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Can Ivanka Trump and Karlie Kloss’ friendship survive the presidency?

What does the future hold for the former best friends who now find themselves holding opposing views on the Trump presidency? Tom Leonard explores the dilemma they face

By Tom Leonard

On the court the players were slugging it out for the US Open title - but as the tournament came to a climax last September, all eyes were on the VIP box. There was Wendi Deng, Russian gallerist Dasha Zhukova, Princess Beatrice and billionaire Hollywood mogul David Geffen.

As for the two elegant blondes book-ending the celebrity front row - that was Karlie Kloss and Ivanka Trump. The pair - Ivanka in a cream jumpsuit; Karlie in a white sleeveless top and blue skirt - were photographed laughing and chatting, looking, to the casual observer, like two friends who didn't have a care in the world. 

You may remember those pictures, for the simple reason that you won't have seen anything like them since. What has intervened has been the small matter of one of the most divisive presidential elections in US history - and the fact that many of Ivanka's smart New York friends would nowadays rather be seen almost anywhere than with her.

For Karlie, detaching herself from the toxic Trump 'brand' isn't quite so easy. After all, she and Ivanka are united by more than just their shared fame and reputations as astute businesswomen. Their other halves are brothers, Jared and Joshua Kushner. The first is Ivanka's husband who, combined with Ivanka, has a reported net worth of at least £570m and is arguably the most important aide to the President. The second is a successful entrepreneur whose firm, Thrive Capital, shot to fame after it invested early in Instagram. And for the past five years Joshua, who is worth a reported £155m, has been the boyfriend of Karlie.

The brothers, scions of an incredibly close New Jersey property dynasty estimated to be worth in excess of £1.4bn, will always be bound together by blood. But what of one-time friends Karlie and Ivanka? "You won't see another photo like the one at the tennis tournament during this presidency, I guarantee," said a New York businessman who knows both couples. On paper the 24-year-old supermodel and First Daughter have much in common. Both have modelled, both have a razor-sharp eye for marketing themselves and both have launched themselves as champions of women. Ivanka - who studied at the prestigious Wharton business school in Pennsylvania - started her career in the family business, later releasing a range of jewellery, followed by clothes, shoes and accessories. Karlie, who was raised in St Louis where her father was a doctor and her mother an advertising art director, is currently the world's third highest paid model according to Forbes magazine, with a reported income of £7.8m in 2016. She has her own range of sunglasses and her own YouTube channel, Klossy, helping to push her estimated net worth to more than £12m. 

While Ivanka has advocated for state-provided parental leave and spoken of the importance of supporting female entrepreneurs, Karlie is currently studying feminism at New York University and has supported women in tech through her initiative Kode with Klossy, which offers a free programme to girls aged 13 to 18 and scholarships to attend a full coding course with Flatiron School in Manhattan.

The two women's closest mutual friends are Zhukova (who has taken Karlie to watch Chelsea matches - a team owned by her husband, Roman Abramovich) and Deng. The latter, former wife of Rupert Murdoch, reportedly reunited Ivanka and Jared after they split in 2008. Although Karlie has never revealed how she met her notoriously publicity-shy boyfriend, the impeccably connected Deng may have played a part. She and Karlie have been friends since at least 2012 when the model appeared at a charity event hosted with Zhukova.

Yet ever since Donald Trump became President, the friends' paths have gone in very different directions. While Karlie can do no wrong in the public eye, Ivanka can seemingly do no right. Such is the misogynistic reputation of her father that many women simply feel let down by her continued support of him. As protesters organised boycotts of her products, in February the department store chains Neiman Marcus and Nordstrom dropped Ivanka's fashion line, citing 'poor performance'. In April she attended a summit on women in the workplace in Germany and was booed by the audience when she praised her father's advocacy for women. 

For Karlie, the problem with being associated with Brand Trump is obvious. The New York fashion world in which she inhabits has made clear its contempt of the new administration, with designers boycotting stores that sold Trump family fashion brands or - in the case of Tom Ford, Marc Jacobs, Zac Posen and a string of other big names - refusing to dress First Lady Melania. Perhaps more importantly, the Trump administration couldn't be further from the liberal views she espouses. On election day last year, Karlie tweeted a photo of herself filling out her ballot alongside the pro-Hillary hashtag '#ImWithHer'; she followed up by sporting the blue ribbon of the American Civil Liberties Union on the hip of her white Stella McCartney dress in protest at the President's 'Muslim ban'. Such values form a crucial part of her brand: aside from Kode with Klossy, she has given her name to Karlie's Kookies, a range of biscuits sold to provide food for children through the charity FEED Projects.

But the problem cuts both ways. As that mutual friend puts it: "This is tricky for both Karlie and Ivanka... Ivanka's been stung by so many of her old friends being so anti-Trump. I'm sure she doesn't want to be seen mixing with the sort of people who are sneering at her father." Jared recently admitted he started "exfoliating", or shedding, liberal friends as they knew he wasn't going to budge in his loyalty to his father-in-law. A source close to the couple describes it as a "fortress mentality... they're pulling up the drawbridge and making it clear that anyone who attacks the White House cannot be their friend."

In stark contrast to last year, when both couples attended the 2016 White House Correspondents' Dinner, and Karlie obligingly snapped a goofy photo of Jared and Ivanka (sticking out her tongue) for the latter to post on Instagram, this year Ivanka joined her father in boycotting the event. Neither have the two women been pictured at any events together since the US Open, though Karlie is often seen out in the company of other celebrity friends, such as Taylor Swift and New York fashion writer Derek Blasberg.

Even Joshua appears eager to put a distance between himself and the First Family, despite the fact that he and his brother have long claimed to be best friends. He's publicly stated that as a life-long Democrat he couldn't vote for Trump and told Forbes in April that "liberal values have guided my life"; he also attended the anti-Trump Women's March in Washington in January. Their relationship is further complicated by the fact that Joshua's biggest venture, a £2.1bn health insurance company called Oscar, is built around President Obama's health reforms - which Donald Trump has vowed to abolish.

Both Joshua and Karlie have stopped short of directly attacking the President. Insiders say she refuses to talk about the Trumps in interviews and even pulled out of one with an Australian TV station when it appeared they might pop the question. Sources talk of as many as five PR handlers watching hawk-like over Karlie interviews. 

Will the friendship survive? Only time will tell. For now, the two women appear to face a dual dilemma. Karlie, a savvy businesswoman whose success is based heavily on her cool, 100% liberal 'brand' only need look as far as Ivanka to see what happens when you get too closely tied to the Trump presidency. And Ivanka? As shoppers boycott her clothing brand, reports circulate that she and Jared are fed up with Washington and are re-evaluating whether to return to New York. 

Karlie and Ivanka might not be photographed out and about together any more - but in some ways, their complicated relationship with a toxic presidency means they've never had as much in common.

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