Caitlyn Jenner's Most Controversial Moments

Caitlyn Jenner is an Olympic gold medalist, an author, a public speaker, a reality television personality, a political candidate, a trailblazing representation of trans women in media ... and one of the most controversial figures in the public sphere. She won a gold medal at the 1976 Olympics and inspired a generation by appearing on a Wheaties box, but as Jenner recalled in an episode of the Netflix docuseries "Untold," "I was an Olympic champion, greatest athlete in the world ... but I was still the same old person, with all the same old issues." Jenner struggled with her gender identity, even as she skyrocketed to higher levels of superstardom on "Keeping Up with the Kardashians" while trying to suppress the fact that she knew she was different.

She came out in 2015 amid a firestorm of speculation about her identity, finally admitting to the world that she was trans. A Vanity Fair cover — featuring an instantly iconic photo shot by Annie Liebovitz — announced her new name to the world: "Call me Caitlyn." In a behind-the-scenes video, she said, "Caitlyn doesn't have any secrets. Soon as the 'Vanity Fair' cover comes out, I'm free."

However, that new freedom came with a level of public scrutiny like never before. Her well-documented conservative values have often been at odds with the kind of trans icon people expected her to be, and she's repeatedly caused controversy because of it. These are Caitlyn Jenner's most controversial moments.

Early in Caitlyn Jenner's public life as a trans woman, she upset trans advocates with her remarks about the ability of certain trans people to "pass" — that is, to move through society undetected as "trans." That's impossible for many trans individuals, especially those without access to the same resources Jenner had, not to mention every trans person might not want to pass. As writer Emily VanDerWerff put it, "As trans people, we're supposed to complicate the gender binary, not uphold it. By trying my damnedest not to stand out but to blend in ... I'm propagating a system that hurts both trans people and women disproportionately."

And yet, Jenner told Time upon her inclusion on their "Person of the Year" shortlist that she worked on her "presentation" specifically to put others at ease. The remarks were removed from the interview after they caused controversy, but Cosmopolitan preserved them. "I think it's much easier for a trans woman or a trans man who authentically kind of looks and plays the role," she said. "If you're out there and, to be honest with you, if you look like a man in a dress, it makes people uncomfortable."

After pushback, she apologized in a since-deleted blog post titled "I Have So Much To Learn." She clarified (via ET), "People who look 'visibly transgender' sometimes can struggle for acceptance and may be treated poorly by others. And while this may be true, it's also something that needs to change."

In the early days of her first public appearances as Caitlyn Jenner, she made numerous allowances for people to use her wrong pronouns and name. It is, of course, her right to allow people to use the wrong pronouns and her deadname, but as Vox notes, she is the highest-profile trans woman in the country, so her allowance could be construed as permission for other people to act that way with less-powerful trans people, which can be incredibly harmful and triggering (via Healthline).

For example, in the Vanity Fair article introducing Jenner to the world, writer Buzz Bissinger repeatedly referred to her deadname and openly admitted to having used the wrong pronouns multiple times, even going so far as to call her "dude" and "man." Instead of using the opportunity to educate him, however, Jenner told Bissinger, "I don't really get hung up" on pronouns and her deadname, actions which can significantly negatively affect the trans community, due to her visibility. 

Jenner has continued to experience widespread misgendering and deadnaming since coming out, perhaps in some part because of her early allowances. The transphobia has come from comedians, newscasters, and critics, including everyone from trolls on Twitter to "Weekend Update" host Michael Che on "SNL" (via People). "When large platforms like SNL deadname and misgender trans people it legitimizes the notion of trans-ness as spectacle and fraud," tweeted ACLU lawyer Chase Strangio. "It isn't funny. It is dangerous."

Republicans often try to limit trans individuals' rights, and Senator Ted Cruz of Texas is no different. In reference to bathrooms, Cruz told controversial YouTuber Stephen Crowder, "The idea that the federal government is coming in saying that boys, with all the God-given equipment of boys, can be in the shower room with junior high girls ... this is lunacy."

However, in 2016, Caitlyn Jenner told The Advocate that she liked then-presidential candidate Cruz, despite his views on trans individuals. "I think he's very conservative and a great constitutionalist and a very articulate man. I haven't endorsed him or anything like that," she said. "But I also think, he's an evangelical Christian, and probably one of the worst ones when it comes to trans issues." When asked why she liked him if that was the case, she said she'd love to be a "trans ambassador" in his administration.

That offer did not go over well in the LGBTQ+ community, given Senator Cruz's repeated homophobic remarks. Openly gay tennis icon Martina Navratilova tweeted, "Cait – you really must be joking about Cruz, right? Tell me it ain't so..." Jenner responded, telling E! News, "I never said that I endorsed Ted Cruz. I said I like him. He is a constitutionalist and I think we have to get our country back to something like that." As Cruz lost the election, Jenner never had the chance to make good on her offer.

During a controversial interview with Ellen Degeneres, Caitlyn Jenner was asked about her previous lack of support for gay marriage. Jenner said she had moved away from her original position, like many over the past few decades. She said she ultimately decided, "if that word 'marriage' is really, really that important to you ... I can go with it, you know?" Degeneres pointed out that Jenner still seemed hesitant about supporting marriage equality wholeheartedly, noting that the word "marriage" is indeed important because "marriage is marriage and equality is equality."

After the interview, Jenner was upset that she'd been asked the question. Years later, she told her "Big Brother VIP Australia" castmates, "Looking back on it I could have handled a couple of things a little bit differently." However, she said Degeneres then went to the media and lied about her answer, and "absolutely burned my a**." She even said she considered banning any of the Kardashian-Jenner clan from appearing on "The Ellen Show" as a result of how she was treated, though ultimately she didn't choose to pursue that line of thinking.

Caitlyn Jenner was the subject of a reality show called "I Am Cait," an opportunity for her to explore her identity. She surrounded herself with trans advocates in an attempt to learn about the community she was now openly a part of; however, she often clashed with the trans people on her show. She refused to learn or grow, sticking closely to the conservative views she held before she transitioned.

In the Season 2 premiere, she told the camera (via People), "[They think:] 'You can't be conservative anymore. You have to be a liberal.' No, I don't believe that. I think I can keep all of my views the same cause I feel in my heart that's the best way to go." Cast member Jenny Boylan, a writer and advocate, asked Jenner to look into how Republican policies hurt the trans community, but Jenner refused. "You need to look at it," Boylan said, adding later, "I hope you will recognize you're a leader." In response to being told that maybe her views were harmful, Jenner responded, "Oh, please."

Jenner announced the show's cancellation on Twitter after its second season, writing, "Thank you E! & thank you to the best girlfriends I could ask for!" Many of the women on the show, including actress Jen Richards, have since disavowed Jenner. "I think I've kind of given up on her," Richards told People amid Jenner's later run for California governor.

Fans of "Keeping Up with the Kardashians" know that Caitlyn Jenner is still close with her daughters Kylie and Kendall, but her relationship with her three sons seems strained. When she decided to run for governor, TMZ reported that she had only called her sons to let them know the night before she went public with her announcement. According to the outlet, they advised her against going ahead with the campaign, and TMZ cited sources that claimed Brody, Burt, and Brandon Jenner felt their mother was unqualified to be a politician because she didn't have any political experience.

The Jenner boys have spoken in the past about their difficult relationship with Caitlyn. Brandon wrote that she was mostly absent from his life, explaining in an essay (via News.com.au), "Sadly the infrequent exchanges felt more like staged photo opportunities than real bonding. In fact, they were stage photo ops for 'family' Christmas cards."

Brody said on "The Hills: New Beginnings" that he, too, felt distant from Caitlyn, especially once "KUWTK" began. "When I was really little, we got to spend a little bit of time. When [she] started, you know, obviously with the family, the Kardashian family and all of that, I didn't really see much of [her]," he said (via ET). Of Brody's decision to talk about Caitlyn on "The Hills," a source told ET, "Caitlyn and the Kardashians have been able to have their narrative on everything, now Brody has an outlet."

It's kind of the Kardashian-Jenner way, but since her marriage to Kris Jenner ended, Caitlyn Jenner has perhaps been too open about what went wrong. In her iconic Vanity Fair article, she said of her former wife, "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." Kris, however, felt the source of conflict was reversed, responding, "[She] was married to me and [she] wasn't who [she] wanted to be so [she] was miserable ... All I was doing was working very hard for my family so that we could all have a wonderful future, and [she] was pissed off."

Later, after the release of her memoir "The Secrets of my Life," Caitlyn sparked backlash from her family by being so forthcoming. In the book, she claimed to have told Kris about her struggle with her gender, which Kris denies. Caitlyn wrote they would likely always argue about who knew what when. "She insists that she was taken by surprise by my ultimate transition to Caitlyn ... I told her there had been a woman inside me all my life."

On "Keeping Up with the Kardashians," Kris expressed shock over the book. "None of it makes sense ... everything she says is all made up," she told an incredulous Kim Kardashian. "Why does everything have to be that 'Kris is such a b***h and a**hole?'"

In 2015, Caitlyn Jenner rear-ended a woman named Kim Howe while driving, sending her car into oncoming traffic. The victim's car was then hit by another car, and she was killed at the scene. Jenner released a statement at the time to E! News, writing, "It is a devastating tragedy, and I cannot pretend to imagine what this family is going through at this time. I am praying for them." According to the Los Angeles County Sheriff's Department (via Billboard), Jenner was found to have been traveling at speeds "unsafe for the prevailing road conditions."

However, CNN reported that Jenner was ultimately not charged with anything after the crash. An investigator explained they had examined Jenner's apparent braking time and had determined, "Based on facts, [they] cannot prove beyond a reasonable doubt that suspect's conduct was unreasonable." However, according to the LA Times, a lawsuit from the victim's family was settled by Jenner for an undisclosed amount of money.

The family of the survivors of the crash, on the other hand, told The Daily Beast they were considering voting for Jenner in the California gubernatorial election anyway, even though their family had been "changed forever" by what had happened. The outlet pointed to photos posted on Facebook in December 2020, showing the couple attending an event hosted by a conservative group at Donald Trump's Mar-a-Lago resort.

Despite having no political experience, Caitlyn Jenner threw her hat in the ring for the governorship of California, evidently believing she deserved to lead the state as a prominent Republican. Jenner supported the recall of Governor Gavin Newsom, insisting he went too far in trying to protect Californians from the effects of the COVID-19 pandemic.

In the announcement of her candidacy, Jenner conflated her experience racing the decathlon in the Olympics with the stamina it would take to win a political race. "Taking on entrenched Sacramento politicians and the special interests that fund them requires a fighter who isn't afraid to do what is right," she wrote. "I am a proven winner and the only outsider who can put an end to Gavin Newsom's disastrous time as governor."

Her candidacy was not well-received, however. Vox noted that people in the LGBTQ+ community dreaded the inevitable transphobia that would occur in the media coverage surrounding her run, and indeed, San Francisco Republican Party Chairman John Dennis used Jenner's deadname in an interview with KTVU, even as he supported her. Her campaign would be marred by numerous controversies — see below — and Jenner would ultimately fail spectacularly, receiving only slightly more than 1% of the vote. She told reporters (via People) that she was surprised by the outcome of the recall, which saw Governor Newsom retain his seat. "I can't believe that this many people actually voted to keep [Newsom] in office," she said.

Caitlyn Jenner received considerable backlash for voting for Donald Trump, who claimed to support the LGBTQ+ community but instituted numerous policies to make their lives more difficult, including banning trans people from serving in the military. Jenner told Seth Meyers that she was "not a one-issue voter" and that she prioritized "the Constitution" and "freedom" over "equality." However, she noted, "I gotta keep an eye on these people."

In 2018, she wrote an op-ed for The Washington Post admitting, "I was wrong." She listed off a number of Trump's offenses, writing, "He has ignored our humanity. He has insulted our dignity. He has made trans people into political pawns as he whips up animus against us in an attempt to energize the most right-wing segment of his party." She concluded, "This is politics at its worst. It is unacceptable, it is upsetting, and it has deeply, personally hurt me."

However, when she ran for governor and needed his supporters on her side, Jenner was back to talking up Trump. She told Sean Hannity (via The Hill) that she liked Trump because he was "a disruptor," though she allowed, "He did some things that I agree with, some things I didn't agree with." Though she claims she didn't vote for him in 2020, she also didn't vote at all, telling CNN she played golf instead. And on Fox News, she said she'd support him again in 2024, directly contradicting her "I was wrong" statement. 

When Caitlyn Jenner first came out as trans, she received the Arthur Ashe Courage Award at the ESPYs. In her acceptance speech, she advocated for the right of trans youth to play sports that correspond to their identity, telling the crowd, "I also want to acknowledge all the young trans athletes who are out there, given the chance to play sports as who they really are."

A few years later, though, during the California gubernatorial election, TMZ caught up with the former Olympian and asked her about the public debate over whether trans girls should be allowed to play on girls' teams. This time, Jenner said, "This is a question of fairness. That's why I oppose biological boys who are trans competing in girls' sports in school. It just isn't fair, and we have to protect girls' sports in our schools." Soccer star Ali Krieger, an out lesbian, told Variety she was surprised by the answer. "I feel like every kid, including trans kids, should have the opportunity to play the sport they love to play," Krieger said.

Jenner's stance evolved further a few weeks later, and she made a proposal seemingly at odds with the conservative principle of small government. Discussing the controversy on "America's Newsroom" (via Newsweek), she said she would prefer the state to set up a "review board" to determine who is "truly trans," preventing participation by "some guy who hasn't done any therapy."

During the California gubernatorial race, Caitlyn Jenner put forward what many viewed as an odd proposal for how to address the homelessness problem in Los Angeles. For the record, LAist reported around the time of Jenner's run for Governor in 2021 that there were more than 63,000 people without homes in Los Angeles County. Rather than actually solving the issue, however, Jenner instead suggested that people without homes should all be moved to open fields, evidently believing this would be the best way to prevent their presence from sullying the image of local businesses. After pointing out that Venice Beach has seen a rise in people experiencing homelessness over the past few years, Jenner told KRON that their presence was causing issues for local businesses, insisting, "We have to clean those places up." She then offered her solution: "We have to provide some place for those people to go, whether it's an open field out in some place, or if you notice at the veteran's facility, there's these big open fields and a lot of places there."

The proposal ignited a firestorm of controversy online, with many people noting that Jenner is a very rich woman who could be doing more to solve the problem rather than just pushing it out of sight. New Jersey gubernatorial candidate Lisa McCormick called the bizarre suggestion "political cowardice & inhumane disconcern" on Twitter, noting that Jenner's net worth was over $100 million.

In 2021, in the middle of Caitlyn Jenner's campaign to replace California Governor Gavin Newsom, she flew to Australia, which meant she needed to be granted an exemption for the country's notoriously strict COVID-19 lockdown and quarantine rules. If she had been traveling overseas on official campaign-related business, that might have been one thing, but Jenner drew considerable international ire because the reason for her special treatment was not because of her attempt to be a politician. No, Jenner broke lockdown rules because she wanted to participate in the Australian version of "Celebrity Big Brother," called "Big Brother VIP."

As one might expect, the move caused a firestorm of controversy Down Under. Sky News host Paul Murray was particularly upset with the move, noting that numerous Australians were still stuck abroad more than a year into the pandemic due to the country's severe lockdown. He said (via Business Insider), "This is ridiculous. There are literally flights that are returning with zero people on them because of travel caps, but she can fly into the country."

On the very day the show's trailer and cast list were announced, Jenner revealed on Twitter that she had already been eliminated from the competition and was back in the United States, making the whole exercise feel extra-pointless. She made headlines anyway during her brief appearance on "Big Brother VIP" for telling her housemates about her former friend OJ Simpson, saying, "Obviously, he did it."

Dave Chappelle recently found himself embroiled in controversy over the transphobic comments he made in one of his Netflix stand-up specials. In "The Closer," he announced he was "team TERF" (Trans-exclusionary Radical Feminist). He also made jokes about a trans woman he claimed was a friend (via Newsweek). Amid the furor, Chappelle visited his old high school in November 2021, and the students told him he was a bigot and that rhetoric like the anti-trans diatribes in his special were responsible for the deaths of trans people. Variety reported that he responded by mocking the kids, telling them, "I'm better than all of you."

Somewhat predictably, Chappelle blamed "cancel culture" for the hubbub, and just as predictably, Caitlyn Jenner leapt to his defense. "This isn't about the LGBTQ movement," she tweeted. "It's about woke cancel culture run amok, trying to silence free speech. We must never yield or bow to those who wish to stop us from speaking our minds." Chappelle had even taken aim at Jenner in the very same special she was defending, making transphobic jokes we won't print here about her having won a Woman of the Year award from ESPN. "I'd be mad as sh*t if I was a woman," Chappelle concluded (via Us Weekly).

Like many on Twitter, writer Dani Stewart disagreed with Jenner's support. "You don't speak for me or ANY other trans folx I know," she replied. "Caitlyn, you need to soul search."

On October 28, 2022, Speaker of the House Nancy Pelosi's husband Paul Pelosi was attacked inside the couple's home by an assailant with a hammer. According to BBC News, David DePape broke into the home and shouted, "Where is Nancy?" before bludgeoning the congresswoman's husband. CNN reported that the suspect had shared conspiracy theories on social media regarding the COVID-19 pandemic and the 2020 presidential election. He will be charged with "attempted homicide, assault with a deadly weapon, elder abuse, verbal and several other additional felonies," police said.

As news was still breaking about the attack, Caitlyn Jenner appeared on Fox News to offer her opinion. "My heart and prayers goes out to the Pelosi family," she began, quickly moving on after condemning the attack. She added, "Why this home wasn't better protected is kind of beyond me. ... Seems like Pelosi needs to re-evaluate her security, especially in a violent city of San Francisco." Jenner went on to say that the attack isn't a partisan matter, and then almost immediately began talking about the dangers of "soft-on-crime liberals." Moments after cautioning against partisanship, she added, "We have to get these people out of office." So much for avoiding political spin.

"Pretty sure the partisan attacker made it a partisan issue," one Twitter user wrote as Jenner's name trended online. Another suggested, "Add victim blaming to the long list of bad takes from Caitlyn Jenner."