Donald Trump’s inauguration as President of the United States was a divisive day around the world, but for Joshua Kushner it was particularly confusing. His brother Jared is a senior Trump advisor and his sister-in-law is the new president’s daughter.
Depsite the family connection to the Oval Office, the 31-year-old venture capitalist spent his Saturday scoping out the women’s march on Washington, DC, where chants like “Hey, hey, ho, ho, Donald Trump has got to go” filled the air.
Mr Kushner told fellow protesters he was there “observing”, according to Washingtonian.
— Benjamin Freed (@brfreed) January 21, 2017
A day later, he was in the White House, posing for photos with his elder brother Jared.
Last week, the US Department of Justice ruled Jared’s appointment did not violate anti-nepotism laws despite concerns to the contrary.
To avoid any conflicts of interest, the 35-year-old said he would not accept a salary and vowed to “divest himself of substantial assets” including his ownership of the New York Observer paper, which he has owned since 2006.
His lawyer told The New York Times this divestment would in part involve transferring his ownership in some assets to his brother.
Indeed, Joshua – who has previously described Jared as his best friend – is perhaps one of the few people who can relate to his brother’s struggle to reconcile personal interests with familial obligations.
In August 2016, Joshua made headlines when his spokesperson told Esquire magazine that Josh was “a lifelong Democrat” who “will not be voting for Donald Trump in November”.
A “friend of the Kushner family”, however, told the magazine: “He may not vote for Donald Trump … But will he be objecting to a pardon for his father, which is surely what will happen if Trump gets elected? I think not.”
Joshua and Jared’s father, real estate developer Charles Kushner, was in 2005 convicted of tax evasion, witness tampering and illegal campaign donations.
Some have speculated that Jared’s involvement in his father-in-law’s campaign was an elaborate attempt to redeem his family’s name.
Joshua’s apparent deviation from his brother’s steadfast campaigning for Mr Trump set tongues wagging, but was unsurprising given his personal life.
The Harvard-educated Joshua has dated supermodel Karlie Kloss for four years. Ms Kloss, 24, is well-known for her work in encouraging women to become involved in the tech industry.
In April 2016, then-president Barack Obama name-checked her in a speech at the White House Tech Fair, calling her a “supermodel and super-coder”.
S U R R E A L does not even begin to define the day. I never dreamed I would be invited to The @WhiteHouse, let alone hear the president say my name. 🙊 Such a cool moment, but not as cool as meeting the brilliant student scientists, inventors, and tinkerers standing behind POTUS. #WHScienceFair
A video posted by Karlie Kloss (@karliekloss) on
Ms Kloss is a member of outspoken feminist Taylor Swift’s “girl squad” and counts staunch Hillary Clinton supporters like Christy Turlington and Lady Gaga as her friends.
Ms Swift herself was recently slammed on social media for failing to appear at the women’s march and criticised for not expressing a clear political opinion in favour of Mrs Clinton by her majority female fans.
While Ms Kloss has never explicitly revealed her political opinions, she’s party of an industry – the fashion world, to be specific – that’s overwhelmingly anti-Trump.
The same designers who have championed Ms Kloss – Marc Jacobs, Tom Ford, Phillip Lim – refuse to dress Melania Trump.
And his girlfriend isn’t the only thing testing Joshua’s loyalty to his family’s cause.
Joshua founded the health insurance startup Oscar Health in 2012, aiming to simplify health insurance and take advantage of the independent insurance market created by the Affordable Care Act (also known as Obamacare) Barack Obama implemented in 2010.
Recently valued at over $US2 billion, Oscar could face financial or at least structural challenges if Mr Trump fulfils one of his key campaign promises: to repeal Obamacare.
Last week, Mr Trump signed an executive order to “minimise the unwarranted economic and regulatory burdens of the Act”.
Joshua and his business parter Mario Schlosser were forced to issue a statement on Oscar’s website following Mr Trump’s election regarding the future of the company.
“In light of the recent election and the changes the new Congress and Administration may bring to American healthcare policy, we would like to share a few thoughts about Oscar’s position in the context of these developments,” the statement read.
“What will never change is this: Oscar believes that all Americans deserve healthcare coverage that is high-quality and affordable for everyone. This is both ethically right and economically prudent.”
The statement ended by concluding Oscar Health was “in this for the long haul”.
Watch Joshua Kushner talk about Oscar Health
It’s clear Joshua has always happily marched to the beat of his own drum.
While Jared took over his father’s real estate empire, Joshua – whose net worth was last estimated at $US200 million – forged his own path in business.
In 2009 he founded Thrive Capital and began investing in savvy startups like Kickstarter. Thrive was one of the earliest investors in Instagram, recently bought by Facebook for $US1 billion.
So perhaps his divergence is to be expected and, ultimately, accepted. Otherwise it will make for some very awkward Christmas family lunches.