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.

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."

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.

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!

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.

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.

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.