Inside Karlie Kloss' Complicated Relationship With The Trumps

Karlie Kloss is known for many things: being a groundbreaking supermodel, a student at New York University, Taylor Swift's BFF... the list goes on. But it came as a shock to some when Kloss went public with her romantic relationship with Josh Kushner — yes, from that Kushner family. The two got engaged in 2018, after having been together for years, as noted by Harper's Bazaar, but given the political times and the association the name Kushner has with the White House, their relationship seemed to come out of left field.

So who is Josh Kushner? He's the younger brother of Jared Kushner, who, as we know, is married to Ivanka Trump. So yes, basically, the former Victoria Secret supermodel has the Trumps as in-laws and, as such, has a pretty complicated relationship with them.

Kloss, for the most part, has done her best to keep her marriage private and has refrained from talking about her dynamic with the Trumps and the Kushners on many occasions. But as with most familial dynamics, details have fallen through the cracks, and we've been able to put together a pretty clear picture of the situation. So wonder no more because we're taking a look inside Karlie Kloss' complicated relationship with the Trumps.

In the era before politics divided the brothers, Jared and Josh Kushner went into business together. As noted by The New York Times, Jared and Josh founded Cadre — a real estate start-up company — with Ryan Williams, Josh's friend from his Harvard days (casual, we know), in 2014. Cadre grew fairly quickly and, as of 2020, has some pretty significant financial partners including Mark Cuban and George Soros (who are both very prominent Democrats, by the way), Goldman Sachs, and the Ford Foundation. 

The business was back in the news in March 2020, when it was reported that Jared was selling his stake in the company, and by doing so, he afforded himself some federal deals. As reported by The New York Times, "In selling his stake, Mr. Kushner ... took advantage of a special federal program that would allow him to defer paying income taxes on any gain on his investment in Cadre." He also took advantage of the special tax break that his father-in-law signed into law in 2017. Politics can get complicated for any family, but we definitely don't envy Karlie and Josh in this situation.

Think back to 2012. SnapChat was all the rage, everything had mustaches on them (that was a weird one), everyone owned too many mason jars, and "Call Me Maybe" by Carly Rae Jepsen was on the radio. It was also the year that Karlie Kloss, one of a few supermodels who accidentally found fame, and Josh Kushner met, and as she describes it, it was like a completely different era. 

"I met my man in 2012, when I was 19 years old," she said on Watch What Happens Live. "It was 2012, it was a different world, and my man and I have been through a lot together." And given that the Kushners were prominent Democratic donors and Donald Trump himself had been a registered Democrat at one point, it's no wonder the Kloss and Kushner were more comfortable in their extended family's politics. 

But as noted by Forbes, much of the world that Kloss and Kushner knew was upended when Donald Trump came onto the political scene as a contender. "Press and paparazzi gobbled up everything Kushner, family demons included," Forbes reported about the situation the couple were in, especially about Josh's business interests. "Josh found himself linked, at least in perception, to proposals most of the tech community abhors."

It's no secret that in-laws can become the best of friends — a brother-in-law can go from your sibling's spouse to your closest companion in a matter of days. And it seems like that was the case for Josh Kushner. Jared Kushner and Ivanka Trump met in 2007, five years before Josh met Karlie Kloss, and Josh and Ivanka hit it off (in a very platonic way). As noted by Bustle, Ivanka and Jared got engaged in 2008 and married in 2009 — and like any good sibling, Josh was there to witness their love story unfold. 

When Josh appeared on the cover of Forbes in 2017, the dynamic of his relationship with Ivanka was revealed — Ivanka is "a woman so close to Josh that he calls her his sister rather than his sister-in-law," the magazine reported, and honestly, that's a crazy dynamic to envision given the politics of it all. Despite any drama, Jared and Ivanka were there when Josh and Kloss got married. As noted by Bustle, Ivanka and Jared were among the 80 guests at the wedding, and Ivanka even shared her support for the couple on social media.

Things must have gotten really awkward when the Trumps and Jared Kushner found out that Karlie Kloss voted for Democratic presidential nominee Hillary Clinton in 2016. She made it very clear on her Instagram account (that is followed by a rich 8.9 million people) that she did not vote for Donald Trump, who would one day become her extended family. When she took to social media in 2016 and posted a picture of herself voting, she made it known that her familial affiliations would not sway her decision. 

"One of the greatest privileges we have as Americans is a voice," she posted. "I'm proud to say I did my part, now it's your turn. ... #ImWithHer." The hashtag was what got people excited in the comments, as it was used by many associated with Clinton to show their support. 

"I wonder how the dynamics are with the in-laws... Half democrat, half republican," one Instagram user posed in the comments. "Thank you for using your brilliant mind, your voice, and your platform to spread an idea of America that is hopeful and not hateful!" wrote another. Boy, would we have wanted to be a fly on the wall when the Trumps found out.

In the moments that Karlie Kloss has shared her thoughts on politics, she hasn't held back. As described by Vogue, the supermodel is a "fervent Democrat," as is her husband, Josh Kushner. Given that her brother-in-law served as a senior presidential advisor to Donald Trump, we can imagine that their Thanksgiving is the most awkward out of anyone's. 

"It's been hard," Kloss said, noted by Vogue. "But I choose to focus on the values that I share with my husband, and those are the same liberal values that I was raised with and that have guided me throughout my life." 

When appearing on the front cover of Forbes in 2017, just months into the Trump administration's term, Kushner spoke about his political affiliations and what he hoped to see in the future. "It is no secret that liberal values have guided my life and that I have supported political leaders that share similar values," he told the magazine. "But neither political party has a monopoly on the truth or on constructive ideas for our country. It's important to be open minded and learn from differing opinions." We wonder what he thinks now.

Thanks to Instagram, we've been able to get an idea of what Karlie Kloss and Ivanka Trump's relationship is like. As noted by Hey Alma, the dynamic between the two is icy on social media. Back in the early days of her relationship with Josh Kushner, Kloss was comfortable engaging with Trump's Instagram and liked her posts fairly often. But 2015 marked a turning point, and Kloss started mostly just engaging with Trump's photos of her children. Come 2016 and Kloss didn't like a single post of Trump's. 

Fast-forward to Kloss' engagement Instagram post in July 2018, and Trump couldn't have gushed more. "So, so happy for you and Josh! I feel blessed to have you as a sister (!!!) Karlie and look forward to the decades of happy memories we will create together as a family!" she commented. Kloss didn't respond, and the comment has since been deleted. 

Trump took things far again when she posted a video on Twitter watching Kloss on Project Runway – but unsurprisingly, Kloss didn't engage (she doesn't even follow Trump on Twitter). We might be looking into things too closely, but it doesn't seem like everything is peachy between these two.

Things may have been icy between Karlie Kloss and Ivanka Trump over the years, but the two were able to put aside their political differences in 2019, when they took a trip to Rome, Italy together with their husbands. Honestly, we would travel with just about anyone if Rome was on the itinerary. As noted by Just Jared, Kloss and her husband were spotted doing some sightseeing over the weekend they were in the city. On the same day, Trump and her husband were seen on the other side of town getting some shopping in. 

Later in the day, the two couples met up for lunch (accompanied by Trump's Secret Service detail, we should add). Maybe they all needed some time to themselves during the day, but things looked cheery between the four of them. Trump clearly knew how to appeal to Kloss' fashion career because, the day before, she and her husband were seen with Kloss at the wedding of fashion designer Misha Nonoo. Despite any tension, their Rome weekend all seemed to be very civil.

Talk about an awkward moment. While serving as a host and judge on designer competition show Project Runway, Karlie Kloss was challenged by a contestant and, to make matters worse, was faced with a painfully tense question posed to her about her in-laws. Contestant Tyler Neasloney was facing Kloss when he asked her about a dress he had designed — specifically, he asked if she would wear it to an occasion. "Not even to dinner with the Kushners?" he asked, as noted by Vogue. 

The fashion magazine reported that Kloss was visibly taken aback by the question, as were the show's other competitors. Kloss' reaction and facial expression when asked the very charged question quickly made its way to social media, and although Neasonley apologized later in the show, he was quickly sent home. 

"I was honored to be one of the first memes of the decade," Kloss said about the exchange on Watch What Happens Live. "But honestly, the real tragedy of this whole thing is that nobody is talking about how terrible that dress was. That's why he went home. And no, I would not wear that dress to any dinner." Yikes.

When appearing on Watch What Happens Live with Andy Cohen, Karlie Kloss was questioned about the dynamic she has with her in-laws and her relationship with Jared Kushner and Ivanka Trump. In response to Cohen's questioning, Kloss told him to "ask [her] anything." And Cohen jumped on the opportunity because he asked her if she was "on the same page politically" with the Trumps. Kloss did not hesitate to answer succinctly, putting her feelings on the matter in simple terms. "Andy, I'm sure I'm not the only person in this country who does not necessarily agree with their family on politics," she said. 

Of course, Kloss and her husband, Josh Kushner, have been together since 2012, far before the idea of a Trump presidency with a heavy hand from Jared Kushner came to fruition. The political situation that did arise has been hard for the couple, but she said she was proud of her marriage and her husband. 

"I'm so proud that he's my partner," Kloss said. "It's not been easy, but it's worth it, and I would make that same decision a million times again."

We can imagine that things got tense after Karlie Kloss expressed her dismay about family separation at the border on social media in June 2018. The divisive Trump administration policy that took children away from immigrant parents sparked a lot of outrage, and Kloss joined in on sharing her thoughts. 

"It's not the time to say 'there are no words,' there are many. Politicizing the lives of these defenseless children and ripping them from their parents is heartless," she wrote on Instagram. "We have to be the voices for these kids, and I support anyone standing up to do right by them ... No matter what side of the aisle you are on — speak up. #KeepFamiliesTogether." 

If anyone wasn't super clear on Kloss' political affiliation and thoughts, they were brought into the know after this. From our research, it's clear that the Trumps and Jared Kushner didn't publicly speak out against Kloss and her very public rebuking of the family separation policy, but we can imagine that there were some awkward conversations about it. People in the post's comments were glad she spoke out, with one saying, "Beautiful inside and out.... Thank you Karlie."

We do not envy Karlie Kloss' unique political position — being married to someone whose name is so closely associated with President Donald Trump seems to come with a lot of consequences, and when the supermodel has shared her thoughts on social issues, she has been blasted for it. 

As noted by Vulture, Kloss took to social media in May 2020, and posted a Cleo Wade quote that said that addressing racism starts by "healing it in your own family." That was clearly not well received by some, given Kloss' in-laws, and actress Tavi Gevinson went off in the comments. 

"Karlie, give it a rest," Gevinson started. "You have a lot of nerve to make a show of championing girls' coding and your other causes while only politely disowning your family in public (lmao @ you ignoring ivanka on social media; she still went to your wedding). I can't believe you're not more embarrassed not just by them but YOUR decision to only publicly disown their politics in polite ways so you can have it both ways." We'll give you a moment to take all that in.

Well this might just be the most awkward detail about Karlie Kloss' relationship with the Trumps yet. We all know just how contentious the 2020 presidential election was (and many of us are still recovering), and Kloss made a splash when she posted a photo of herself voting on Instagram. The post was significant for a number of reasons. 

First, Kloss made a point of highlighting her vote-by-mail plan. "What's your voting plan?" she asked her followers. "This was mine — signed, sealed, (notarized), and delivered." As we know, the Trump administration circulated a lot of misinformation about voting by mail, which just made Kloss' very public voting plan that much more contentious. Secondly, Kloss included some choice hashtags that made her voting intentions very obvious, including #voteBLUE and #scienceoverfiction. To top it off, she wore a Joe Biden/Kamala Harris face mask, so we really wonder how that went down with the in-laws. 

Just a few weeks later, Kloss posted a photo of Biden and Harris hugging with the caption, "President-elect Joe Biden, and MADAM Vice President-elect Kamala Harris," with blue heart and American flag emojis included. Interesting.

The world expressed outrage over the police killings of innocent Black people in 2020, and one of the biggest cases was the killing of Breonna Taylor. Karlie Kloss, like many celebrities, took to social media to call for the arrests of the officers involved. But unlike other people in the public eye, Kloss had to deal with the fact that Donald Trump reacted the way in which he did, given that he's her sister-in-law's father. 

"It's been 160 days since Breonna Taylor was murdered in her home ... We need to stay loud, keep demanding justice for Breonna and her family, and #SAYHERNAME," Kloss posted on Instagram. The president did not share her sentiment. As noted by Politico, Trump offered his condolences to Taylor's family, but also called for support of law enforcement. "I think it's a sad thing," he said. "I also think it's so sad what is happening with everything about that case — including [to] law enforcement." 

It was later noted on Twitter that a reporter asked Trump about Taylor's murder multiple times, to which he said that he had an emergency phone call and quickly left. We'll let this one speak for itself.

Babies are wonderful, but welcoming a new bundle of joy into a family that's riddled with awkward conflict is not a situation we envy, and as noted by Yahoo! News, things could get sticky for Karlie Kloss and Josh Kushner in this stage of their lives. Karlie Kloss, who has had a stunning transformation over the years, announced via Instagram in November 2020 that she and Kushner were expecting their first child, and although the news was warmly welcomed by so many, it could have some complications. 

As Yahoo! News put it, the news could mean that Kushner will have to revisit his relationship with his family, especially his brother, now that a baby is going to be in the mix. It might be a good time for the brothers to address some comments that were made last year, too. As noted by Yahoo! News, author Vicky Ward included in her 2019 tell-all book Kushner, Inc.: Greed, Ambition, Corruption that Jared Kushner had some choice words for Kloss, including that he was "hoping [Josh will] move on," that Kloss is "not that smart," and that the family — who were very welcoming to Ivanka Trump — felt the same. Yikes.