The Truth About Caitlyn's Strained Relationship With The Kardashians

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When Caitlyn Jenner announced she was transitioning in her famous 2015 interview with Diane Sawyer, it seemed like her ex-wife, Kris Jenner, along with the entire Kardashian brood, was in support of the change. But between then and now, literally everything has changed.  

Not only are Caitlyn and the rest of the family not as close as they used to be, but, if you've been watching Keeping Up With the Kardashians, you know that a Caitlyn's tell-all memoir, The Secrets of My Life, was effectively a bomb lobbed directly into the middle of reality TV's most famous family. Since the book hit the stands, Caitlyn's relationship with Kris and each of the kids unravelled faster than they crank out new personally branded fragrances.

Can they ever get back to being the funny, sometimes irreverent family that America fell in love with? Here's the truth about Caitlyn's strained relationship with the Kardashians.

The shot heard round Calabasas

When Caitlyn Jenner's revelatory Vanity Fair cover hit newsstands in 2015, it wasn't the first time photos of a transitioned Caitlyn were available to the public, but it was the first time she got to speak in depth about her marriage with Kris Jenner. Unfortunately for Kris, the piece contained some unflattering details that didn't exactly thrill the Kardashian matriarch.

"I think in a lot of ways she became less tolerant of me," Caitlyn told the magazine. "Then I'd get upset and the whole relationship kind of fizzled. 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."

Understandably, Kris was upset with Caitlyn's arguably shady assessment of their union. She described her feelings about how Caitlyn ended their marriage before disclosing her "gender dysphoria" as "the most passive-aggressive thing I think I've ever experienced." On a later episode of Keeping Up With The Kardashians (via Digital Spy), Kris really lowered the boom on Caitlyn while discussing the Vanity Fair piece when she said, "He can go f**k himself. I honestly wish I never met this man."

That high-profile airing of grievances seemed to drive the first wedge between Caitlyn and Kris and the kids, and would prove to be just the beginning of an ugly Jenner-Kardashian family feud that played out over the next few years in the tabloids, talk show interviews, and episodes of Keeping Up With the Kardashians.

Confronting Caitlyn

On the first season of Caitlyn Jenner's reality series I Am Cait, Kim Kardashian called Caitlyn out on changes she did not find flattering since her former stepparent transitioned. Kim made it clear she did not approve of Caitlyn criticizing Kris Jenner in Vanity Fair and also accused Caitlyn of distancing herself from the rest of the family.

In an episode recap by People, Kim pointed out that Caitlyn had called daughters Kendall and Kylie Jenner a "distraction" and had been spending all her time with her new friends in the trans community, letting her family relationships fall by the wayside. "You look amazing, it's your time, but you don't have to bash us on your way up," Kim said. "You've got the fame, but you're losing your family."

Kris Jenner and Khloé Kardashian also confronted Caitlyn on the show as well. "You're sensitive and amazing to all these new people in your life, you're just not so sensitive and amazing to the family that you left behind," Kris said, according to Entertainment Tonight. "We want to support you and be there for you, but, we don't think that that entails you speaking negatively about my mom," Khloé added. "I would think you would come from a place of more compassion, especially when you have two young daughters who are greatly affected by it." Shots. Fired.

Kris and Caitlyn Jenner did try to play nice for a while

The immediate aftermath of Caitlyn Jenner's transition saw the dynamic between her and Kris Jenner turn decidedly negative, although there were a few instances where they tried to at least be civil. In a breakdown of their falling out, ET cited at least two occasions where Kris and Caitlyn came together for what seemed like the sake of their kids.

In November 2015, Caitlyn and Kris appeared together at the Victoria's Secret Fashion Show in support of Kendall's first walk down fashion's most famous catwalk. According to witnesses, the exes seemed happy to see each other, and even took the time for "a whole photo op in the first row." One year later, they were still on decent enough terms for Caitlyn to land an invite to Kris' annual, star-studded Christmas Eve party.  

But it wouldn't take long for reality TV's former First Couple to once again be at each other's throats when, just four months later, Caitlyn dropped her memoir, The Secrets of My Life. After that, nothing was going back to the way it was ever again.

20 pages to destroyed Caitlyn Jenner's relationship with the Kardashians

Though Caitlyn Jenner's book, The Secrets of My Life, only dedicates 20 pages to the Kardashians — as Caitlyn would later claim in her defense — there was enough dirt in it to potentially fracture this once tight-knit family forever. In fact, after reading the damning memoir, in which Caitlyn suggests Kris Jenner knew all about her desire to transition, both Kim Kardashian and Kris unleashed fury on Caitlyn, making it clear that a line had most definitely been crossed.

Kim took umbrage with just about every claim Caitlyn made about Kris in the book, like the assertion that Kris domineered the family finances and that making a reality show about the family was Caitlyn's idea. However, what seemed upset Kim the most was the assertion Caitlyn made regarding Kim's late father, Robert Kardashian. Supposedly Robert admitted he knew O.J. Simpson was guilty but represented him anyway "to get back at his remarried ex."

In response, Kim said on an episode of KUWTK (via the Daily Mail), "My relationship with Caitlyn ... was strained, and I was just trying to just be respectful, but if you talk about my dad, I will cut you." She added, "I've always had Caitlyn's back, but she's a liar and not a good person."

Caitlyn's memoir evoked a similar response from Kris, who initially reacted on the show (via ET) by implying that it was the last straw with Caitlyn. "None of it makes sense," Kris said, adding, "Everything she says is all made up." Unfortunately for Caitlyn, the icy dynamic put in place by the momager matriarch was quickly adopted by the rest of the Kardashian crew.

The kold shoulder

Though the Kardashian women were exceptionally vocal about Caitlyn Jenner after her memoir came out — the topic was featured prominently in the 13th and 14th seasons of the KUWTK — the chatter apparently ended as soon as the cameras shut off. In fact, for as much shade as Khloé Kardashian, Kourtney Kardashian, and, especially, Kim Kardashian have thrown at Caitlyn, there certainly hasn't been much face-to-face time between them since the aforementioned 2015 confrontation over the Vanity Fair article.

Caitlyn confirmed just how distant she'd grown from her eldest former stepdaughter during a speaking event at Cambridge Union in November 2017. "To be honest I don't talk to them anymore," she said. "Kim I haven't talked to in a year."

And as far as Caitlyn is concerned, the distance between her and the Kardashian daughters is all one-sided. "In the book I express some opinions and got shut down. ... They made it more about them on television," Caitlyn also said at Cambridge Union, adding, "That's caused a lot of the separation between us."  

The only holdouts from the Kardashian crew who maintained some semblance of a relationship with Caitlyn at that time were her biological daughters, Kylie and Kendall Jenner. However, according to E! News, as of April 2018, even Caitlyn's relationship with Kendall was feeling "very strained." 

Khloé was Team Kris from the jump

On the season 12 premiere of Keeping Up With the Kardashians (via Cosmopolitan), Khloé Kardashian and Caitlyn Jenner were not on good terms. The reason? Khloé did an interview with radio shock jock Howard Stern to promote her since-canceled show, Kocktails With Khloé. During the radio program, Khloé discussed the way Caitlyn's transition had affected her, saying she "felt betrayed" by Caitlyn because "business people knew" she was transitioning before their family.

After the radio segment, Khloé reportedly received angry text messages from Caitlyn, which prompted Khloé to phone her mom to unleash an expletive-laden rant about her former stepparent. "She can tell me to f**k off all she wants. I don't have a relationship with her," Khloé told Kris, adding, "I'm done."

Khloé and Caitlyn's relationship showed brief signs of reconciliation — although at this point Caitlyn was publicly claiming the two hadn't spoken in "like, two years" — during an April 2017 episode of KUWTK, when Khloé admitted that she missed having her stepfather in her life. Khloé even said, "I don't think Caitlyn is a bad person at all."

But by October 2017, things went sour again, as Khloé dropped any and all pretense of a reunion during a discussion about her relationship with Caitlyn on the show, saying, "I'm not talking to you because you're a bad, mean person."

Kourtney and Rob are minor players, but are definitely Team Kris

Aside from his initial support of Caitlyn Jenner's transition, Rob Kardashian hasn't spoken out much about his former stepfather other than to say, "As long as Caitlyn is happy, I'm happy," during a September 2016 interview with People. But once again, it was Caitlyn who offered the truth about her strained relationship with Rob when she told the panel at The View in July 2017, "Rob, I haven't had a serious conversation with in years" (via ET).

Kourtney Kardashian, in her typically deadpan way, also aligned herself with her mom and sisters when she said on a season 14 episode of KUWTK (via the Daily Mail) that Caitlyn's "personality just doesn't vibe with ours."

She also went to bat for her mom, refuting a specific claim in Caitlyn's memoir that Kris hoarded all of the money they made from a successful motivational speaking business they ran in the '90s. "They made the money together," Kourtney said. "Even when mom would book appearances, I worked for her, I would hear her phone calls in the office. She would hustle to get speeches."

This whole ugly scenario surrounding Caitlyn's memoir proved that if there's one thing the Kardashians do better than branding, it's circling the wagons. And, unfortunately for Caitlyn, she kept on giving them reasons to keep her on the outside.

Caitlyn admitted she no longer trusts the Kardashians

One of the big moments from the season 14 premiere of KUWTK was when the family found out about Caitlyn Jenner's gender reassignment surgery in the press. Though they'd all long since cut ties with her at this point, it still somehow came as a shock to Kim Kardashian, Khloé Kardashian, and Kourtney Kardashian that Caitlyn hadn't directly told them about it.

"So that means they snipped?" Kourtney asked. "Yeah they snipped. But why couldn't she say that to us?" Kim replied, according to the Daily Mail. Aside from the obvious answer that that would be a pretty awkward icebreaker phone call to make after a few years of silence, Caitlyn actually addressed this publicly.

In a January 2018 interview with Piers Morgan, Caitlyn revealed that she hadn't told any of the Kardashians about her surgery because "it's none of their business." Asked by Morgan why she withheld the section about it in her book from the advanced copies she gave the Kardashians, Caitlyn said, "I didn't want them to leak it to the press. ... Of course I didn't trust them."

Granted, Caitlyn drifted pretty far from the family in the wake of her split from Kris in 2013, but to say that she no longer trusted them spoke volumes about the state of their strained relationship at the time.

Kris and Caitlyn Jenner hit a stalemate

In case Caitlyn Jenner telling Piers Morgan that she doesn't trust the Kardashians wasn't enough of an indicator of the family's then-fractured status, Kim Kardashian had also already put a fine point on the matter during a May 2017 appearance on Watch What Happens Live. Basically, at this point it time, there was little chance of a resolution between the two matriarchs.

During the appearance, host Andy Cohen asked Kim, "What are the chances of your mom, Kris, and Caitlyn ever speaking again?" Kim started to reply with, "Zero," but corrected herself and said, "One. No, I would say two. Two percent and those are Kendall and Kylie. ... All fair, I think." Yeesh.

It appeared that Kris and Caitlyn were at a stalemate. The wounds opened by Caitlyn's memoir were still fresh in a December 2017 episode of KUTWK, where Kris was clearly still defensive about claims that she knew about Caitlyn being transgender throughout their marriage (via Us Weekly).

"I wouldn't have seen that truth in, like, a gazillion years," Kris said, referencing the "perfect years" of her marriage to Caitlyn which may have blinded her to what was really going on. She also offered a final thought on Caitlyn's revelations about their marriage, saying she wished she would have only written, "Married to her. Didn't work out. She's a great girl." Unfortunately, that toothpaste is out of the tube.

Do Kris and Caitlyn Jenner have an unlikely truce?

Despite the shock of Caitlyn Jenner's memoir, it seems like she's managed to mend her relationship with her ex-wife. In November 2019, the I'm a Celebrity ... Get Me Out of Here! star shared an Instagram tribute, calling Kris Jenner a "special woman" in celebration of the star's 64th birthday. "What an amazing mother and business woman you are. Love you," Caitlyn wrote alongside a photo of the pair smiling.

What's more meaningful than a simple birthday tribute is the fact that Caitlyn defended Kris — and the whole lot of the Kardashians — to her mother, Esther Jenner, later that month. According to Us Weekly, Esther went on-record with the Daily Mailsaying that KUWTK had "no plot" and that Kris made Caitlyn "look unassertive and spineless." Caitlyn shut it down ASAP.

"Caitlyn's team adamantly denies her mother's statements as they do not represent Caitlyn's sentiments or feelings towards the show or Kris Jenner," a representative for the star told Us Weekly. "Caitlyn has time and time again said that the show is the best thing that has happened to their family, and is on great terms with Kris."

So there you have it: one Kardashian-Jenner is powerful enough on their own, but as a solid unit, they're unstoppable.

Caitlyn Jenner and Kim Kardashian are on great terms

Kris Jenner wasn't the only one to work things out with Caitlyn Jenner following the release of her shocking memoir. Kim Kardashian also managed to maintain a strong relationship with her former stepfather, but it was muddied up because of a miscommunication during Caitlyn's transition. During a live Q&A in early 2020 (via Metro), Caitlyn revealed that Kim was the first of the Kardashians to learn about her transition, but only because she "kind of caught" the star, so Caitlyn told her first.

"I talked to her and I felt so good after it was over, and she was just great, she was fine," Caitlyn said (via Metro), "But then for the next nine months, she never brought the subject up again. And for those nine months, I thought, 'Oh my God, was she upset about that?'"

After nine months, Caitlyn finally brought it up to Kim once again, and Kim admitted that she just wasn't sure "how to deal with it." She didn't know if it was okay to talk about because Caitlyn wasn't talking about it. "I saw where she was coming from, and everything's fine now. We have a great relationship today," Caitlyn said (via Metro).

Is Khloe Kardashian still holding onto her grudge?

It seems like Khloe is still the one Kardashian holding onto her grudge with Caitlyn. During a November 2019 episode of I'm a Celebrity ... Get Me Out of Here!, the former Olympian revealed to her castmates that Khloe had the most difficulty with her transition and things haven't sorted themselves out. The pair haven't spoken in half a decade.

"Khloe, for some reason, was pissed off about something through this whole process," Caitlyn said. "Honestly, it's been five, six years and I really haven't talked to her since."

The hostility was a devastating blow for Caitlyn, who felt particularly close to Khloe because she raised her since she was five years old. The month prior to the interview, Khloe had been the sole Kardashian sister to skip out on her former stepdad's 70th birthday party, according to TMZ. She was reportedly busy filming a commercial, so there might not have been any actual shade there. Maybe there's hope for them yet.

Can the trust ever be rebuilt?

Despite Kris and Caitlyn Jenner's seemingly tenuous reconciliation, it doesn't look like the trust has been built all the way back up. According to a source that spoke to The Sun, Kris was "scared and horrified" when Caitlyn signed on for the British reality series I'm a Celebrity ... Get Me Out of Here! because she feared the Olympian would divulge damaging secrets about their daughters' lives. This report came around the same time that Caitlyn was repping her ex-wife on Instagram, so how good was their relationship, really?

According to the source, Kris was concerned that part of Caitlyn's "massive fee" to appear on the series might have to do with spilling family secrets. While she didn't care about her ex divulging details about their marriage (the ship kind of sailed with that one after the memoir), she was reportedly concerned that any tea-spilling by Caitlyn could be "damaging to "Kim and Kylie's brands." The source continued, "Before Caitlyn left for Australia, she wished her good luck — and let her know she'd be watching to see what she says."

It seems like Kris' worries were just that: worries. When Caitlyn got voted off the series in December 2019, Kendall and Kylie surprised her with a big welcome home, according to People, so it doesn't seem like anyone in that camp is mad about her stint on the show.