Jared Kushner had a meeting scheduled with a New York City councilman from Brooklyn. He just didn’t seem to know exactly why.

It was October 2013 and Kushner and a group of investors had just purchased five Brooklyn warehouse properties for $375 million — an eye-popping $50 million more than the seller expected to get. His idea was to replace the buildings with gleaming, high-end residential towers. The hitch: The plan required an onerous rezoning process and multiple layers of city approval, including a green light from local councilman Steve Levin.


The two shot the breeze in Kushner’s Fifth Avenue office — they talked about New Jersey, where they both grew up, and Brooklyn, where they both wanted to burnish their names. Kushner recommended an eatery in Williamsburg. Levin told him about Glasserie, an airy cocktail lounge in Greenpoint.

But Levin then grew puzzled about whether Kushner — the scion of a New Jersey real estate empire who has emerged as an improbable power broker inside his father-in-law Donald Trump’s transition team — understood the political levers that needed to be pulled.

“It was a weird meeting because it seemed like he didn’t understand why he was meeting Steve and what the significance was,” recalled one person familiar with the meeting. “Steve had to explain to him, ‘If you’re going for a residential rezoning, I have to approve it.’ The reaction was, ‘Oh, interesting.’”

“A head-scratching experience,” was how the person described the meeting, which left many in the industry gossiping about how Kushner had plunked down so much money without fully understanding the giant hurdles ahead.

Kushner, apparently, saw the meeting simply as a courtesy, as he talked with other city officials who he thought carried more weight. But the outcome was clear — after the luxury condo towers proved too difficult to push through, Kushner scrapped the plan and instead focused on signing commercial tenants. The buildings are now part of an up-and-coming tech nucleus. But big chunks of the property remain vacant.

To people in the real estate community who have done business with Kushner — who presides over his father’s business empire and owns The New York Observer, a small Manhattan newspaper — the deal represented a snapshot of how he operates: as a political and policy novice who trusts his own judgment and vision and isn’t scared to plow ahead even when he knows little — much like his father-in-law, Donald Trump. Kushner is soft-spoken, mild-mannered, even a bit shy. But in New York City real estate and media circles, former colleagues and business associates paint a picture of a son-in-law who has much in common, under the surface, with the brash and braggadocious president-elect.

People who know Kushner say that like Trump, he sees himself as an outsider who, despite his Ivy League pedigree, scoffs at intellectual and cultural elites, and believes that, despite a mixed business track record, he possesses a “golden touch.”

Kushner — who married Ivanka Trump in 2009 at the Trump National Golf Club in New Jersey, with the bride wearing an Ivanka Trump Collection six-carat cushion cut ring on her finger — is now poised to play a powerful role in his father-in-law’s White House. Whether he decides to take a job inside the administration or not, he will be one of a small circle of people who have the president’s full trust and his ear.

One Trump insider described Kushner as “the most powerful person after Donald himself” on the campaign and now in the transition team, because “nobody wants to cross the family.”

Kushner has recently lost a noticeable amount of weight, as he has become consumed in the frantic day-to-day of the transition. But he appears to be along for the ride.

“He drank the Kool-Aid,” shrugged one friend who supported Hillary Clinton’s campaign, but remains complimentary of Kushner. “He thought Donald had a shot at being president, and that he had a shot at helping him.” Kushner is loyal to his family, and his view on Trump’s more extreme comments, like a Muslim ban, the friend said, is: “That’s not him. Relax, he’s just saying these things to get elected.”

During the campaign, Kushner rose quietly and quickly as a power center. He started out simply helping with the campaign’s social media and digital sides. But his portfolio quickly grew. He took over management of the online store. He hired policy adviser Stephen Miller to travel with Trump and write speeches. He spent five months orchestrating Trump’s campaign visit to Mexico.

He was also in favor of bringing on the power structure that ultimately won Trump the election: the trifecta of Kellyanne Conway, Steve Bannon and David Bossie. And he has helped to sideline New Jersey Gov. Chris Christie, who he felt bungled some aspects of the transition and failed to stand up for his father-in-law when the damaging "Access Hollywood" tape emerged. It was no great loss to the Kushners, who have long resented Christie for prosecuting their patriarch, Charlie Kushner, for tax evasion, witness-tampering and making illegal campaign contributions in 2005.

Over the past year, Kushner took on some of the most sensitive and high-stakes campaign tasks. He became Trump’s designated go-between for billionaire casino mogul Sheldon Adelson, who now sits on the president-elect’s inauguration team. He protected people on the campaign who were seen as “Jared’s guys,” like digital director Brad Pascale, whose firm was paid $90 million by the campaign — nearly 40 percent of its overall spending through Oct. 19 — and whose only prior relevant experience was building websites for Trump’s real estate ventures and Ivanka Trump’s fashion line.

Since Trump’s surprise victory on Election Day, Kushner has maintained his ever-present but publicly silent role. Kushner was there, in the background, snapping iPhone pictures in the Oval Office when Trump sat down for his first meeting with President Barack Obama, and touring the Rose Garden with chief of staff Denis McDonough. And he is there, in the foreground, in Trump Tower, exerting his growing influence on a chaotic transition process.

Kushner, the grandson of Holocaust survivors and a supporter of gay rights, has emerged as a moderate voice in Trump’s circle. Insiders said he thought the “cleanest structure” was to appoint Republican National Committee chairman Reince Priebus as chief of staff, and have Bannon, a highly controversial figure for his stewardship of Breitbart News, in the potentially less prominent role of senior adviser.

But Kushner is all in with his father-in-law, and so is his Orthodox Jewish immediate family, whom insiders describe as “big believers in Donald.”

In general, Kushner also serves as a secure line for people who want to get in touch with Trump, including people who wanted to support the campaign but were fearful of going public with it.

A Trump spokeswoman did not respond to a request for comment, and a Kushner spokeswoman declined to comment about his role in the campaign or transition team.

Despite a rich kid’s upbringing across the Hudson River in New Jersey, and degrees from Harvard University and New York University law school, Kushner sees himself as standing apart from the institutional elite and eager to prove himself on his own terms. “I grew up, a kid in New Jersey,” Kushner told the New York Times in a 2011 profile. “And I’m here with these people who are very interesting people. And I’ve been able to develop a lot of very interesting relationships.”

He stands apart, in large measure, because of his family’s history: Kushner was forced to take over his father’s company when most of his peers were still trying to score internships, after Charlie Kushner was sentenced to federal prison for two years starting in 2005.

That experience taught him that things one takes for granted could be taken away and that life can change in an instant.

Some of that has happened, again, over the past year, as his position in Manhattan society has changed. Some liberal friends stopped speaking to Kushner as Trump’s political fortunes rose.

One prominent New York political figure interviewed for this story spoke positively of Kushner’s business acumen. But the person later reached out, expressing some concerns about blowback for compliments that might be construed as support for Trump.

Today, Kushner reacts to people in Manhattan who no longer speak to him because of his role in Trump's political operation with a shrug. A source close to Kushner said he is not bothered by any of the social friction, and keeps to a very small circle that includes mostly members of the Kushner and Trump families.

Father and son were already close, but the traumatic experience of Charlie Kushner’s prison sentence appears to have forged a complicated bond. His parents, former associates said, are involved in every aspect of his life — down to overseeing the redesign of the offices of The New York Observer, which Kushner purchased in 2006. These days, Jared and Charlie often walk to work together.

Jared Kushner can be “aggressively self-deprecating,” as one former colleague put it, sometimes forcefully acknowledging that he might not be the smartest person in the room, but that he has the best natural instincts. He brags that he knows exactly who he is.

He has enough self-awareness, people who have worked with him said, to acknowledge how people see him: He jokes about the fact that people think his father bought his admission to Harvard with a $2.5 million pledge.

But some of his trusted instincts, or at least interests, seem to mirror those of Trump.

In 2007, Kushner made his first big splash on the Manhattan real estate scene by purchasing 666 Fifth Avenue for $1.8 billion — a record price for an office tower, and a deal that quickly ran into trouble, but only in part because of the recession.

At The New York Observer, which he bought when he was 25, Kushner pushed for the newspaper to launch a standalone website called “Socialite Slapdown.” It was fully his idea: to rate Manhattan’s 64 reigning socialites by “birth, brains, beauty and brio” to see “who comes out on top.”

The concept wasn’t unlike his future father-in-law’s interest in the rating and competition involved in his famed beauty pageants. Kushner insisted on launching the site against the advice of practically every editorial voice at the newspaper, many of whom cringed at what they saw as their young owner’s attempt to be an arbiter of high society with a certain degree of plausible deniability. Others saw it as a Jersey boy’s attempt to play in Ivanka Trump’s pen (the couple were on a brief break when he launched the short-lived site).

Because Kushner burst onto the Manhattan scene as a budding media and real estate mogul when he was a millennial, that also put him in social circles with older friends.

He has developed close relationships with businessmen Michael Ovitz and Rupert Murdoch, whom he considers his mentors. Sources who have spent time around Kushner said he often downplayed the yacht vacations but recounted conversations he had on “boat trips with Rupert.”

But mostly, Kushner trusts himself — and he usually has a firm idea of what he wants, even when he dips into territory that isn't his own.

At the Observer, for instance, he was distressed by a cover story about the British novelist Martin Amis moving to Brooklyn. “Nobody knows who that writer is,” he complained. He objected to the paper’s books coverage in general, arguing “I don’t have time to read novels, and neither does anybody else.” Kushner believed that Amazon was the only place where book reviews matter, that readers simply weren’t opening the Observer to read about books.

Jared is loyal to his father, whom he visited every Sunday while he served time in Alabama. But in Trump, he sees the opportunity of a lifetime to do something apart from the family business.

Some New York City business associates said it gives them hope that Kushner has influence in Trump’s small circle. Kushner has contributed more than $100,000 to Democrats over the years, including lawmakers who supported Obama’s decision to grant legal status to millions of undocumented immigrants Trump says he wants removed from the country.

“Jared is a bridge-builder,” said Douglas Harmon, a real estate broker who works with Kushner. “He would manage upward and downward with ease, grace and maturity beyond his years. I would feel comfortable with Jared in an important role in this administration more so than anybody else who is currently in the public mix for positions of influence.”