The Most Controversial Decisions The Kardashians Have Ever Made

There are few celebrity families who manage to stay in the spotlight quite as deftly as the Kardashian-Jenner crew does — and it's not always thanks to their fans who love them. Given that many would credit Kim Kardashian's 2002 sex tape scandal for the family's rise to fame, it's no wonder that they've found themselves in the middle of more than a few controversies since then. And somehow, year after year, they just keep stacking up.

We'll give them props where props are due: there's never a dull moment for anyone who's spent the last two decades keeping up with the Kardashians. But while some of their most genius decisions (like Kylie Jenner launching Kylie Cosmetics) have led to even more success for the fam as a whole, they still get backlash for their worst ideas, and it doesn't exactly help that they love to broadcast those ideas, occasionally on national television.

Here are some of the most controversial decisions the Kardashian family has ever made. We don't doubt that there are plenty more to come in the future, but hopefully, they could learn from at least a few of these.

Kim Kardashian's COVID birthday party

Thanks to the COVID-19 pandemic, people all over the world had to cancel their birthday parties, weddings, and other celebrations in 2020 in order to stay safe and help slow the spread. But instead of skipping out on a massive bash to celebrate turning 40, Kim Kardashian not only decided to party anyway, but also to share it in an Instagram post that many fans felt was tone-deaf.

"After 2 weeks of multiple health screens and asking everyone to quarantine, I surprised my closest inner circle with a trip to a private island where we could pretend things were normal just for a brief moment in time," Kim wrote in an Instagram post that would quickly turn into a viral meme all over the internet.

During an appearance on The Ellen Show, Khloe Kardashian later doubled down and defended her sister, saying, "This year is a frustrating year, I get it. I think there's so many frustrations going on for everybody. But also it's her 40th and this is something that she really wanted to do for us, it was such a nice thing."

Despite the backlash, it still wouldn't appear that the family learned their lesson since Kendall Jenner threw a Halloween/birthday party just days later that appeared to be COVID precaution-free.

Kylie Jenner and Kendall Jenner's ill-fated t-shirt launch

Back in 2017, Kendall Jenner and Kylie Jenner attempted to release a t-shirt featuring their faces superimposed over the likenesses of Tupac Shakur and the Notorious B.I.G. without getting permission first. Not only were the controversial t-shirts not well received, but the Jenners were eventually sued by a photographer who didn't license the photo of Shakur for their use. The lawsuit was later settled.

And as for Biggie? Well, the late rapper's mother, Voletta Wallace, spoke out against the designs in a post on Instagram, stating that Kendall and Kylie had never asked for his estate's permission to use the photo of her son. "The disrespect of these girls to not even reach out to me or anyone connected to the estate baffles me," Wallace wrote at the time. "I have no idea why they feel they can exploit the deaths of 2pac and my son Christopher to sell a t-shirt."

Kendall did end up issuing an apology via Twitter, writing, "These designs were not well thought out and we deeply apologize to anyone that has been upset and/or offended, especially to the families of the artists. We are huge fans of their music and it was not our intention to disrespect these cultural icons in [sic] anyway. The tee shirts have been pulled from retail and all images have been removed."

Khloe Kardashian's choice to stay with Tristan Thompson

Though many a Kardashian relationship has received a side-eye from fans, the one that may have garnered the most disapproval was Khloe Kardashian's choice to stay with Tristan Thompson through multiple cheating scandals. It all started in April 2018, when Kardashian was just days from giving birth to their daughter, True. The Shade Room shared footage of Thompson entering a hotel with an unidentified brunette woman, and although Kardashian made it clear on Keeping Up With The Kardashians that the decision was a difficult one, she ultimately decided to stay with Thompson.

Things seemed to be going smoothly with them until it all fell apart again a year later. In February 2019, TMZ broke the news that Thompson had been seen kissing Kardashian family friend Jordyn Woods, who later appeared on Red Table Talk to say that Thompson had been the one to kiss her, and nothing more had happened.

Still, this appeared to be the final straw for Kardashian, but as the months continued, their co-parenting relationship appeared to become closer and closer to a romantic one. In the fall of 2020, sources claimed to ET that Kardashian and Thompson were together again, though, at the time of this writing, Kardashian has yet to confirm this herself.

Kanye West's run for presidency

During the already contentious presidential race involving Joe Biden and Donald Trump in 2020, in July, Kanye West officially announced his candidacy on Twitter. That being said, at that point, so many deadlines had already passed that West only appeared on 11 states' ballots, according to ABC News, which certainly made his campaign an uphill battle.

As USA Today reported, several voters took issue with West running, especially when Republican operatives in different states were seen helping West get on the ballot — supposedly to assist him in hurting Biden's chances of beating Trump in the election. This definitely raised the alarm of those working hard to get Biden elected, especially after West's previous show of support towards Trump.

Ultimately, West was only able to secure 60,000 votes, according to the Associated Press (via Deadline), and he ultimately conceded defeat on Twitter, hinting that he would run for president again in 2024.

Kendall Jenner's Pepsi commercial

Though the Kardashian-Jenner family has been involved in many different ads (such as Kim Kardashian's hilariously odd Carl's Jr. commercial), Kendall Jenner's Pepsi ad is definitely one that has garnered the most backlash. In the 2017 commercial, Jenner can be seen handing a can of the soda to a police officer who was attempting to break up a protest, and seemingly, Jenner saves the day.

Given the Black Lives Matter movement and protests about police brutality that have been going on in the United States for years, many fans believed that this commercial was especially tone-deaf. At the time, CNN reported that people felt Jenner's commercial trivialized those fighting for the movement, and later, Pepsi pulled the ad from the air.

On an episode of Keeping Up With The Kardashians, Jenner tearfully apologized for her role in the commercial, saying, "The fact that I would offend other people or hurt other people was definitely not the intent."

Blac Chyna and Rob Kardashian's breakup

From the very start, Blac Chyna and Rob Kardashian's relationship was controversial, from the way it seemingly came out of nowhere to how serious the couple became so quickly. It wasn't long before Chyna and Kardashian had secured their own reality TV show on E! called Rob & Chyna, and in September 2016, the couple used the show to announce that they were expecting a baby girl.

But despite becoming parents and even getting engaged, Chyna and Kardashian's relationship went downhill in no time. In December 2016, according to Cosmopolitan, Kardashian revealed in a series of since-deleted messages on social media that Chyna had left him and had taken their daughter with him. They appeared to reconcile, but things only got worse.

Things continued to explode for them on social media, and finally, by spring 2017, they'd called it quits for good, though Kardashian and Chyna still appear to be embroiled in a legal battle. In October 2020, Page Six reported that a judge refused to dismiss the Kardashians' request to dismiss a lawsuit brought against them that claimed that they were the reason she lost her livelihood — a.k.a. Rob & Chyna. At the time of this writing, the drama continues!

Kim Kardashian's short-lived marriage to Kris Humphries

In August 2011, Kim Kardashian said her vows with NFL player Kris Humphries in a dreamy (and expensive) wedding that fans tuned in to watch on Keeping Up With the Kardashians. Unfortunately, though, it wasn't meant to last. After just 72 days of marriage, Kardashian filed for divorce, citing irreconcilable differences.

"I had hoped this marriage was forever, but sometimes things don't work out as planned," Kardashian said in a statement to People at the time. "We remain friends and wish each other the best." Though her blog has been deleted since then, she later attempted to explain why her marriage was so short in a post on the now-defunct site, according to People"I share so much of my life on a reality show, that contemplating whether to even film my wedding was a tough decision to make, and maybe it turned out to not be the smartest decision," she revealed. "I felt like I was on a fast roller coaster and couldn't get off when now I know I probably should have."

It looks like Humphries' wounds never fully healed, as in 2019, he penned an editorial for The Players' Tribune titled, "I Never Wanted to Be That Guy." As he wrote, "I met a girl who happened to be really famous, and I got married, and..... Damn ... I should have known what I was getting into." Whoops.

Kylie Jenner's lip filler controversy

As she entered adulthood, Kylie Jenner's looks transformed right in front of our very eyes — especially her lips. At first, Jenner credited her change in appearance to simply changing the way she did her makeup, but eventually, the cat was out of the bag, and she finally decided to admit to getting lip fillers to change the size and shape of her lips.

"I have temporary lip fillers, it's just an insecurity of mine, and it's what I wanted to do," Kylie admitted on an episode of Keeping Up With the Kardashians in 2015 over footage of her avoiding a question about her lip fillers. "I'm just not ready to talk to reporters about my lips yet because everyone always picks us apart."

Fortunately, launching her famous lip kits and her brand, Kylie Cosmetics, around the same time really helped her products take off, and she's become known for her makeup expertise ever since.

Lamar Odom's overdose

After Khloe Kardashian and Lamar Odom's lengthy and painful breakup, Kardashian seemed to be moving on. But then, in 2015, Odom was found unconscious at the Bunny Love Ranch brothel in Las Vegas. He was later revealed to be suffering from an overdose, and according to E!, Kardashian and her family rushed to be by his side at Sunrise Hospital.

While people later criticized Kardashian for helping Odom recover and pushing pause on their ongoing divorce, she offered up an explanation for her decisions on the Divorce Sucks with Laura Wasser podcast. "It was like two years, or like a year or two of us trying to get the divorce going and then this happened. And then we paused the divorce, not for any romantic reasons, but I wanted to be able to help take care of him, and make sure that he would be okay again," she said.

Odom and Kardashian didn't end up getting back together, but she did stay by his side while he healed.

The Taylor Swift debacle

After Kanye West so famously interrupted Taylor Swift's acceptance speech on stage at the 2009 MTV Video Music Awards, their feud seemed to improve, and it was almost like they'd become friends... but the peace didn't last for very long. There was some disagreement between Swift, West, and Kim Kardashian over his song "Famous" — according to Swift, she hadn't agreed to him calling her a "b**ch" in the song, while West insisted that she had approved the entire thing when he called her to get her permission to release it (via The New York Times).

This led to Kardashian controversially releasing audio from the song on Snapchat, which made it appear that she and West were in the right. But that didn't end up lasting forever. 

In March 2020, the full, unedited audio of the conversation leaked on the internet, and though Kardashian tried to argue that it only proved her point, it quickly became clear that Swift had been in the right all along.

Caitlyn Jenner's autobiography

Not long after Caitlyn Jenner came out as transgender, she released her autobiography, The Secrets of My Life. In the book, Caitlyn wrote that during her marriage to Kris Jenner, she had actually told her about her gender dysphoria, and seemed to blame Kris for what had gone wrong in her life (via USA Today).

Kris took a huge issue with this on Keeping Up With the Kardashians, especially since, as she said on the show, everything Caitlyn wrote about her and their marriage was allegedly false, and the contents of the book ended up causing a feud. 

"I really tried hard to improve the relationship and spend a little bit of time, thinking maybe there's something here that I'm not seeing," Kris said on an episode of the show. "I've done nothing but open up my home and my heart to a person who doesn't give a sh*t. So, I'm done ... I've never been so angry and disappointed in somebody in my whole life."

Kourtney Kardashian and Scott Disick's relationship

Kourtney Kardashian and Scott Disick's relationship seemed like one that would last forever, especially considering they share three kids together: Mason, Penelope, and Reign. But after a few false alarms, they officially broke up for good in 2015 when sources told E! that Kardashian was reportedly fed up with Disick's partying.

Though they continued to have their ups and downs (and Disick has tried to work on himself with multiple stays in rehab since then, including one in May 2020), they never got back together.

Their co-parenting relationship has definitely remained controversial, though. On Keeping Up With the Kardashians, Kardashian and Disick have remained open about the fact that they continue to spend time together and even vacation together for their children, and they certainly do seem a lot closer than most couples who made the conscious decision to call it quits — especially judging by their Instagram posts together. It's hard to say what the future holds for those two, but they will definitely continue raising eyebrows.