Jared Kushner’s Second Act




In the spring of 2011, right around the time Donald Trump was humiliated by Barack Obama during the president’s speech at the annual White House Correspondents’ Dinner, Jared Kushner, Trump’s son-in-law, placed a call to Richard Mack. Kushner was thirty years old, a decade and a half younger than Mack, but in many respects the men were peers. They were both scions of prominent real estate families, and in 2009 Mack and his wife had attended Kushner’s wedding, to Ivanka Trump. The two men were also business associates: Mack held some of the debt on 666 Fifth Avenue, a gleaming thirty-nine-story office building in midtown Manhattan for which Kushner had paid a record $1.8 billion in 2007.

Now, four years later, Kushner was calling about the tower, a symbol of immense importance for him and his family. Under the leadership of Jared’s father, Charles, the Kushner Companies had made hundreds of millions of dollars building and buying properties in New Jersey. But in 2004, future Trump surrogate Chris Christie, who was at the time the U. S. Attorney for New Jersey, indicted Charles in federal court on charges that included tax evasion, making false statements about campaign contributions, and hiring a prostitute to retaliate against his brother-in-law. After Charles pleaded guilty and was sentenced to two years in prison, Jared, who was just twenty-four, took over the family business. He sold the Kushner holdings in New Jersey and bought 666 Fifth Avenue. The significance of the deal lay not only in its size but in its location. Much as Trump’s renovation of the Grand Hyatt hotel three decades earlier had carried his family’s real estate empire across the East River from Queens, Jared’s purchase of 666 Fifth Avenue, just three blocks from Trump’s own trophy skyscraper, was an unmissable sign of the Kushners’ arrival in Manhattan.

By the time he spoke to Mack in 2011, Jared and his younger brother, Josh, had established a social and business beachhead in New York. Besides running the Kushner Companies, Jared was also the owner of the New York Observer, a once venerable newspaper. Josh had already started Vostu, a profitable social-game developer, and a venture firm called Thrive Capital.

Despite his evident success, however, Jared was in trouble: After the financial crisis led to a downturn in the rental market, the Kushner Companies risked an imminent default on the loans that had financed the firm’s purchase of 666 Fifth Avenue. Jared’s lenders were at his throat, and he stood to lose hundreds of millions of dollars, if not the entire building.

According to a source familiar with the call, Jared appealed to his friendship with Mack—”I am a really good person,” he insisted—and asked him to accept a substantial write-down of the loan.

Mack held firm. He had been unhappy with some aspects of how the Kushners managed the building, and, as he reminded Jared, he had a fiduciary responsibility to his investors.

Jared did not take the news well. According to the source, he began shouting into the phone, “I’ve been working my ass off!”

Mack was unimpressed. “I don’t know who the hell you think you’re talking to,” he said, and hung up the phone.

Jared was just twenty-six when he bought the thirty-nine-story tower at 666 Fifth Avenue for a record $1.8 billion. A subsequent downturn in the market caused him to scramble to preserve control of the building.

Jared was eventually able to preserve his control of the tower by ceding 49.5 percent of the building’s equity to Vornado, a publicly traded real estate investment trust. Mack, who is forty-nine, remained dimly aware that Jared had not forgotten their disagreement, but it was not until this past summer, when Elizabeth Spiers, a former editor of the Observer, wrote on her website about what she called “the Big Dick Mack Story,” that he realized the extent of Jared’s lingering animosity.

Spiers wrote that during her tenure as editor, in 2011 and 2012, Kushner had pushed for a hit piece on Mack. “If the tip he’d given me had checked out, it would have been a good story,” she wrote. “So I agreed to put a reporter on the story.” She gave the assignment to Dan Geiger, the Observer’s real estate beat reporter. Kushner called Geiger and furiously complained that Mack was a “bad fiduciary” who’d moved money around to enrich himself at the expense of his investors. (Kushner declined to comment on the record for this article, but through his publicist he denied that his pursuit of the Mack story was related to the loan on 666 Fifth Avenue.)

Geiger phoned his contacts—as Spiers wrote, he “called everyone within a hundred-mile radius”—and found nothing. He sent Kushner a detailed email outlining what his sources had said.

For a week, Geiger heard nothing. Then Kushner called him and said, as if they had not already spoken, “There’s a guy named Richard Mack, and we’ve got to get this guy.”

Geiger was bewildered. He went to Spiers, who, he says, recognized Kushner’s obsession as the “illicit powder keg” it was. “Jared insisted that it was a reporting problem,” she wrote in the blog post. To humor her boss, Spiers assigned a second reporter to the story. He, too, got nowhere; once again, nothing in the story checked out. But even this was not the end of it. Jared told Spiers to ask one more reporter, who did not work for the Observer, to look into Mack. That reporter was me.

I turned down the assignment, even though I had been friendly with Jared for many years. At the time, I knew him to be bright, charming, and polished, a pious son of a devout Orthodox Jewish family. I had never been exposed to this side of him. As it turns out, however, this side of him exists. Geiger, who now works for Crain’s, has told people that the first thing that came to mind when he found himself embroiled in the vendetta was “This guy is like his dad.”

Over the past year, Jared Kushner’s profile has risen alongside the mind-bending trajectory of his father-in-law’s presidential bid. Though Jared has no previous experience in electoral politics, he has become one of Donald Trump’s chief advisors, and much of the attention he’s received has focused on the many ways in which he’s been useful to the campaign. It was Jared who helped prepare Trump for an appearance before the American Israel Public Affairs Committee (AIPAC) in March, and Jared who helped broker a truce with Fox News when Trump fought with Megyn Kelly, the network’s star anchor. After Trump fired Corey Lewandowski, his campaign manager, in June, it was reported that Ivanka had demanded Lewandowski’s dismissal for trying to marginalize Jared’s influence. A month later, after Trump tweeted an image of Hillary Clinton and a Star of David set against a backdrop of dollar bills, Jared took to the Observer to defend his father-in-law against charges of anti-Semitism. Most recently, Jared was on hand to help Trump choose Indiana governor Mike Pence as his running mate—over and above, it did not go unnoticed, the great nemesis of the Kushner family, Chris Christie.

There is a sense among Jared’s friends and business associates that he sees the gold-plated vision of a Trump White House as the ultimate step in a carefully plotted ascent to redemption.

And yet for all that Jared has helped Trump, there is a sense among Jared’s friends and business associates that he sees the gold-plated vision of a Trump White House as the ultimate step in a carefully plotted ascent to redemption, one that began when his father’s scandal tarnished the family name. In this respect, it seems more than usually significant that both Kushner brothers have photographs of John F. Kennedy prominently displayed in their offices. Just as Kennedy’s father was forced to yield his ambitions to his sons’ generation after uttering controversial remarks during World War II, so too did the scandal that sent Charles Kushner to prison open the door for his sons—and especially for Jared—to launch their charm offensive on society at a very early age.

Jared, who is thirty-five, and Josh, thirty-one, along with their sisters, Dara, thirty-seven, and Nicole, thirty-three, grew up privileged and sheltered in Livingston, New Jersey. Their paternal grandparents, Joseph and Rae, escaped Poland during the Holocaust and immigrated to the United States in 1949. They moved to the suburbs around Newark, where they helped create a tight-knit community of Holocaust survivors known as the Builders. (“My grandfather was a carpenter,” Josh likes to tell people.) The elder Kushners belonged to the Jewish Federation of Greater MetroWest NJ, which supported Jewish charities and schools. “That generation were cohorts,” says Andrew Silow-Carroll, the editor in chief of the Jewish Telegraphic Agency, the New York–based news service. “They were very collegial.”

Joseph and Rae had four children, two boys and two girls. Charles, who earned a bachelor’s degree and an MBA from NYU and a law degree from Hofstra, was less academically gifted than his older brother, Murray, who graduated summa cum laude and has a law degree from Penn. But Charles’s drive was remarkable. He took to heart the mantra passed down from one Kushner generation to the next—”Think like an immigrant, act like an immigrant”—which was at once an exhortation to work hard and a warning not to take anything for granted.

When Charles started his own real estate company, he chose his father, not Murray, as his partner. On the rare occasions that Josh and Jared have spoken about the subject in public, they have intimated that this decision exacerbated the tension between Charles and his siblings. In an interview with New York in 2009, Jared suggested that his uncle and aunts owed their good fortune all but entirely to his father, by whom they had been “literally made wealthy for doing nothing.”

Before the scandal, Charles and his pretty dark-haired wife, Seryl, were seen as the standout ambassadors of their Orthodox community. Charles became known as the Dapper Don thanks to the natty tailoring he preferred and to his growing reputation as a New Jersey power broker. As he built his real estate company into an empire worth a reported $2 billion, he contributed significantly to Jewish charitable causes as well as to political campaigns. He supported New York mayor Rudolph Giuliani but tended to favor Democrats, including senators Hillary Rodham Clinton, Charles Schumer, and Jon Corzine. In 2001, he was the largest donor to the successful gubernatorial campaign of Jim McGreevey, a New Jersey Democrat who later appointed him to the board of the influential Port Authority.

Jared attended the Orthodox Frisch School, in Paramus, New Jersey. By some accounts, he worked hard in school, but he was not especially academic. In The Price of Admission, Daniel Golden notes that officials at Frisch were “dismayed” when Jared was accepted to Harvard, since, as one former school official put it, “his GPA did not warrant it, his SAT scores did not warrant it.” Other students in Jared’s class, the official said, were far more deserving. But Jared had a weapon that his classmates did not: his father. According to Golden, Charles donated $2.5 million to Harvard the year his son applied. Just to be safe, he also donated to Cornell and Princeton.

The disgrace that followed, for Charles and for his family, was profound.

All this lobbying to establish his family in the upper echelons of power was expensive. The scandal that eventually sent Charles to prison began in 2001, when Murray discovered that his brother had used several of the family partnerships to make political contributions without informing his relatives. Murray sued Charles in court, and not long after Chris Christie became the U. S. Attorney for New Jersey, in 2002, he launched a criminal investigation.

As Christie’s case gained traction, Charles attempted to blackmail one of his sisters and her husband to keep them from cooperating as government witnesses. He paid a prostitute $10,000 to have sex with his brother-in-law, and then sent a videotape of the encounter to his sister. The vindictive effort was for naught: In August 2004, in the face of overwhelming evidence that he had evaded taxes, made illegal campaign contributions, and retaliated against a federal witness, Charles pleaded guilty to eighteen felony counts.

The scandal made for a chilling affair, one that was severely at odds with the gracious public-service-oriented persona Charles had cultivated for public view. The disgrace that followed, for Charles and for his family, was profound. “It was very embarrassing,” says Silow-Carroll. The community, he notes, has “a self-image, largely deserved, as philanthropists and Jewish communal lions. They felt that all this nasty stuff sullied that.”

As Charles headed off to Prison in Alabama in 2005, Jared was still working on a joint business and law degree at NYU. Since a convicted felon cannot sign a contract as a fiduciary, he felt that he had no choice other than to take over the family business. In his interview with New York, he acknowledged that his father had made a mistake while at the same time insisting that Charles had been unfairly punished for his crimes. He’s made no secret of the fact that he sees his father, still, as an extraordinary man, and that he believes it his filial duty to put the Kushner name back on top.

In the wake of the scandal, Jared increasingly depended on an expanding network of older male advisors. The demographics of the group—which today includes Rupert Murdoch; Michael Ovitz, the legendary former Hollywood executive; Martin Sorrell, the head of WPP; Marc Holliday, the CEO of SL Green; Joel Cutler, a venture capitalist; Kevin Ryan, an Internet entrepreneur; and Joel Klein, the former New York City schools chancellor—were reflected at Jared’s thirty-fifth birthday party earlier this year. As one guest observed, the median age of the guests at the party, which was held at the top of the Gramercy Park hotel in Manhattan, seemed to be somewhere near seventy.

“None of it’s been him. It’s been his dad.”

The financier Ronald Perelman, who met Jared at a Lubavitch Shabbat service in East Hampton not long after Charles went to prison, recalled recently that the younger Kushner “clearly needed some comforting” after the scandal broke. Perelman invited Jared to pray with him at the synagogue in his home office in New York.

Jared openly blamed the media for his family’s troubles, particularly the Newark Star-Ledger. In 2006, in a somewhat transparent attempt to control the hand that had bitten his father, Jared bought the New York Observer for $10 million. The purchase was strategically intelligent: As a newly minted media mogul, Jared was sought out by New York’s cultural elite, and the Kushner name acquired intellectual clout for the first time.

A year later, Jared sold all of the Kushner properties—mostly residential homes—in New Jersey. He purchased 666 Fifth Avenue in Manhattan for $1.8 billion, at the time a record sum for a building in New York. His father was released from prison in time to stand by Jared’s side for the closing.

Though Charles is no longer the face of the Kushner Companies, he remains omnipresent in the hallways of the firm. Each Tuesday at 8:00 a.m., everyone at the company who is not a secretary gathers in a conference room on the fifteenth floor to discuss acquisitions, financing, and construction. Charles and Jared sit next to each other at the center of a long table, and other family members fan out from there. Josh has not attended the meetings regularly for years, but Seryl often attends, as does Nicole, who recently decided to join the business. (Her husband, Joseph Meyer, is the chief executive of Observer Media.) Under Jared’s leadership, the Kushner Companies has embarked on an impressive streak of acquisitions in New York, New Jersey, and Philadelphia. This summer the firm participated in a $340 million deal for the former headquarters of the Jehovah’s Witnesses, one of the most coveted parcels of waterfront real estate in Brooklyn. But no one at the Tuesday meeting, and no one who deals with the company from the outside, is allowed to forget who built the firm. When I called one of the Kushners’ underwriters to ask about Jared’s business prowess, he seemed startled. “None of it’s been him,” he said. “It’s been his dad.”

Compared with Charles, whose temper is legendary, Jared has a notably calm demeanor. “He’s calm, he’s smooth and sharp, and he knows how to court people,” says Doug Harmon, a veteran New York broker. Yet there is also an undercurrent of hostility that belies his polite veneer. Jared was described to me as “a little bit bullheaded” and “a little bit of a bully” by one person; another said that when he gets mad, “the loss of composure is the shock because he’s always so completely controlled.”

Five buildings owned by the Jehovah’s Witnesses will become part of the larger Brooklyn Tech Triangle. They were sold to Jared Kushner, the Kushner Cos. CEO, and RFR.

Several sources told me that in 2015, Jared tried to thwart a real estate negotiation that involved J. Walter Thompson, a subsidiary of WPP, the advertising conglomerate led by his friend Martin Sorrell. Jared had no financial stake in the matter, but he insisted, following many hours of due diligence, that WPP was headed down the wrong path. After WPP’s board ignored his advice and approved the deal, Jared attended a meeting at the company and told a senior executive at WPP, “You’re the stupidest person I’ve ever met in this business.” (A spokesman for WPP would neither confirm nor deny the incident.)

Then there is Jared’s standoff with Steve Roth, the CEO of Vornado, the $20 billion real estate investment trust that acquired 49.5 percent of 666 Fifth Avenue in 2011. The deal allowed Jared to keep control of the building but valued it at a mere $820 million, a steep decline from its $1.8 billion purchase price. According to the New York Post, Jared believes that the tower should be converted to a retail mall beneath luxury condos, and he is committed to a proposal from the firm of the late Zaha Hadid. Other sources, however, say that Roth believes the building is worth more as office space. Roth, who is seventy-four, and who recently joined Donald Trump’s economic advisory team, did not respond to a request for comment, but he has told people in private that he despises what he sees as Jared’s arrogance. According to several sources, meetings between Vornado and the Kushner Companies regularly become shouting fests, though one source says that most of the screaming is done by Charles Kushner. Meanwhile, the building is stagnating, and its fate is unlikely to be settled until one party buys out the other.

For those involved in the ruthless world of New York real estate, none of this unpleasantness is surprising. But overt aggression has not gone over well in the more sensitive environs of the New York Observer. A source close to Jared says that he did not understand, when he bought the company, how much resistance he would face from the journalists who worked there. In 2007, he appointed Bob Sommer, the Kushner Companies’ publicist, as the newspaper’s president. Sommer was given instructions to “rein in” the paper’s much-revered editor, Peter Kaplan. (Kaplan and Sommer both resigned in 2009; Kaplan died four years later.) At a holiday party for the Observer a few years after he bought the newspaper, Jared implored the staff to redouble its efforts, adding that worse economic times were to come. When Aaron Gell, the editor at the time, took the microphone and thanked everyone for their hard work, the gesture seemed to irritate Jared. (Jared’s publicist says that he liked Gell and cannot recall Gell’s speech or his own.) Ken Kurson, a Kushner family friend—and longtime business columnist for Esquire—is the current editor of the Observer, its fifth in seven years.
It is widely believed that the quality of the journalism in the Observer has declined under Jared’s ownership, but he has had much more success with the Commercial Observer, a real estate spin-off. According to Bill Rudin, a developer, the Commercial Observer has become a “must-read” for developers and brokers, thanks in large part to the paper’s Power 100 list. The list is celebrated at an annual event, complete with trophies, that has been attended by Michael Bloomberg and, of course, Donald Trump. “It’s the closest the industry gets to an elegant Oscars evening,” says Doug Harmon, who shared the 2016 Deal of the Year award. “I bet most look at the list and can’t figure out why they aren’t featured more prominently.” (If so, Richard Mack is not one of them: Though his firm was once number forty-one on the list, it was dropped after his phone call with Jared. Mack knew exactly why. He told the odd employee who fretted about the company’s absence, “We are never going to get on that list—and don’t worry about it.”)

In 2007, Jared started dating Ivanka Trump. The pair became a boldfaced item—their vacations were photographed by paparazzi—and in many ways the relationship seemed perfect. Jared and Ivanka, whom he calls Iva, shared a deep knowledge of real estate, and they were both the children of controversial fathers to whom they were unwaveringly, sometimes blindly, loyal. As Kenneth Pasternak, a friend and business partner of the Kushners’, put it, “You send your kid to Harvard, you network him, and he marries Ivanka Trump. I mean, you couldn’t write that script, right?”

As it happens, however, Jared’s marriage to Ivanka was not a foregone conclusion. The couple have been married for seven years and have three children together, but during the early days of their relationship Seryl Kushner had expressed concern that Ivanka wasn’t Jewish. The couple broke up, and they reunited only after Ivanka agreed to convert to Judaism. Even then, according to Bob Sommer, Charles Kushner remained skeptical. He made Ivanka’s conversion as testing as it could be. “This wasn’t like, ‘Talk to a rabbi, read a couple of paragraphs,’ ” Sommer says. “It was hard and difficult, and it was on Charlie’s terms.”
Ivanka passed the tests, and by 2009 Charles was ready to formally accept her into the Kushner family. At the couple’s wedding, which was held at the Trump National Golf Club in Bedminster, New Jersey, he stood up and, according to multiple sources, gave a toast that drew tears from the assembled guests. A person who attended the wedding recalls the central sentiments of the speech: “Look, everyone thinks she’s great, but being Jewish is just unbelievably important to us, and she’s not Jewish. It’s a problem for me, a genuine problem. Then I watched and got to see she’s in love with my son and it wasn’t what I thought in the beginning. I feel right about it.”

Trump stood up to speak after Charles, and he floundered miserably. According to one guest, he “gave the most pathetic, lame, embarrassing speech I’ve heard in a long time.”

People often talk about the Kushner brothers using similar adjectives: handsome, humble, diligent, polite, intelligent, and so forth. For Josh, however, unlike for Jared, there is no “but” hanging in the air, no comma before a caveat describing a barely perceptible undercurrent. Part of the reason is almost certainly the luck of age: When his father went to prison, Josh was a freshman at Harvard, where the scandal scarcely registered.

While Josh was still an undergraduate, his friend Daniel Kafie introduced him to Mario Schlosser, a German-born engineer who was studying at Harvard Business School. Schlosser had written code for a social network, and the three students decided to take it to market. They raised the money to launch the site, which they called Vostu, but after the company struggled to find an audience, Schlosser and Kushner had a fight about equity and refused to speak to each other for six months. In 2008, Schlosser realized that Vostu might be more successful as an online soccer game. He reconciled with Josh, who was by now at Harvard Business School, and built a new site. After a crashed server and a failed initial launch, the new iteration of Vostu, run out of Brazil, took off. “We started to make real money,” Schlosser says—about $10,000 a day.

Vostu’s success meant that Josh never had to seriously consider joining his brother in the family real estate firm. In 2009, he launched a venture fund called Thrive Capital with around $5 million from a group of individual investors including Joel Cutler, a mentor of Josh’s and the CEO of General Catalyst, a Boston venture-capital firm. It was a good start, but to be taken seriously, Thrive needed institutional money. Cutler soon introduced Josh to Andrew Golden, the president of Princo, Princeton’s endowment fund, which had a reputation for investing in young talent. According to Cutler, Josh and Golden hit it off right away. “There was just this tremendous belief that this young person would be able to attract other brilliant young people and do venture capital the right way.”

Once Princeton was on board, a roster of blue-chip investors quickly followed, including Yale, Duke, Harvard, Memorial Sloane Kettering, the Ford Foundation, and the Wellcome Trust. Instagram, the photography app, was an early success for the fund. In April 2012, Thrive joined four other firms in a $50 million funding round for the photo app. A few days later, Facebook purchased Instagram for $1 billion, a deal that doubled the value of Thrive’s investment. Other investments by the company include Warby Parker, Artsy, Spotify, Zola, Kickstarter, GitHub, and ClassPass.

Starting a game company and running an investment firm were not enough to satisfy Josh’s ambition.

It’s too early to tell whether the hype around Thrive is merely that. Yet Jon Winkelried, the co-CEO of TPG and former president of Goldman Sachs, says that the firm’s recent $700 million fundraising round, which brought Thrive’s total funds under management to $1.5 billion, is “big-boy stuff.” Kevin Ryan says, “If you called a bunch of entrepreneurs and said, ‘Who would you want to invest in your company in New York City?’ I think Union Square Ventures would be number one and I think Thrive would probably be number two already. That’s remarkable.” No one else, he says, has done it so young. “We just haven’t seen that.”

Josh’s ascent has necessitated a slow professional separation from his brother. Though Thrive is headquartered in the Puck Building, which is owned by the Kushner Companies, Jared has stopped making regular visits to his brother’s office. “I think there was a little source of tension with other partners at Thrive who felt like, you know, Jared swooning in and swooning out was not very constructive,” says one person close to the company. “I don’t think they very much liked it.” (Jared’s publicist says that he visits Thrive whenever he’s in the neighborhood, to give his brother “a hug and a kiss.”)

Starting a game company and running an investment firm were not enough to satisfy Josh’s ambition. In 2012, Mario Schlosser told Josh he needed to leave Brazil, and Vostu, to be with his wife, who was a researcher at Columbia University and pregnant with their first child. Schlosser says he blinked in disbelief when Josh suggested they start a health-insurance company. Josh explained that he had gone to the ER after spraining his ankle and had found the documentation required afterward difficult to navigate. He decided that health insurance needed to be made more consumer friendly. The idea, he said, was an online insurance provider that would be prepared for the day when individuals, not corporations and employers, were responsible for purchasing plans. He intended to call it Oscar Health, after his great-grandfather.

The timing was impeccable. Schlosser would later say that he and Josh couldn’t have made the company work without the Affordable Care Act, since the health-care landscape had been too “oligarchized” before the law’s passage. But as soon as the Supreme Court reaffirmed the central provisions of Obamacare, in the summer of 2012, Schlosser and his team were ready. Brian Singerman, a partner in the San Francisco–based Founders Fund, got interested in the company after Michael Ovitz sent him an email saying, “Trust me on this one.”

Josh Kushner has been dating supermodel Karlie Kloss since 2012.

Oscar has so far raised $728 million from investors, including Fidelity, Google Capital, Lakestar, and Khosla Ventures. Recent deals have valued the company at $2.7 billion, though The New York Times has questioned the wisdom of that number. (The Times noted that Oscar loses fifteen cents for every dollar it collects in premiums in New York.) Schlosser says it is still “very early days,” and, not surprisingly, he believes that from a sufficiently broad perspective his company is actually undervalued. “The U. S. health-care market alone is $3 trillion every year. That’s higher than Germany, the UK, Switzerland.”

Between running Thrive and Oscar, Josh Kushner has precious little spare time. “He is known, really, for just working,” says Kevin Ryan. “That’s all he does.” Nevertheless, Josh and Jared recently teamed up to launch an online real estate business called Cadre. The company’s mission is to create efficiency in a market that relies on a host of middlemen, but its prospects are still unclear even to some of its backers.

Schlosser says that Josh’s private life is rarely a subject of conversation. Years ago, at Harvard, Josh calmly explained the circumstances of his father’s scandal and his feelings about it, but in general the partners talk only about professional concerns—the ramifications for Oscar, say, of a Trump or a Clinton administration. Although Schlosser is not above the occasional joke about Jared’s role on the Trump campaign, he says that Josh tends to keep quiet about his personal life. “He has a girlfriend that he could talk about as well, but that is just so much less important.”

The girlfriend is supermodel Karlie Kloss, whom Josh has been dating for four years. According to Kenneth Pasternak, the future of the relationship is all but certainly being discussed by his parents. “They’d like him to settle down,” Pasternak says. No doubt Kloss would have to convert to Judaism, just as Ivanka Trump did. But whatever is in store for the relationship, it seems certain that Josh Kushner will not do anything that does not meet with the approval of his family.

Michael Ovitz says that Jared Kushner long ago made a deal with himself about how to publicly handle a familial bond with Donald Trump, a pact that meant no eye-rolling. “Donald was always controversial, always larger than life,” Ovitz says. “Jared knew that when he decided to marry Ivanka. But to both of them, it was understood that marriage meant loyalty to their in-laws. And incidentally, Jared discovered that he really liked Donald.”

Lately Jared’s liking of the Donald has morphed into something more substantial. Over the last year, Jared seems to have settled into a sort of hero worship, as though he wanted to become his father-in-law. His peers in the real estate industry talk about the stash of red “Make America Great Again” baseball caps that Jared keeps in his office, on the fifteenth floor of 666 Fifth Avenue. As he hands out the hats, he says of Trump’s slogan, “It came right out of his head!”

When Jared’s friends ask whether he endorses Trump’s anti-Muslim sentiments, he says, “You don’t understand what America is.”

Kevin Ryan, who is close with both brothers, breakfasted with Jared in early July. “He is all in,” he says. “He is in it to win.” Earlier this year, as Jared’s involvement in the campaign intensified, he named a president and a head of operations to run the family firm. The Observer has been enlisted as well: In advance of Trump’s appearance at AIPAC, Ken Kurson, the paper’s editor, reviewed the speech, causing an outcry in the newsroom. Despite these efforts, however, some have questioned whether Jared was fully prepared for the rigors and optics of a modern presidential campaign. In August, when several polls suggested that Trump’s chances for victory were cratering, Jared and Ivanka took a vacation. A series of photographs posted to Ivanka’s Instagram account showed the couple sightseeing in Croatia with Wendi Deng Murdoch, Rupert’s ex-wife.

A source close to Jared says that while he does not agree with every sentence that his father-in-law has uttered, he nevertheless thinks that Trump has been an effective candidate and would make a good president. (For his part, Trump said in a statement that “Jared represents the next generation of best-in-class developers and owners. Most importantly, however, he is a wonderful son-in-law, husband to my daughter, and father to my grandchildren.”) When his Jewish friends ask him—and they do—whether, given the history of the persecution of his own religion, Jared really endorses Trump’s anti-Muslim sentiments, he does not miss a beat justifying his father-in-law. “You don’t understand what America is,” he says, “or what American people think.”
Jared is especially proud of an article he wrote for the Observer in July, after his father-in-law’s Star of David tweet. It was a response to an open letter by Dana Schwartz, an entertainment writer for the paper, that had criticized Jared for standing “silent and smiling in the background” while Trump made “repeated accidental winks” to white supremacists. “You went to Harvard, and hold two graduate degrees,” Schwartz wrote. “Please do not condescend to me and pretend you don’t understand the imagery of a six-sided star when juxtaposed with money and accusations of financial dishonesty.”

In his response, Jared insisted that his father-in-law “is not anti-Semitic and he’s not a racist.” He defended Trump by detailing his grandparents’ harrowing experiences during the Holocaust. “It’s important to me that people understand where I’m coming from,” he wrote. “I know the difference between actual, dangerous intolerance versus these labels that get tossed around in an effort to score political points.”

(Given the contentiousness of the Kushner-family saga, it’s perhaps unsurprising that not all of his relatives appreciated his efforts. Two of his cousins complained on Facebook about his willingness to invoke their grandparents’ suffering to defend Donald Trump. “Thank you Jared for using something sacred and special to the descendants of Joe and Rae Kushner to validate the sloppy manner in which you’ve handled this campaign,” wrote Jacob Schulder, whose father, William, was the target of Charles Kushner’s retaliation in 2003. “Please don’t invoke our grandparents in vain just so you can sleep better at night. It is self-serving and disgusting.”)

Jared’s zealous support for Trump’s presidential campaign can be explained in part by a sense of loyalty that has been trained in him since birth, one way in which he and Ivanka are perfectly matched. Both have been raised in hermetically sealed family units—nearly every day the adult Trump children have lunch with each other in Trump Tower—and taught never to question their parents’ narratives in public, no matter how troubling they may be. When Trump’s anti-immigrant comments caused a number of companies to sever their ties with his properties, Ivanka told a source who commiserated with her about the damage to the Trump brand, “It’s his money. My father’s entire life has been a dream come true. He has to follow this dream.”

But many people who have dealt with Jared in the past suspect that his embrace of Trump’s political posturings carries a strong whiff of pure ambition. “How many people get that close to a presidential race?” asks Michael Fascitelli, Vornado’s former CEO and president. “In the real estate industry? Nobody, right?” And even if Trump were to lose in November by a large margin, he will nevertheless walk away from the election having won the support of a third or more of the American electorate. Whether Trump wins or loses, his son-in-law will almost certainly have a seat at the table. Jared is not one to waste a chance, and it seems unlikely that he will squander the entree into national consciousness that Trump’s campaign has given him.

“How many people get that close to a presidential race?”

Josh Kushner declined to comment on the record for this article; through a spokesman, he said that he loved his brother and did not want to say anything that might embarrass him. Nevertheless, the spokesman also said that Josh is a lifelong Democrat and will not be voting for Donald Trump in November.

Josh’s concern for his brother is no doubt genuine, yet more than one person has noted that he has little incentive to thwart even a distant chance at his family’s redemption. “He may not vote for Donald Trump,” observed a fellow real estate heir who knows the family well. “But will he be objecting to a pardon for his father, which is surely what will happen if Trump gets elected? I think not.”

The total rehabilitation of the Kushner family name would not, of course, mark the first time that money has bent the ordinary path of American justice. In many ways, the painting over of a family stain has become a rite of dynastic passage in the United States. But unlike, say, the family of financier Marc Rich, who secured a presidential pardon in the waning days of Bill Clinton’s presidency, the Kushners have exerted their influence in plain view, and with astonishing speed. None of us knows where it will all end. But Richard Mack has been warned.