like three or four months later, I met Kris [Jenner]. We hit it off from day one and I was very honest with her, I had to be, I was a 36B.” Caitlyn turned 40 on October 28, 1989.

“I actually had my boobs removed”

When she decided to marry Kris, Caitlyn left hormone therapy behind, and says she had her “boobs removed.”

“Everything was really heading in the right direction and I made this decision to move on with my life, Kris and I together and this family,” she explained. “And, OK, I’ve got to get rid of these gender things and get off hormones and this and that. I actually had my boobs removed: I never told anybody that.”

Caitlyn and Kris also had an agreement about Caitlyn’s gender dysphoria. “The rules with Kris and I [were]: Don’t dress up, certainly around the house. If you really need to do that, when you’re on the road, take stuff and do that,” she revealed. “So I did that for years.”

Kris and Caitlyn had two biological children together: daughters Kendall and Kylie Jenner.

Less than a year after her split from Kris, Caitlyn came out as trans on the June 2015 cover of Vanity Fair.

Caitlyn Jenner has subsequently become a divisive figure within the LGBTQ+ community, not least because of her continuing support for Donald Trump, who is known for his anti-trans views and policies.

She was criticised for her support for Trump following his swearing-in as the 47th president.

Trump used his inauguration speech to once again attack trans and marginalised people, before signing a number of executive orders, including to remove so-called gender-ideology guidance. He declared it would become government policy “that there are only two genders, male and female.”

Despite this, Caitlyn declared was “just as happy, actually more happy, than the first time, to be celebrating the inauguration of President Trump.”

Her post was mocked by those who couldn’t believe she supported a man who, as one person put it, “literally announced that you don’t exist today.”

More recently, Caitlyn admitted that she had been negatively impacted by Trump’s trans passport policy. In November 2025, the Supreme Court allowed the Trump administration to restrict passport sex markers to male or female, and those markers had to reflect an individual’s sex at birth.

Caitlyn Jenner said in a recent interview with conservative commenter Tomi Lahren that she asked President Donald Trump for help navigating the impact of his administration’s passport policy.

She explained Trump’s policy has negatively impacted her, saying: “What do I do? This is a safety factor. I can’t travel internationally anymore. I can’t use my passport.”

She added: “I don’t blame President Trump, I love him. But for a lot of people, this is an issue.”

Jenner says she wrote a letter to Trump at Mar-a-Lago two months ago. She hasn’t heard back.

“I’m not blaming him whatsoever. I love the guy, and I love what he’s doing,” she told host Tomi Lahren.

“I haven’t heard from him. He’s kind of busy right now. My gender marker is not big on the issues, okay?”

She went on: “I’m trying to figure out now, what is the next step to try to figure this out because as we know, even to vote now you have to have proper identification. I don’t have that.”