When Caitlyn Jenner first transitioned, it seemed ex-wife Kris Jenner and their reality
TV brood were more than supportive.
But family rifts have since come to light.
Here are the details about Caitlyn Jenner's strained relationship with the Kardashians.
When Caitlyn Jenner's revelatory Vanity Fair cover hit newsstands in 2015, she finally
got to speak in depth about her marriage with Kris Jenner.
But, unfortunately for Kris, the unflattering details didn't exactly thrill the Kardashian
matriarch.
Caitlyn told the outlet,
"I think in a lot of ways she became less tolerant of me.
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 shady assessment of their union.
She described her feelings on how Caitlyn ended the marriage as the quote, "most passive-aggressive
thing I think I've ever experienced."
On an episode of Keeping Up With The Kardashians, Kris said of the Vanity Fair piece,
"He can go f--- himself.
I honestly wish I never met this man."
But that high-profile airing of grievances would prove to be just the beginning of an
increasingly ugly feud.
On the first season of Caitlyn's reality series, I Am Cait, Kim Kardashian made it clear she
didn't approve of Caitlyn criticizing her mom in Vanity Fair.
"Talk bad about my mom."
"I'm telling you."
"I come for you."
She also accused Caitlyn of distancing herself from the rest of the family, and for still
having a little of her Bruce-like edge.
"You still have a little Bruce in you.
I thought Caitlyn would be a little kinder."
"Kinder sweeter gentler."
Kim also pointed out that Caitlyn had called daughters Kendall and Kylie Jenner a quote
"distraction" in the interview, and had been spending all her time with her new friends
in the trans community.
"You look amazing.
It's your time.
But you don't have to bash us.
You've got the fame, but you're losing your family."
Kris and Khloé Kardashian also confronted Caitlyn on the show, with Kris asking her
ex for some of the same attention that Caitlyn was currently giving to her new friends.
"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."
And Khloe took a few shots on behalf of the family, saying Caitlyn should leave Kris out
of the conversation entirely, instead of dragging her through the mud, and adding,
"We want to support you and be there for you, but, we don't think that that entails you
speaking negatively about my mom."
The immediate aftermath of Caitlyn's transition saw the dynamic between her and Kris turn
decidedly negative.
But there were a few instances where they tried to at least be civil, according to Entertainment
Tonight.
In 2015, the two appeared together at the Victoria's Secret Fashion Show in support
of Kendall's first walk at the event.
And according to witnesses, the exes seemed happy to see each other, and even took the
time for a quick pic in the front 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.
"I'm getting emotional.
It makes me sad.
It does.
It makes me so sad."
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 would be the same.
"It's just…it's just the way she is."
Though Caitlyn's book only dedicates 20 pages to the Kardashians, there was still enough
dirt to potentially fracture this once tight-knit family forever.
After reading the damning memoir, in which Caitlyn suggests Kris knew all about her desire
to transition, both Kim and Kris unleashed their fury on Caitlyn.
"I have always had Caitlyn's back.
But she is a liar,"
Kim took issue with just about every claim Caitlyn made about Kris in the book, including
the assertion that Kris domineered the family finances and that doing a reality show was
all Caitlyn's idea.
But what seemed to upset Kim the most were Caitlyn's claims regarding Kim's late father,
Robert Kardashian.
Supposedly Robert admitted he knew O.J. Simpson was guilty but represented him anyway to quote,
"get back at his remarried ex."
In response, Kim said on an episode of Keeping Up,
"My relationship with Caitlyn was strained…But if you talk about my dad, I will cut you."
Caitlyn's memoir evoked a similar response from Kris, who initially reacted on the show
by implying that it was the last straw with Caitlyn.
"None of it makes sense.
Everything she says is all made up."
Unfortunately for Caitlyn, that icy dynamic was quickly adopted by the rest of the Kardashian
crew.
Though the Kardashians were exceptionally vocal about Caitlyn after her memoir came
out, the chatter apparently ended as soon as the cameras shut off.
For as much shade as Khloé, Kourtney, and Kim have thrown at Caitlyn, there certainly
hasn't been much face time between them in recent days.
Caitlyn confirmed just how distant she'd grown from the family during an event at the Cambridge
Union in 2017, claiming,
"To be honest I don't talk to them anymore.
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.
She added,
"In the book I [expressed] some opinions and got shut down…They made it more about them
on television.
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 2018, even Caitlyn's relationship with Kendall was
quote, "very strained."
"It was nothing personal."
"But you have to realize we take it personal."
On the season 12 premiere of Keeping Up, Khloé and Caitlyn weren't exactly on good terms.
And it all was because Khloé did an interview with radio shock jock Howard Stern, and revealed
her feelings of betrayal by Caitlyn because some people knew she was transitioning before
their family ever did.
Khloe said on the show,
"We felt so like, what, what the f---, we've been asking you, and why, why do business
people know, like I never want someone to feel like they have one up on our family."
After the segment, Khloé reportedly received angry texts from Caitlyn, which prompted Khloé
to call her mom, saying,
"She can tell me to f--- off all she wants.
I don't have a relationship with her.
I'm done."
Khloé and Caitlyn showed brief signs of reconciliation during an April 2017 episode of Keeping Up,
when Khloé admitted that she missed having her stepfather in her life.
"For me, you're all I remember, Bruce was.
So not having you in my life, it's a huge blow."
But by October of that year, things had gone sour again, with Khloe accusing Caitlyn of
trying to twist the situation, when the reality was something else.
She said on the show,
"Oh f--- off.
And it's not cuz of your trans, that's not why I'm not talking to you.
I'm not talking to you because you're a bad, mean person."
Aside from his initial support of Caitlyn's transition, Rob Kardashian hasn't spoken much
about his former stepfather other than to tell People magazine in 2016,
"As long as Caitlyn is happy, I'm happy."
But once again, it was Caitlyn who offered the real truth about her strained relationship
with Rob when she told The View in 2017,
"I've never met Blac Chyna, I never met the kid, Rob, I haven't really had a serious conversation
with in years."
Kourtney Kardashian also aligned herself with her mom and sisters when she said of Caitlyn
on a Season 14 episode of the show:
"It's just like…"
"Fakeness."
"...the personality just doesn't vibe with ours."
She also refuted Caitlyn's claim that Kris hoarded all of the money they made from a
successful motivational speaking business in the '90s.
Kourt claimed,
"They made the money together.
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."
"You start talking about how I was hoarding money, when we didn't even have it."
One of the big moments from the Season 14 premiere of Keeping Up was the family discovering
news of Caitlyn's gender reassignment surgery, via the press.
Though they'd long since cut ties with her, it still somehow came as a shock that Caitlyn
hadn't directly told them about it.
"So that means they snipped?"
"Yeah they snipped.
But why couldn't she say that to us?
Like, we would understand."
In a January 2018 interview with Piers Morgan, Caitlyn revealed that she hadn't told any
of the Kardashians about her surgery because it was quote "none of their business."
When asked by Morgan why Caitlyn hadn't told her own family about her transitioning, she
claimed,
"[It was] because I didn't want them to leak it to the press…Of course I didn't trust
them."
Just in case Caitlyn revealing that she didn't trust the Kardashians wasn't enough of an
indicator of the family's fractured status, Kim had already addressed the matter on Watch
What Happens Live in 2017.
"What are the chances of your mom, Kris, and Caitlyn ever speaking again?"
"Zero.
One."
"Really?"
"No, I would say two.
Two percent."
She went on to claim that the two percent had to do with Kendall and Kylie.
The wounds opened by Caitlyn's memoir were still fresh by late 2017 when Kris was defensive
about claims that she knew about Caitlyn being transgender throughout their marriage.
"Did she tell you early on?"
"No."
"Oh, I did too."
"She keeps saying she told me, but she didn't."
It appears that Caitlyn has since managed to mend her relationship with her ex-wife.
In November 2019, the star shared an Instagram tribute for Kris's birthday, writing,
"What an amazing mother and businesswoman you are.
Love you."
What's more meaningful is the fact that Caitlyn defended Kris to her mother, Esther, later
that month.
According to Us Weekly, Esther went on-record with the Daily Mail, saying that Keeping Up
With The Kardashians had quote "no plot" and that Kris made Caitlyn "look unassertive and
spineless."
Caitlyn shut it down immediately, with a rep telling Us Weekly,
"Caitlyn's team adamantly denies her mother's statements…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."
It seems like Khloe may still be holding onto her grudge with Caitlyn.
During a 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.
"Khloe, for some reason, was pissed off about something through this whole process.
Honestly, it's been five, six years, and I really haven't talked to her since."
It was a devastating blow for Caitlyn, who raised Khloe 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 step-dad's 70th birthday party, according to TMZ.
She was reportedly busy filming a commercial, so maybe there's hope for them yet.
Kim managed to salvage her relationship with Caitlyn, but it was muddied thanks to a miscommunication.
During a live Q&A in early 2020, Caitlyn revealed that Kim was the first of the Kardashians
to discover her transition, saying,
"I talked to her…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?'"
Caitlyn finally broached the topic with Kim once again, who said she didn't know if it
was okay to talk about it because Caitlyn wasn't talking about it.
Caitlyn added,
"I saw where she was coming from, and everything's fine now.
We have a great relationship today."
"It's like new year, drama free, that's like our motto this year."
Despite Kris and Caitlyn'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, quote "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?
"Kinda tryna figure out if I'm doing the right thing."
According to the source, Kris was concerned that part of Caitlyn's alleged "massive fee"
to appear on the series might have to do with spilling tightly held family secrets.
While she supposedly didn't care about her ex divulging details about their marriage,
she was reportedly concerned that any tea-spilling by Caitlyn could be quote, "damaging to Kim
and Kylie's brands."
The source added,
"Before Caitlyn left for Australia, [Kris] wished her good luck, and let her know she'd
be watching to see what she says."
It seems like Kris' worries were unfounded.
When Caitlyn got voted off the series in December 2019, Kendall and Kylie surprised her with
a big welcome home, according to People magazine, so it doesn't seem like anyone in that camp
is mad about her stint on the show.
Looks like there just might be a happy future for the Kardashian-Jenner clan yet.
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