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

Credit: Ken McKay/ITV/Shutterstock ; Courtesy of Hulu

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

Caitlyn Jenner has had her ups and downs with the Kardashian family 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 former athlete came out as transgender. “For all intents and purposes, I am a woman,” she told Diane Sawyer during an April 2015 interview on 20/20. Caitlyn appeared on the cover of Vanity Fair in June 2015, telling the outlet that the issues in her relationship with Kris were “20 percent gender and 80 percent the way I was treated.” Khloé confronted Caitlyn over the comments during an episode of I Am Cait that aired in August 2015. “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,” Khloé said. “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." Caitlyn further discussed the past relationship when releasing her The Secrets of My Life memoir in April 2017. She claimed that Kris knew about “my gender issues,” which the Keeping Up With the Kardashians alum denied. Keep scrolling to look back at Caitlyn’s ups and downs with the Kardashian family:

Credit: Ken McKay/ITV/Shutterstock ; Courtesy of Hulu

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

Caitlyn Jenner has had her ups and downs with the Kardashian family 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 former athlete came out as transgender. “For all intents and purposes, I am a woman,” she told Diane Sawyer during an April 2015 interview on 20/20. Caitlyn appeared on the cover of Vanity Fair in June 2015, telling the outlet that the issues in her relationship with Kris were “20 percent gender and 80 percent the way I was treated.” Khloé confronted Caitlyn over the comments during an episode of I Am Cait that aired in August 2015. “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,” Khloé said. “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." Caitlyn further discussed the past relationship when releasing her The Secrets of My Life memoir in April 2017. She claimed that Kris knew about “my gender issues,” which the Keeping Up With the Kardashians alum denied. Keep scrolling to look back at Caitlyn’s ups and downs with the Kardashian family:

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1991

Caitlyn became a stepparent to the four Kardashian children when she and Kris exchanged vows. 

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2010

Caitlyn had her stepson Rob by her side when she got her ears pierced during an episode of KUWTK. The Arthur George founder even held Caitlyn’s hand as she got her new bling. 

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2011

Caitlyn stood in for the late Robert Kardashian and walked Kim down the aisle when she married Kris Humphries. The pair split just 72 days later, but Caitlyn did the honors again when the Skims mogul wed Kanye West in 2014. (Kim and West called it quits in 2021.)

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2015

Khloé called Caitlyn out for her Vanity Fair interview, in which she claimed Kris “mistreated” her during their marriage.

“We want to be there and support 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 mum through the mud,” she said during an episode of I Am Cait. 

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2016

Khloé claimed during a January appearance on the Howard Stern Show that she found out about Caitlyn’s transition at the same time as “business people.”

Noting that she felt “betrayed” by the gold medalist, the Khloé & Lamar alum said: “We felt so like, ‘What the f—k? We've been asking you and why do business people know?' … I don't give a f—k what you want to do. Just stop lying to us about things.”

During an episode of KUWTK that aired that May, Khloé claimed that her comments elicited a slew of angry text messages from Caitlyn. 

"You slaughtered my mother and you have the nerve to say, 'What happened to family sticking together?' You jumped that ship as soon as you did Diane Sawyer and attacked my mom,” she vented to Kris. “She can tell me to f—k off all she wants. I don't have a relationship with her. I'm done.”

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2017

During the season 14 premiere of KUWTK in September, Kim slammed a claim Caitlyn made in her memoir — that her late father believed his friend O.J. Simpson was guilty of murder at one point, despite defending him in the infamous 1992 trial. 

“I have always had Caitlyn’s back,” Kim said in the episode. “She is a liar. She is not a good person.” 

That November, Caitlyn opened up about her estrangement from the Kardashian clan while giving a talk at Cambridge University.

"They don't want me in their lives, they bashed me pretty badly. It's devastating when your kids do that. It really hurt,” she said at the time. “In the book I express some opinions and got shot down. It was not about the Kardashians. They were only mentioned on 20 pages. They made it more about them on television. The book was about my life. That's caused a lot of the separation between us."

Credit: Courtesy of Caitlyn Jenner/Instagram

2019

Despite past drama, Kim, Kourtney, Kendall and Kylie all celebrated Caitlyn’s 70th birthday with her in October.

“Such a special birthday dinner with family. Love you all 🥰,” the I’m a Celebrity, Get Me Out of Here! alum captioned an Instagram photo from the occasion. Khloé and Rob were missing from the picture. 

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2021

During a January appearance on “The Skinny Confidential Him & Her” podcast, Caitlyn said that she and Kendall “have a lot in common,” noting that they are both athletic and have “the same attitude towards life.”

Despite her similarities to Kendall, the politician admitted that she and Kylie “just seem to be closer most of the time.”

She continued: "Kendall's off kind of doing her thing, and Kylie, like, I had dinner last night at Kylie's house. We try to do that once a week, once every two weeks. I go over there and she always has these great meals — prepared, she doesn't do them. ... But they're so good! It's better than a restaurant."

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2023

Kim praised both of the father figures in her life in a sweet Father’s Day Instagram tribute that highlighted both her late dad and Caitlyn.

"Best to ever do it! I wouldn’t be me if it weren’t for you two,” the KKW Beauty founder captioned the carousel of photos. 

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2025

Kourtney appeared on an episode of sister Khloé’s podcast, “Khloé in Wonder Land,” in May 2025. The two recalled growing up with Caitlyn.

“[Caitlyn] never tried to be Dad and I always appreciated and respected that,” Khloé recalled, referring to her late father, Robert Kardashian. However, Kourtney disagreed.

“OK, so, that wasn’t my experience, but maybe that’s why it became your experience,” the Poosh founder added. “So [I’m] grateful for that for you.”

Kourtney recalled feeling like Caitlyn “tried to be controlling and bossy,” declaring that “certain friends” couldn’t come over to their house. “I would be like, ‘I wanna call my Dad,’ and [Caitlyn] would hang up the phone. We would have yelling wars.”

Kourntey also noted that the tension with Caitlyn led her to move in with her father, Robert.