Caitlyn Jenner’s Ups and Downs With the Kardashian Siblings Over the Years

Caitlyn Jenner has had her ups and downs with the Kardashian clan over the years, with the drama playing out both onscreen and off.

When the Olympian wed ex-wife Kris Jenner in 1991, she gained four stepchildren: Kourtney Kardashian, Kim Kardashian, Khloé Kardashian and Rob Kardashian. The former spouses — who announced their separation in October 2013 — welcomed daughters Kendall Jenner and Kylie Jenner during their marriage. (Caitlin also shares daughter Cassandra Marino and son Burt Jenner with ex-wife Chrystie Scott and sons Brandon Jenner and Brody Jenner with ex-wife Linda Thompson.)

Shortly after Caitlyn and Kris finalized their divorce in December 2014, the decathlon star came out as transgender during an April 2015 20/20 interview. “For all intents and purposes, I am a woman,” she told Diane Sawyer at the time.

That June, Caitlyn appeared on the cover of Vanity Fair, opening up to the outlet about her transition as well as the end of her and Kris’ relationship. The New York native claimed that the problems in her marriage to Kris were “20 percent gender and 80 percent the way I was treated.”

Caitlyn said of the momager: “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.” The I Am Cait personality’s comments left her family reeling, with Khloé publicly coming to Kris’ defense.

During an episode of I Am Cait that aired in August 2015, Caitlyn asked Khloé if they could clear the air after the Revenge Body author sent her some “tough” text messages reacting to the Vanity Fair interview.

Khloé replied: “I just said, ‘We don’t care what you’re doing’. We don’t care if you want to transition. We want to support and be there for you. But we don’t think that entails you speaking negatively about my mom. In our opinion you don’t even need to mention my mom. Let’s focus on the actual cause here and not drag my mom through the mud.”

The Good American founder added that she thought Caitlyn would’ve “come from a place of more compassion, especially when you have two young daughters who are greatly affected by it.”

The Fox News contributor’s tension with the family was exacerbated by her April 2017 memoir, The Secrets of My Life, in which she claimed that Kris had known about her struggles with gender identity for a long time.

“I tell Kris about my gender issues before I make love to her,” Caitlyn wrote. “This will always be a subject of dispute between Kris and me as to how much she could intuit about my gender issues. She insists that she was taken by surprise by my ultimate transition to Caitlyn. … I told her I dressed as a woman, and she knew I did, because I did it several times in front of her after we were married.”

During an episode of Keeping Up With the Kardashians that aired later that month, Kris slammed her ex’s memoir, claiming, “Everything that she says is made up.”

Kendall, for her part, weighed in on her parents’ drama during a June 2017 episode of the E! reality series.

“I spoke to Kim about Dad’s book and heard about all the stuff she was saying in it and how a lot of it is so not true,” the model told her mom on the show. “The weird part is I don’t think it’s purposeful lying, I think she really just thinks that’s what happened … and then she goes around dissing the Kardashians, but those are the kids that you raised. If you have a problem with them, you raised them.”

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Keep scrolling for a look at Caitlyn’s ups and downs with the Kardashian siblings over the years: