The sins of the father have shadowed Kushner’s slick ascent – now claims of contact with Moscow have landed him in a spotlight he had hoped to avoid

In the middle of December last year, Jared Kushner, the smooth-skinned, impeccably tailored and inscrutable son-in-law of Donald Trump, was riding high. He was basking in the glow of having helped his father-in-law become the most powerful man on earth; was about to take up the role of senior adviser to the President of the United States, which would make him one of the most influential people in the administration; and on the home front he and his wife Ivanka Trump were sitting on a real estate pile worth up to $740m.

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If he’d just let his elegantly thin-lapelled suits and pinstriped ties do the talking, he might still be atop that wave, lauded by some as the one voice of reason and calm in a wild and unpredictable White House. But he didn’t rest there.

Instead, he allowed himself to be lured by the Russian ambassador to the US, Sergey Kislyak, to a meeting with a top Russian banker, an alumnus of the country’s top spy academy with close ties to Vladimir Putin. Details of the discussion with Sergey Gorkov remain sketchy, but according to Gorkov himself Kushner was present in his capacity as CEO of Kushner Companies, the family real estate empire from which he had yet to step aside in preparation for his move into the White House.

Gorkov’s description suggests that money matters may have been on the table between the two men. Even more incendiary was the alleged proposal that passed between the two men about setting up a back-channel between the Trump inner circle and the Kremlin, as revealed by the Washington Post.

With that one encounter, barely 30 minutes long, Kushner eviscerated his carefully cultivated image and propelled himself into the center of the inquiry into possible links between Trumpworld and the Russians. He now finds himself as a person of interest, though not a target, of the FBI investigation.

Next Thursday the conflagration will flare up again with the testimony to the US senate intelligence committee of James Comey, the FBI director sacked by Trump. Kushner can expect to be dragged into that arena too, having reportedly argued firmly in favour of Comey being dumped.

The revelation of the Gorkov meeting in December has landed Kushner in a place that he has tried hard to avoid: the public spotlight. On a more visceral level, it has threatened the mission that has driven him ever since he was plucked from obscurity to lead the family business at the age of 24 – his desire to redeem the Kushner name after the disgrace and imprisonment of his father.

'Jared was driven by a desire to vindicate his father. His pre-Trump life was focused on that single aim'

Charles Kushner served 14 months of a two-year sentence imposed in 2005 for illegal campaign donations, tax evasion and witness-tampering. In an act of retaliation against Charles’s brother-in-law, who had been cooperating with federal prosecutors, he had hired a prostitute to seduce his relative-turned-snitch, had filmed their embrace, and then posted the tape to his sister, who promptly presented it to law enforcement.

The trauma of the Kushner patriarch’s downfall, and its seismic impact on Jared, who was obliged to step up and take his father’s vacant seat, offers an essential clue to understanding how he finds himself today in such troubled waters. “It was always all about the father,” said a former top executive in one of Kushner’s holdings who worked directly with him. “Jared was driven by a desire for redemption, to vindicate his father. A great deal of his pre-Trump life was focused on that single aim.”

While the elder Kushner was behind bars in a federal penitentiary in Alabama, his son spoke with him on the phone every few days and visited the prison regularly at weekends. After he was released in 2006, Charles once again became a fixture at Kushner Companies HQ. “Daddy,” Jared would call him in front of senior executives.

Such was the jolt of Charles Kushner’s incarceration, that by the age of 26 Jared was already taking the lead on billion-dollar real-estate deals. Part of the redemption strategy that he pursued as the new head of the family was to shift the business from its New Jersey base to the more glamorous and much more high-stakes environment of Manhattan – one of the many striking parallels between Kushner and his father-in-law, who also as a young man relocated the Trump real estate operation from the outer boroughs into heart of New York City.

The new Kushner Companies home at 666 Fifth Avenue, opposite the Rockefeller Center, was the manifestation in glass and aluminium of Jared’s redemptive ambitions. It was bought in 2007 for $1.8bn, a record-breaking sum for an individual building in the US at that time. The vast expense caused jaws to drop in Manhattan real estate circles, and continues to cause the Kushner family palpitations given the vast debt burden and cost of planned redevelopment, forcing the company to go looking for loans in controversial locations.

FBI investigators delving into Kushner’s December meeting with the Russian banker Gorkov are likely to be alert to any sign that 666 Fifth Avenue came up in conversation. The Kushners have a hole of at least $250m to fill in the financing of the 41-storey tower, a particularly challenging task after negotiations with Anbang Insurance Group, a Chinese company with close ties to the Chinese government, collapsed in March.

Facebook Twitter Pinterest Jared Kushner and Ivanka Trump make their way to board Air Force One before departing from Ben Gurion airport in Tel Aviv. Photograph: Mandel Ngan/AFP/Getty Images

The Senate intelligence committee has indicated that it plans to question Kushner when he appears before members as part of the Russia investigation about whether he addressed the issue of the financing of 666 Fifth Avenue with Gorkov. The White House has insisted that the subject never came up, but in his statement Gorkov said that for his part he saw the meeting as a stop on his tour of “business circles of the US, including with the head of Kushner Companies, Jared Kushner.”

Kushner stood down as CEO of Kushner Companies shortly before taking up his new role at Trump’s side in the Oval Office. He has also gone some way to divesting assets that could cause a potential conflict of interest as he engages with federal government business.

But specialists in government ethics say that his past life as a real estate tycoon makes him vulnerable to potential conflicts of interest inside the White House. Kushner has provided the Office of Government Ethics with a 54-page filing listing his assets and stating which he has divested in a bid to avoid such conflicts, but a Washington Post analysis found that he is still hanging on to almost 90% of his holdings.

More importantly, the disclosure form reveals nothing at all about the sources of capital to which the Kushner empire is beholden for keeping its developments afloat.

Richard Painter, chief White House ethics lawyer under George W Bush, told the Guardian that Kushner’s filing fell far short of what was needed.

“In real estate it’s not what you own, it’s what you owe, and to whom. With Kushner, we just don’t know a lot of it, and that’s a serious problem. If he wants to keep his job in the White House, he ought not to remain in the real estate business which is an industry that relies on deep bank loans and debt,” Painter said.

Painter, now a law professor at the University of Minnesota, added that Charles Kushner’s disgrace could have added an extra layer of liability. “The father’s criminal record could make it difficult for Jared to get good deals from US banks, forcing him to turn to non-traditional sources of financing from shadowy foreign banks, Russian or otherwise.”

Since his new life as a public servant began on 20 January, Jared Kushner has cut an ethereal figure in the White House, his pale skin giving observers the impression that he needs to spend more time in the sun. People who have sat through meetings with him on the Middle East were surprised that he remained largely silent, and that when he did speak he tended to mumble in his trademark thin and reedy voice. Steve Bannon, Trump’s chief strategist, reportedly has a pet name for him: “the air” – in reference to the way he glides in and out of rooms like a puff of wind.

But as Bannon knows to his cost, Kushner also wields a stealthy knife. His feud with Bannon is thought to have been seminal in at least temporarily sidelining the former Breitbart chairman within the White House – although Trump’s nihilistic climate change move was signature Bannon, and demonstrated he remains a power in the land.

'In real estate it’s not what you own, it’s what you owe, and to whom'

Kushner is also known to have encouraged Trump to ditch Comey at a time when the FBI director was actively pursuing the Russia investigation. That piece of advice from a senior adviser who was supposed to offer the president cool and considered counsel now looks ill-conceived, to put it mildly.

At the centre of all this is the intriguing relationship between Kushner and Trump himself. At face value they are chalk and cheese: the younger man quiet and composed, the older man brash and impulsive.

But there are some common traits between Kushner and his father-in-law. It’s not just their similar trajectories in the real estate world. They also have a staggering level of confidence-cum-arrogance that has allowed them to take on challenges that stretch them far beyond their own experience.

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For Trump, it was the temerity of a reality TV star who thought he could be president. For Kushner, it was the chutzpah of a 36-year-old business executive without a single day spent in government who did not blink when he was given the job of bringing peace to the Middle East, dealing with Syria, ending the strife in Iraq, forging new relations with China, not to mention transforming the way that federal institutions do business. That’s his other nickname in the White House: “Secretary of everything”.

There’s one other example of Kushner’s Trump-like qualities that now seems pertinent: the boldness of a private citizen not yet in public office who allegedly discussed with a foreign banker the creation of a back-channel to the ruthless leader of a US adversary. “That makes no sense in terms of normal White House protocol and procedure,” said professor Jeffrey Berry, a political scientist at Tufts University.

At worst, Berry added, such a proposal could expose Kushner to prosecution under the Logan Act, the law that forbids anyone who is not in or authorized by government (in this case the Obama administration) from negotiating with a foreign power on behalf of the US. “There’s no reason for him to be talking to a Russian banker about US policy,” Berry said.

It all leaves Kushner so near and yet so far. He was so near to putting his father’s disgrace behind them and leading the family to a new exalted reputation. Now he has troubles of his own.