Caitlyn Jenner's Transformation: Navigating the Complexities of Family Dynamics with the Kardashian Siblings

Caitlyn Jenner's relationship with the Kardashian clan has had its share of ups and downs throughout the years, with the drama unfolding both on and off the screen.

After marrying ex-wife Kris Jenner in 1991, the Olympic athlete became a stepmother to four children: Kourtney, Kim, Khloé, and Rob Kardashian. During their marriage, Caitlyn and Kris also welcomed two daughters, Kendall and Kylie Jenner. It is worth noting that Caitlyn has other children from previous marriages as well, including daughter Cassandra Marino and son Burt Jenner from her marriage to Chrystie Scott, and sons Brandon Jenner and Brody Jenner from her marriage to Linda Thompson.

Shortly after Caitlyn and Kris officially ended their marriage in December 2014, Caitlyn revealed her true identity as a transgender woman during a 20/20 interview with Diane Sawyer in April 2015. She confidently stated, "I am, for all intents and purposes, a woman."

In June of the same year, Caitlyn graced the cover of Vanity Fair, sharing her journey of transitioning and discussing the complexities of her relationship with Kris. Born and raised in New York, Caitlyn candidly expressed that the issues in her marriage were primarily attributed to "20 percent gender" but mostly stemmed from the way she was treated.

Caitlyn revealed that her relationship with the momager was often unpleasant, as she experienced mistreatment and felt controlled by Kris, especially when it came to financial matters. These revelations had a profound impact on Caitlyn's family, with Khloé publicly defending Kris. In an episode of I Am Cait aired in August 2015, Caitlyn approached Khloé, seeking to resolve their issues after receiving some challenging text messages from her in response to the Vanity Fair interview.

Khloé responded, stating that she had simply expressed that they were not concerned about the actions Caitlyn was taking. Instead, their focus was on offering support and being there for her. However, Khloé believed that speaking negatively about her mother was unnecessary and detracted from the real issue at hand. She emphasized the importance of directing attention towards the actual cause rather than tarnishing her mother's reputation. Additionally, Khloé expressed her disappointment in Caitlyn for not approaching the situation with more compassion, particularly considering the impact it had on her two young daughters.

In her memoir, The Secrets of My Life, published in April 2017, the Fox News contributor revealed that Kris had been aware of her struggles with gender identity for a significant period of time. Caitlyn wrote that she had informed Kris about her gender issues before they engaged in any intimate moments. However, the extent to which Kris could understand or sense her gender struggles became a point of contention between them. Kris maintained that she was completely caught off guard by Caitlyn's decision to transition to a woman. Caitlyn countered by stating that she had dressed as a woman on multiple occasions in front of Kris after they had tied the knot, indicating that Kris was aware of her gender exploration.

Kris criticized her ex's memoir on an episode of Keeping Up With the Kardashians that was aired later that month, accusing her of fabricating everything she says. Kendall also shared her thoughts on her parents' conflict in a June 2017 episode of the E! reality series.

During the show, the model confided in her mother, sharing her conversation with Kim regarding Dad's book. She expressed her disbelief at the inaccuracies portrayed in the book, emphasizing that she believes it stems from Kim's genuine belief in those events. Furthermore, the model highlighted the irony of Kim criticizing the Kardashians, considering that they were the children her mother raised. Now, let's explore Caitlyn's journey with the Kardashian siblings, including both the highs and lows, over the years.

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Caitlyn Jenner's Ups and Downs With the Kardashian Siblings Over the Years Before and After Her Transition

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

After marrying ex-wife Kris Jenner in 1991, Caitlyn gained four stepchildren: Kourtney Kardashian, Kim Kardashian, Khloé Kardashian, and Rob Kardashian. Kendall Jenner and Kylie Jenner were also born during their marriage. Following the finalization of their divorce in December 2014, Caitlyn publicly came out as transgender in an interview with Diane Sawyer on 20/20 in April 2015, stating, "For all intents and purposes, I am a woman."

In June, Caitlyn made an appearance on the cover of Vanity Fair where she candidly discussed her transition and the end of her relationship with Kris. The New York native revealed that the issues in their marriage were primarily due to how she was treated, with only a small portion being related to gender. Caitlyn expressed that Kris often treated her poorly and had control over their finances. Her comments caused a stir within her family, leading Khloé to publicly support Kris.

During an episode of I Am Cait that aired in August 2015, Caitlyn approached Khloé with a request to resolve any lingering tension after receiving some challenging text messages from Khloé in response to the Vanity Fair interview.

Khloé's response was straightforward: “I simply expressed, ‘We don't pay attention to what you're doing'. We don't mind if you choose to transition. We want to support and stand by you. However, we believe that doesn't involve speaking negatively about my mother. In our perspective, mentioning my mother is unnecessary. Let's concentrate on the real issue at hand and refrain from tarnishing my mother's reputation."

The founder of The Good American expressed disappointment in Caitlyn's lack of compassion, particularly considering the impact it has on her two young daughters. The tension between the Fox News contributor and the family escalated further with the release of her memoir, "The Secrets of My Life," in April 2017. In the book, she revealed that Kris had been aware of her gender identity struggles for a significant period of time.

Caitlyn revealed that she had discussed her gender issues with Kris before becoming intimate with her. However, there was always a disagreement between them regarding how much Kris could understand about Caitlyn's gender struggles. Kris maintains that she was completely caught off guard by Caitlyn's decision to transition into Caitlyn. On the other hand, Caitlyn asserts that she had openly dressed as a woman in front of Kris multiple times after they got married. In a later episode of Keeping Up With the Kardashians, Kris strongly criticized Caitlyn's memoir, dismissing it as a fabrication.

During a June 2017 episode of the E! reality series, Kendall expressed her thoughts on her parents' ongoing drama. She revealed that she had a conversation with Kim regarding their father's book and was informed about the misleading claims made within it. Kendall believed that Kim's intentions were not to purposefully deceive, but rather she genuinely believed that those events had occurred. Kendall found it perplexing that Kim would criticize the Kardashians, considering they were the children her mother had raised.

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

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1991

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

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Caitlyn received support from her stepson Rob as she bravely had her ears pierced during a memorable episode of KUWTK. A heartwarming moment was captured as the founder of Arthur George held Caitlyn's hand while she adorned herself with new bling.

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2011

Caitlyn took on the role of Robert Kardashian, who was unable to attend, and escorted Kim down the aisle on her wedding day to Kris Humphries. Although their marriage ended just 72 days later, Caitlyn once again had the honor of accompanying Kim as she tied the knot with Kanye West in 2014. (Unfortunately, Kim and West decided to part ways in 2021.)

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2015

Khloé confronted Caitlyn regarding her comments about Kris in the Vanity Fair interview, expressing her disapproval of Caitlyn speaking negatively about her mother. She emphasized the importance of focusing on the actual cause rather than involving her mom in any negative discussions. This conversation took place on 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.”

During an episode of KUWTK that aired in May, Khloé expressed feeling "betrayed" by the gold medalist and shared, "We were so taken aback, wondering why we had to find out from others in the business world... I don't care about your intentions. Just be honest with us instead of deceiving." This led to a series of furious text messages from Caitlyn.

"You brutally murdered my mother and yet you have the audacity to utter the words, 'What happened to family sticking together?' You abandoned that principle the moment you engaged with Diane Sawyer and mercilessly attacked my mom," she expressed her frustration to Kris. "She can hurl insults at me all she wants. I no longer have any connection with her. I am completely finished."

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2017

In the season 14 premiere of KUWTK in September, Kim strongly criticized a statement made by Caitlyn in her memoir. Caitlyn claimed that her deceased father, despite defending O.J. Simpson in the well-known 1992 trial, believed at one point that he was guilty of murder. Kim, expressing her loyalty to Caitlyn, declared in the episode that she considered Caitlyn to be dishonest and not a good individual.

In November, Caitlyn revealed her disconnection from the Kardashian family during a speech at Cambridge University.

"They have shown no interest in having me as a part of their lives, and they have criticized me harshly. It is truly heartbreaking when your own children treat you that way. It deeply affected me," she expressed. "In my book, I shared my thoughts and experiences, but it was not primarily about the Kardashians. They were only touched upon in 20 pages. However, they chose to focus more on themselves on television. The book was intended to chronicle my life, and this has contributed to the rift 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.

“Had an incredible birthday celebration with my loved ones. Grateful for my amazing family,” wrote the former contestant of I’m a Celebrity, Get Me Out of Here!, alongside an Instagram snapshot capturing the special occasion. Notably absent from the picture were Khloé and Rob.

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2021

Caitlyn acknowledged in a recent interview on "The Skinny Confidential Him & Her" podcast that she shares many similarities with Kendall, emphasizing their athletic abilities and shared outlook on life. However, Caitlyn also confessed that she tends to have a closer bond with Kylie compared to Kendall.

She added, "Kendall is busy pursuing her own interests, while I recently had a delightful dinner at Kylie's place. We make it a point to have these get-togethers once a week or sometimes every two weeks. Whenever I visit, she always serves these amazing meals that are professionally prepared, as she doesn't cook them herself. But let me tell you, they are absolutely delectable! I would even go as far as saying they surpass the quality of a restaurant."

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2023

"Kim expressed her admiration for the father figures in her life through a heartfelt Father's Day tribute on Instagram. The carousel of photos showcased both her late father and Caitlyn, with Kim acknowledging their significant roles in shaping her identity. She affectionately stated, 'You two are the best to ever do it. I wouldn't be the person I am today without you.'"