New Jersey real estate mogul Charles Kushner had a rule for his four children when they were growing up – no jeans unless they were boarding a plane. “They had to maintain a certain look at all times, as if they were living in Camelot across the Hudson,” says a childhood friend who requested anonymity.

Years later, Kushner’s children – most notably Jared, who was 24 at the time – would get their chance to dress down, boarding many flights to Montgomery, Alabama, where the Jewish billionaire/philanthropist, famed Democratic donor and child of Holocaust survivors would spend 14 months of a two-year sentence in a federal prison from May 2005 through July 2006. He had been convicted of 18 felony counts for tax fraud, witness tampering and illegal campaign donations.

The Goodfellas-style scandal splashed across the front page of The New York Times, played on nightly news like a soap opera, and rocked the Jersey Jewish community where “Charlie,” the dapper real estate developer, held sway. At the heart of the case was a Cain and Abel story between Charlie, the NYU graduate who earned his MBA from Hofstra and viewed himself as an underdog, and his older, more erudite brother Murray, the golden child who went on to earn a law degree from the Ivy League, says the family friend.

Determined to prove himself, Charlie started a real estate firm in 1985 with his father Joseph, a tough, Polish-born partisan who was known as one of the Holocaust Builders, a group of survivors who resided in northern New Jersey and became construction and real estate developers in the Garden State. When Joseph died nine months later, Charlie brought Murray into the fold, but the two soon began to clash over deals. Charlie, the scrappy risk-taker, grew resentful of his cautious brother who he claimed was hindering him.

It led to an epic family feud and a lawsuit a few months later in which Murray alleged Charlie owed him money from their partnerships. The matter was settled out of court, but was followed by a second lawsuit in 2002, in which the Kushner Companies bookkeeper questioned funds Charlie had diverted to then-New Jersey Governor Jim McGreevey with whom he tried to buy influence.

The fall from grace was epic, transforming the perennially bronzed, silver-haired Jack Kennedy type into a disgraced felon. And the one who seemed most stung, according to those who spoke with Haaretz, was Jared, who idolized his father.

The traumatic episode proved formative, molding Jared for a future he couldn’t have foreseen, say sources close with the family. Kushner was in the throes of a New York University dual Masters in Law and Business program when he was thrust into the unglamorous job of mopping up the family mess. But at the age of 24, with no real job experience, he rose to the challenge of being entrusted with the reigns of his father’s sizable real estate firm, Kushner Companies. On weekends, he’d fly down to see his dad.

Those same qualities that emerged under duress — a cool competence, grace under pressure and familial devotion — are the ones that have endeared him to his father-in-law, says a business associate, noting that Jared and Trump partnered on a joint venture two years ago in Jersey City, New Jersey, which earned him the trust of the president-elect when he needed someone to run his campaign like a chief operating officer would. Trump hit the home stretch against ever-growing odds, reportedly battling allegations of sexual assault; of swindling Americans of millions of dollars through Trump University (which he settled out of court for $25 million last week in New York); violating IRS rules when he used $25,000 from the Trump Foundation to contribute to the campaign of Florida Attorney General Pam Bondi, who had initiated a separate investigation into Trump U but dropped it after receiving the gift, prompting bribery allegations; and of bankruptcy and debts to China, Goldman Sachs and others to the tune of $650 million.

Trump’s 35-year-old son-in-law emerged as the man behind the curtain, pulling the strings and helping the wizard of id deflect blame through a carefully calibrated combination of smokescreens, mirrors, schemes and stunts. It was familiar turf.

Some of his strategies were home runs – his creation of a $90 million digital operation, in which he collected data on millions of Trump supporters, helping pave the way to victory. He also scored points with the Jewish world, arranging for Trump to meet with Israeli Prime Minister Benjamin Netanyahu, a man who decades earlier had come currying favor from his Democratic dad, a staunch Zionist and major philanthropist.

Like father, like son

Not all of Jared’s maneuvers, however, pointed to a halo over his head, but rather underscored near-Machiavellian ambition and a taste for the tawdry beneath his guileless, even pristine veneer.

In October, the Washington Post reported it was Kushner who masterminded the publicity stunt that brought Paula Jones and a cadre of other women who alleged sexual harassment by Bill Clinton to the last presidential debate, and even tried to get them seated in the family box.

It nearly got them ejected.

Donald Trump, from right, and Mike Pence, arriving with daughter Ivanka Trump and her husband Jared Kushner at the 2016 the Republican National Convention in Cleveland.Bloomberg

“Like father, like son,” says the childhood friend. “It didn’t surprise me in the least. What is shocking is that he’s on the verge of becoming the de facto president of the United States. I never would have imagined that – not in a million years.”

Indeed, as the poker-faced Kushner segues from his multimillion-dollar Park Avenue co-op to the White House, many even in his own Upper East Side bubble are wondering who he really is.

When his wife Ivanka Trump famously underwent her conversion process to Judaism, shul goers at the Kehilath Jeshurun synagogue would gawk as the leggy glamazon, a “shiksa goddess” trophy wife for the shy son of a disgraced macher, would sashay her way into services and lessons. Jared and his wife are more social with power couples and moguls outside the school – Barry Diller and Diane Von Furstenberg, Barbara Walters, Rupert Murdoch and his ex Wendi Deng, who famously reunited them after Ivanka broke off the relationship, sore that Jared didn’t stand up to his father who insisted she convert to Judaism, according to The New Yorker.

To Deng, Ivanka was the perfect match for Kushner, another child of privilege whose father made his fortune in real estate, who withstood family scandal, in her case when she was only 8 years old, went on to graduate from an Ivy League school, rising above the fray and joining the family business, ever-loyal to her father and sporting an impervious, near flawless façade, which she’s since parlayed into a fashion label, all-too-happy to market on the campaign trail. Always measured in her words like her husband, Ivanka was dubbed “the greatest enigma of 2016” in a Huffington Post profile that gave a nod to her “marketing genius,” though one can see Jared’s influence here, too. The master strategist deployed Trump’s greatest asset – his daughter – to offset his greatest handicap: women.

When you ask how Jared, a former dark horse, transformed himself into such a winning thoroughbred, there are a few stories that emerge. The first is how this unremarkable student at Frisch High School in Paramus, New Jersey, graduated from Harvard with honors – and a hefty profit. He would read “Crain’s New York Business” in the lunchroom, his former roommate Nitan Saigal told The New Yorker, and wound up buying buildings in a nearby suburb, converted them into condominiums and netted $20 million on the side.

The other is how he set his sights on Manhattan, selling his father’s mid-Atlantic holdings to AIG for $1.9 billion, at the end of the bubble, earning a profit of $1 billion, which he used to buy his first New York building, the iconic 666 Fifth Avenue in 2007 for a record price of $1.8 billion.

He also set about rehabilitating the Kushner name by trying to control the beast he blamed for tarnishing it – the press.

So in 2006, he purchased the ailing New York Observer, a cult Upper East Side newspaper that chronicled society, was known for its irreverent, insider coverage and its intellectual writers and editors. He has since dropped “New York” from the title, losing a fundamental piece of its identity, shuttered its print edition last week and is focused on driving readers to its website, which judging by its new editorial mix seems to peddle the same left-bashing, anti-Hillary and Obama conspiracy theories and Putin-elevating narratives Trump expressed during debates, press briefings and at his rallies. “Journalism is not his [Jared’s] priority, and he knew nothing about it when he bought the paper at 25,” says political writer Ross Barkan, a former Observer reporter who quit after learning that editor-in-chief Ken Kurson helped draft Trump’s AIPAC speech. Though the newspaper was supposed to remain “neutral,” it became clear that Kushner wanted to take it in a less objective direction.

By various reports, Jared burned through editors the way he burned through money in the real estate market, or the way his litigious father-in-law burned through lawyers, not quite understanding how the field works, making outrageous demands that seasoned professionals would balk at and be unable to fulfill. The New York Times reported that the Observer had approached a struggling freelance writer, who was working at the time as a manager of an ice-cream parlor in New Jersey, to write a “hit piece” on New York Attorney General Eric Schneiderman as payback for suing the president-elect over Trump University. He turned down the assignment when he surmised the paper wasn’t interested in an objective piece, he told Buzzfeed.

These and other instances pointed to a publisher who had contempt for the press and showed no interest in operating a respectable news source, but rather a tool to further his family’s profile, say insiders.

“I think he’s insecure about his intellect,” says Aaron Gell, former editor-in-chief of the Observer, who was one of those editors Kushner hired, then replaced when he installed close family friend Ken Kurson, who approached the ice-cream parlor manager and had been an advisor and speechwriter for former New York Mayor Rudy Giuliani and sat in the family box at the Republican National Convention.

“He plays things remarkably close to the vest, which seems like a good quality for a White House advisor, but it mostly seems attributable to a fear of exposing how little he knows. He’s led a very sheltered life, and he’s been trying to punch above his weight for years in the real estate and media industries. I suspect his discretion is a way of concealing his naivete.”

If Jared’s tenure at the Observer can be viewed as a crystal ball offering a glimpse into the Trump White House, it shows an administration run by ego, greed, opacity and nepotism, with no particular vision or respect for the office, or as former Observer editor Elizabeth Spiers noted on her blog: “He [Jared] didn’t particularly enjoy owning the paper – but he didn’t want anyone else to own it, either. I imagine Donald Trump is going to feel (or does feel already) the same way about the presidency.”

It also makes people wonder whether Kushner is the one secretly stoking Trump’s incendiary relationship with the press.

Peace in the Mideast

Among Trump’s more noted assertions when he met with the New York Times on Tuesday in an attempt to mend fences, was his prediction that he would bring peace to the Middle East and touted his Orthodox son-in-law as the architect of the deal, which drew skepticism from media pundits and foreign policy experts.

“Dennis Ross and [Henry] Kissinger spent lifetimes devoted to the craft of diplomacy and the region, and came up short. Jared spent less than a decade stabilizing a real estate empire. He won’t come up short enough to even be considered having come up short,” says an independent consultant on Middle East affairs who spoke to Haaretz.

“Michael Oren, the former Israeli ambassador to the United States, is an absolutely brilliant guy, but as smart as he is, he didn’t get it. I’ve worked with many Israeli ambassadors. There’s a protocol you follow and intricate details you need to know on the foreign policy front. And as far as I know, donating tens of thousands of dollars to AIPAC and going on trips to Israel, as the Kushners have, don’t make up for actual groundwork.”

But lack of experience has never deterred the 35-year-old from diving into unknown waters headfirst, even if the results aren’t always successful. Insiders say Jared, like his father-in-law, seems to play by his own rules.

“Look at the way he [Jared] changed the Observer’s format four times over the years he’s owned it, from broadsheet to tabloid, then to broadsheet again and then back to tabloid. And now he’s folded it altogether,” says Gell. “The problem is, he doesn’t have any set convictions of his own and as a result he can be easily manipulated as long as he’s allowed to feel as though he’s being decisive.”

The revenge of the Nebachs

And that’s the scary part, notes a political consultant who has been an advisor on campaigns both domestically and in Eastern Europe. For someone who’s led a privileged life, attending Harvard then running his father’s company, marrying into one of New York’s most socially prominent families, buying a newspaper to ensure membership into the elite, he seems to harbor a giant chip on his shoulder. Call it the revenge of the nebach. That bitterness, whether directed against the intelligentsia, Manhattan or the two-party political system he claims is “rigged,” that victim narrative of the poor, embattled, rich white man, is one he shares with his father-in-law and seems to pervade the fascist, populist bent of the Trump campaign, adds the political strategist.

Trump and Kushner’s us-against-them conspiracy theory speaks more of entitlement and a bridge-and-tunnel [for Trump, Queens, for Kushner, New Jersey] inferiority complex, than what most Americans who voted for Trump may feel – which is anger about employment, lack of money, health care and, of course, the “other,” that immigrant who has stolen his job. The Trump campaign’s exploitation of that anger and refusal to accept responsibility for its nefarious consequences is what the political strategist finds dangerous.

While Kushner has dismissed the implication that Trump’s chief strategist Steve Bannon, who ran Breitbart News, is responsible for mainstreaming these racist views by claiming that he, too, has aired views that aren’t necessarily his, Richard Cohen, president of SPLC says that Bannon needs to be held accountable for the alarming rise in hate crimes since Trump’s victory and must go if the president-elect intends to make good on his pledge to unite all Americans.

“Whether Trump or Stephen Bannon is anti-Semitic or not is not the issue. People who hate now have license to say whatever hatred they may have,” says Michael Berenbaum, a Holocaust scholar who has known the older Kushners through his work as deputy and project director of the U.S. Holocaust Memorial Museum. “We have an explosion of the expression of hatred and a fact-free zone. Look at all the fake news that tainted this election season. In the words of the late, great New York senator Daniel Patrick Moynihan: ‘Everyone is entitled to his own opinion, but not his own facts.’”

With swastikas and hate crimes on the rise in America, neo-Nazi gatherings like the one led by Richard Spencer of the white-supremacist National Policy Institute, proclaiming “Heil Trump” being covered on major networks, Berenbaum wonders whether Jared Kushner, however skillful, can contain the floodgates of bigotry, racism and anti-Semitism his father-in-law’s campaign has unleashed.

“Trump has shown he can manipulate anyone,” he says. “And he has. He’s also relied on Jared Kushner, who has become his grip on reality. But I fear controlling all this hate that has been unleashed may be too much for him.”

Priorities in place

Though many in the Orthodox Jewish community say they have pinned their hopes on this 35-year-old political ingénue and wunderkind, claiming that he, the grandson of partisans, a man who leads a modern Orthodox life, would never sanction intolerance, others point to his association with Bannon. “His presence at Trump Tower is reassuring,” says a New York-based lawyer who consulted briefly for the president-elect years ago and did not vote for him. “Good to Jared for getting Trump to listen to him. He doesn’t take counsel from anybody.”

While many Jews on the right see Kushner as a great Hebrew hope, many of those on the left and center view him as as the embodiment of an isolationist, shteytel mentality that sanctions intolerance as long as it isn’t directed at Jews or Israel.

“Kushner says, ‘you’re blaming me for the rise of anti-Semitism?’ But the answer is you have a responsibility,” says Lincoln Mitchell, a former Observer political reporter who quit last summer when Kushner wrote an editorial defending Trump after he tweeted an image of Hillary Clinton with a Jewish star and piles of money that was condemned as anti-Semitic. “I care about his access. If he had stood up right then and there when that Tweet with Hillary’s face and the Jewish star first appeared and said, ‘I love my father-in-law, but … ,’ if he would have said, ‘I want to make this clear publicly. Donald Trump owes us an apology,’ but he didn’t. If he had done that, or said now: ‘I may not like what Stephen Bannon has said or promoted, but I don’t think he’ll round up Jews.’ But his silence is very hurtful to millions of patriotic Jews who have served in the military, paid taxes and helped build this country. He keeps getting a chance, and he’s not doing anything. This is the most anti-Semitic administration we’ve ever seen, and Jared is not standing up for American Jewry, and there’s no getting around that.”

When asked about the campaign’s silence over their many white supremacist fans, Kushner told Forbes: “Trump has disavowed their support 25 times … I don’t know if he could ever denounce them enough for some people.” But as Richard Spencer’s minions raised their hands in the Nazi salute in Washington, D.C. and yelled “Heil Trump!” last weekend, the only things that prompted angry tweets from the present-elect were “Hamilton” and “Saturday Night Live.” He has not repudiated racist nationalism 25 times or even once in a Tweet, but has retweeted from white supremacists 75 times, Fortune reported last July.

The Holocaust was woven into each Kushner simcha, reports the childhood friend who recalls how Rae and Joseph Kushner’s triumph over the Nazis as partisans was the thread that bound the generations. Jared and his siblings would recite poems about their grandparents at their own Bar and Bat Mitzvahs.

“‘The Holocaust was very bad, and we’re not happy, we’re sad,’ is how one of the lines might go,” says the friend. “I think Joseph, who was part of a group of survivors known as the Builders and who literally built the house where Jared grew up, would be very upset if he were alive today, to see his grandson enabling the hate now … I’m speechless.”