In New York City, the second week of August 2006 was warm and mostly rainless, hospitable to the sort of al fresco promenades that often accompany film premieres. Jared Kushner attended two. Kushner was 25, a Harvard graduate, class of 2003. He had recently finished his third year in New York University’s JD/MBA program and had spent much of the summer at an enviable private-equity internship. Accompanying him to the Monday premiere of Trust the Man, a drama starring Julianne Moore, Eva Mendes, and Billy Crudup, was his then-girlfriend, Laura Englander, daughter of the hedge fund mogul Israel Englander. The glamour of the evening did not reflect the dominant mood of his recent years, which had been darkened by a sordid familial scandal—a crisis that had landed his father in prison and required him to abruptly shoulder the burdens of adulthood. But the worst of that ordeal seemed to be over, and for Kushner, the night came near the start of a kind of long, strange, coming-out party, which has yet to reach an end.

If the trappings of Hollywood felt new to Kushner, a native of suburban New Jersey, the company of corporate royalty did not. The eldest son of the billionaire real estate developer Charles Kushner, Jared had been his father’s protégé since childhood, trailing Charles to the apartment complexes that made up the Garden State real estate empire the elder Kushner had built from scratch. Charles, who goes by Charlie, was punctilious and ferociously driven—a marathoner who slept little and hung his ties in martial rows. Charismatic and deeply loyal to friends, he could also be tyrannical. Jared was more even-tempered, but he’d absorbed his father’s strict sense of discipline. For a job interview at 9 a.m., Charles once told him, “you leave at 6:00 and get there at 6:20 and sit there in a coffee shop until 9:00 waiting for the interview.”

Though Charles could seem austere in his habits, his public persona was defined by a self-regarding flamboyance that would prove to be a tragic flaw. His showiness often took the form of gift-giving. The Kushners were members of the Modern Orthodox community, and Jewish charities, as well as schools and synagogues, bore their name. A family friend once observed of Charles: “He loved that when he walks into a synagogue, the rabbis run over to him.” Beginning in the 1990s, Charles turned to politics, commencing a spree of fundraising and donations benefiting the Democratic Party. The effort amounted, over the course of a decade, to several million dollars—$1.5 million of it for the successful 2002 New Jersey gubernatorial campaign of Jim McGreevey.

Heavyweights including the Clintons and Bibi Netanyahu visited New Jersey to kiss the Kushner ring. Despite his talk about self-reliance, Charles didn’t hesitate to use donations to spare his first son the disappointments that might have otherwise awaited a young man of Jared’s abilities. An undistinguished student, Jared got into Harvard not long after his father pledged $2.5 million to the university. Charles also reportedly tapped the late New Jersey Sen. Frank Lautenberg, a substantial beneficiary of his largess, to ask Ted Kennedy to interface with Harvard on Jared’s behalf. (Jared’s younger brother, Joshua, followed him to Harvard five years later; he also has two sisters, Nicole and Dara.) Before Jared entered graduate school, Charles leased three floors of the Puck Building—a historic NoLita structure he’d bought in 1999—to NYU at sub-market rates.

But in 2004, the social ladder that Charles Kushner had constructed for his eldest son appeared to collapse. Charles pleaded guilty to 18 felony counts of tax evasion, witness tampering, and corruption-related charges, receiving a two-year prison term at sentencing the next year. The court proceedings originated with two lawsuits, filed by a former Kushner Cos. employee, in 2002 and 2003, alleging malfeasance in Charles’s political giving. Gov. McGreevey had recently nominated Charles, his faithful donor, to chair the board of the Port Authority, a position with significant oversight of development contracts. The coincidence attracted the notice of Chris Christie—then the U.S. attorney for New Jersey—who carried out an investigation into the matter with his characteristic gusto, perhaps augmented by the thought that with McGreevey gone, he might become the state’s next governor.

Tawdry in the extreme, the fiasco that followed played out like a subplot cut from the final edit of Crimes and Misdemeanors. A disagreement over business between Charles and his brother, Murray, had fractured their relationship not long before Christie’s investigation began. Charles believed Murray and their sister, Esther, who sided with Murray, were cooperating with the U.S. attorney’s office. (They were.) To retaliate, Charles enlisted a crooked cop, arranging to have Esther’s husband, with whom he had a longstanding feud, filmed in flagrante with a prostitute. He sent stills from the tape to Esther. Esther provided them to the FBI, whose agents considered them an attempt to intimidate government witnesses.

At 24, with his father incarcerated, Jared began helping to operate Kushner Cos. “He’s admired his father since he was a very young age,” Nitin Saigal, a close friend of Kushner’s from Harvard, told me recently. “There was never any negativity [about his father]. He realized very quickly that he had to be there for his family and focus on its business.” Almost every weekend, Kushner flew to Alabama to visit his father in prison. “I wouldn’t see him at all,” said Saigal, who was then sharing an apartment with Kushner in New York. “He understood that he had responsibilities bigger than himself.”

But by the time of the premiere in Chelsea, Charles had less than three weeks of jail time left, and Kushner was red-carpet-ready. Tall and slender, with a prep-school haircut and an eerily flawless complexion, he could, in the right light, resemble JFK. At the Frisch School, the yeshiva in Bergen County he’d attended, he had inspired a certain amount of swooning. Among movie stars, though, Kushner was a nobody. He and Saigal lived in an unremarkable rental on Mercer Street. Immersed in work, he didn’t involve himself in bleary nights or luxury car wrecks, as children of privilege sometimes do. His romantic life did not, as yet, interest Page Six. If the online archive of Getty Images is any indication, the photographers on hand to capture notables entering the premiere didn’t see anything notable about him: Its footage of the event contains no trace of Jared Kushner.

The oversight would not be repeated. About 10 days earlier, Kushner had purchased The New York Observer, reportedly paying nearly $10 million for the weekly newspaper, whose small circulation of about 50,000 belied its influence with prominent media, real estate, and political types, who valued the paper’s deep reporting and reliable snark. (Donald Trump—and Charles Kushner, during his turn in the legal spotlight—not infrequently received unfavorable attention from the paper’s writers.)

On the morning of the Chelsea premiere, an email went out advising the press that Kushner’s star was rising: “Updated Media Alert: Factotum premiere tomorrow!” Factotum, a film based on a novel by Charles Bukowski, was to screen the next day in the West Village—an affair co-hosted by the Observer. Marisa Tomei, Matt Dillon, Ally Sheedy, and “JARED KUSHNER, the 25-year-old new owner of the NY Observer,” would attend. Only the portion of the message related to Kushner appeared in bold. The bulletin worked. In Getty photos from the evening, Kushner poses in a tan blazer, smiling beside Tomei and Lili Taylor. “His dimples worked overtime, bewitching young female reporters,” one young female reporter wrote.

But for a man who’d just turned a spotlight on himself, Kushner seemed skittish. He parried even the most playful queries. Asked whether he had any vices, he replied, “I still haven’t figured out a way to answer these questions without really answering them.”

****

Soon, very soon, barring some succession of events so awful as to surpass even the insanely high bar set this season for civic unpleasantness, Donald Trump will be consigned to the dustbin of American political history. Unless the very real and deep problems that the country is facing today—the onward march of the billionaires, a collapsing press, the spreading effects of technologies that make large sections of the workforce redundant, the decline of American power abroad, a resurgence of identity politics at home, etc.—somehow prove fatally disorienting, he will go slouching back to Mar-a-Lago. Perhaps the specter of a Trump presidency will have a lingering salutary effect on both parties, and the political fevers will break, though probably not.

Other key questions will nevertheless remain. Among those pertinent here: What will become of Jared Kushner, the Trump campaign’s smooth-faced consigliere, who just last week broke his regular observance of the Sabbath for a strategy meeting in Trump Tower to help his father-in-law (in Yiddish, shver) deal with a tape of his extraordinarily vulgar remarks about women? Can his role be chalked up to a more-or-­less normal sense of loyalty and ambition? Does he remain the type of person that others want to do business with, or socialize with, even in New York? Or will Kushner be held responsible, in some important ways, for his role in his father-­in­-law’s campaign?

The Times has called Kushner a “de facto campaign manager” for Donald Trump, but in a campaign that often seems rudderless, his real value may be less managerial than sensory. Trump has moderated his tendency toward bigotry and misogyny only slightly since the beginning of election season, and recent revelations have made the change seem especially superficial. Kushner, on the other hand, is a normalizing presence. His hair is a normal color. He signals his aspirations legibly, without being garish. At cocktail parties, he is pleasant. For Trump, he has been an essential go-between—a kind of human balm, useful for preventing or soothing abrasions. Trump reportedly uses him exactly this way, deploying Kushner as an emollient with corporate and political figures, including Israeli ambassador Ron Dermer; Henry Kissinger; Mexican President Enrique Peña Nieto; Ronald Perelman; Paul Ryan, and numerous other Republican leaders. This past September, Kushner helped arrange a meeting between Trump and Netanyahu. A former associate of Rupert Murdoch recently told The New Yorker: “I think Jared’s been the key in getting Rupert to come around to the idea of a Trump presidency.”

But the question of what else there is to Jared Kushner remains somewhat mysterious. “It’s interesting, because [Kushner is] just like Trump in a way,” said Michael Gross, a journalist and author who has known Trump for many years. “He had this ambition to cross the river and make a mark. And yet he remained, and remains, something of a cipher. Obviously, the question is: Is there a there there?”

When Jared Kushner has talked on the record in the past, his reluctance to delve beneath the surface is such that it is often offered practically as his defining trait. Journalists reach for similar descriptions: “usually press-averse” (Fortune); “soft-spoken and restrained” (the Times); “he is … notoriously private” (Associated Press). Occasionally, a stonewalled reporter ventures an interpretation: “He often comes across as purposefully bland, as if he’s trying to discourage interest in his activities—or himself” (Businessweek). When associates speak for attribution, they’re almost invariably complimentary without much deepening the portrait: “He’s very humble and calm, always” (Asher Abehsera, a partner with Kushner in several Brooklyn developments, to Businessweek); “Besides being devastatingly handsome, he is well-mannered, well-bred, and so well-turned-out” (Peggy Siegal, a publicist, to Vanity Fair); “Jared is very smart and hardworking” (Steven Roth, CEO of Vornado Realty Trust, to The Real Deal). Bob Knakal, a chairman at the commercial real estate giant Cushman & Wakefield, told me, “He’s a very, very likable guy.”

Kushner does not discourage this view of himself, as a kind of responsible boy next door—perhaps a touch wide-eyed—who’s made good in the big city. “I didn’t expect the public side of this,” he said of owning the Observer not long after buying it, later adding, “I quickly learned that there really wasn’t much benefit to being [visible in the media]. … When I bought the paper, I had no idea the level of power and influence it had.” But many find such statements disingenuous. Bob Sommer, a former president of Observer Media Group, has said, “[Kushner] was definitely looking to make a reputation for himself quickly, and the newspaper was the opportunity that was there to be had.” Mitchell Moss, a professor of urban policy and planning at NYU and an acquaintance of Kushner’s, agrees. “Jared understands being a newspaper owner moves you into a different league,” he said in May. He later added, “He’s an intelligent and thoughtful young man and he has now surged to the political top through marriage.”

Indeed, owning the Observer granted Kushner status in areas of New York life in which the sons of disgraced New Jersey real estate barons don’t generally garner breathless adulation. Of their introduction, Ivanka Trump, whom Kushner wed in 2009, has said: “I knew about him in his capacity as the new owner of the Observer.” Soon after buying the paper, Kushner paid $1.8 billion for a 41-story commercial tower at 666 Fifth Avenue. At the time, it was the highest price ever paid for a Manhattan building, and the purchase has been widely interpreted as an amplified declaration of Kushner’s arrival in the city. In 2009, he and Ivanka appeared, as themselves, in an episode of Gossip Girl. Three years later, Kushner bid on the Los Angeles Dodgers in an unsuccessful attempt to become the youngest owner in Major League Baseball.

Since February, when he appeared onstage beside his wife, Ivanka Trump, in Manchester, New Hampshire, at a campaign event celebrating her father’s triumph in that state’s Republican presidential primary, Kushner has attracted considerable media interest. The New Yorker, Businessweek, Esquire, and others have run long profiles. None benefited from the subject’s cooperation. (Kushner also declined to participate in this piece.) For anyone seeking insight into Kushner’s understanding of the formative events of his short life, an interview he gave to New York in 2009 may remain the most revealing source. “[My father’s] siblings stole every piece of paper from his office, and they took it to the government,” he told the writer, Gabriel Sherman. “Siblings that he literally made wealthy for doing nothing. He gave them interests in the business for nothing. All he did was put the tape together and send it.”

Having no filial stake in the matter, the FBI saw things somewhat differently. In a 2009 press release, the bureau characterized Kushner Cos. as the locus of “a criminal conspiracy spanning the years 1997 to 2003,” involving numerous participants—and having nothing at all to do with the unfortunate videotape. Charles, for his part—much like Trump—has not appeared tormented by his conscience. Both Charles and Jared heap additional blame on the press, which they believe treated Charles unfairly.

In the Kushner calculus, regret and contrition become footnotes to enmity for witnesses and reporters—vendors of inconvenient facts. They seem to consider their hardship primarily a result of excessive revelation, or insufficient concealment, rather than the consequence of any underlying wrongdoing. Asked in an interview after his release what he might do differently, Charles said, “I don’t think I would change much. I probably would have heeded my father’s advice not to take my brother in as a business partner.”

***

Arthur L. Carter, the former investment banker who founded the New York Observer in 1987, did not run it as a business. When Kushner acquired it in 2006, the paper was losing an estimated $2 million annually. At the helm was Peter Kaplan, the paper’s longest-serving editor-in-chief and a revered figure among reporters. A rumpled presence with tortoise-shell glasses and a strong literary bent, Kaplan was known for nurturing young talent. “He presided over this wonderful journalistic sandbox,” said Michael L. Thomas, a novelist and longtime Observer columnist. “A lot of people cut their teeth there.” Among them were Sex and the City’s Candace Bushnell, New York Times reporter Warren St. John and New Yorker staff writer Nick Paumgarten. (I was an Observer staff writer between 2013 and 2015.)

Speaking to the Times about the sale, Kushner said much to inspire confidence among those who might have otherwise regarded the new owner with suspicion. “It is very simple: The second I play with the toy, it breaks,” he explained. “If I were to get involved in editorial decisions, the paper would not have the value it has.” Kaplan himself seemed reassured. “Chemically, I responded well to him,” he told the Times. “And when he said he would not interfere with the editorial process, I believed him.”

Beyond a few kind words for Kaplan, though, Kushner said little about the paper’s content, emphasizing its “elite readership” and “phenomenal brand,” while seeming only slightly familiar with the Observer itself. He appeared to view it coolly, as a badly-managed company with a solid name that he could leverage to turn its books from red to black. In journalism, an aloof owner is often preferable. But the reasons for Kushner’s reticence about the Observer soon became clearer: He didn’t like it. “I found the paper unbearable to read,” he told New York in 2009. “It was like homework.”

To address Kushner’s concerns, Kaplan collaborated with him on a tabloid redesign that accommodated a larger volume of shorter articles. Kushner envisioned it as “New York Post goes to college.” Some, however, found his taste incompatible with the paper’s traditions. He couldn’t believe that the elite readers he’d coveted were fond of the same articles he found boring. “Jared didn’t understand what made the Observer valuable,” a longtime editor who worked closely with Kaplan told me. “With the reconfiguration, it was almost like we had to have two things going on: communicate to the sophisticated audience that loved it, but also communicate to Jared in a form he could understand.”

Kaplan soon grew dismayed with pressure to reduce staff, and in April 2009, after 15 years at the paper, he announced that he would step down. Amid reports of clashes with ownership, two more editors-in-chief came and went in less than two-and-a-half years. Reporters fled or were dismissed en masse, all but emptying the bullpen of Kaplan disciples. Its voice diluted, the paper lost influence.

Kushner stopped appearing regularly in the office, and Christopher Barnes, an advertising executive hired as president shortly before Kaplan left, seemed to have his proxy. In a February 2011 report in Adweek, editorial staffers described a toxic office environment, accusing Barnes of taking pleasure in firings. To them, he seemed to consider journalism a kind of shabby scaffold on which to drape advertising. Whether or not Barnes felt that way, Kushner at least appeared to endorse his methods, employing him for almost four years.

But the same month as the Adweek story, cause for optimism materialized with the hiring of Elizabeth Spiers, the founding editor of Gawker, as editor-in-chief. “The change was clear immediately,” one former editor said of her arrival. “There was a sense of stability. We did not sit around talking—or thinking about—Jared Kushner. Elizabeth provided this incredible shield.”

Spiers did not respond to an interview request. But she has blogged about her editorship, and spoken about it on two podcasts. From two of her predecessors, she knew that Kushner’s devotion to editorial independence had proved disingenuous. Leery of giving offense, he favored anodyne, if not promotional, coverage of friends and associates. Spiers advised him that to be credible, the Observer had to resume the anatomizing evaluations of wealth and power it was known for. But Kushner was unconvinced. Spiers writes, “There were many, many occasions where Jared would go down the road of trying to kill a story,” though with one exception—a piece about a sale of an apartment—she was able to dissuade him from doing so.

Charles Kushner with his legal team and wife outside the U.S. District Courthouse August 18, 2004 in Newark, New Jersey, before he pleaded guilty to federal charges that he hired a prostitute to try to silence a witness in a federal investigation.(Photo by Chris Hondros/Getty Images)

Kushner seemed less shy, however, about attacking foes. In a widely-read blog post, Spiers describes what she calls “The Big Dick Mack Story”—an episode in which Kushner insisted, in the teeth of evidence, that Richard Mack, a real estate executive who he believed had wronged him, merited a hit piece. Spiers assigned one reporter to investigate, then two. In a subsequent meeting with Kushner and a source he touted as prime, Spiers and the reporters questioned the source. When none of these efforts surfaced wrongdoing, Kushner finally relented.

Spiers was followed as editor-in-chief in August 2012 by Aaron Gell. According to Gell, Kushner made no attempt to influence coverage during his tenure. But he remained dissatisfied with the Mack effort, and after six months, Gell was relieved of command to make room for Ken Kurson—a conservative political consultant and close family friend. Gell wrote me in an email that Kushner explained to him that although he had performed well, he “needed someone he ‘could trust.’ ”

Kurson swiftly sought to emphasize that the paper’s era of instability had ended, declaring in an early staff meeting his intention to “be buried” in an Observer T-shirt. He remains editor-in-chief, a role he has occupied longer than anyone other than Peter Kaplan and the paper’s first editor, John Sicher. (Kaplan died in 2013, at 59.) Soon after Kurson’s appointment, Kushner made a rare visit to the Observer offices. He had owned the paper for nearly seven years, during which he had changed it from a broadsheet to a tabloid, and back to a broadsheet. (He’s since made it a tabloid again.) But he still didn’t like reading it. Asked during a Q&A with staff to name some of his favorite recent articles, Kushner managed, after an awkward pause, to identify one story, about real estate. “I don’t really think I’m your target audience,” he said.

The persistent failure of the Observer’s content to please its owner may have had less to do with Kushner’s literary preferences than with the possibility that he has none. Several sources described him to me as an unenthusiastic reader, with little use for newspapers, let alone books. Under Kurson, the paper has become sleek, with clean design, plentiful luxury advertising, and often-fawning coverage of celebrities, socialites, and capitalists. Web traffic is up, and Kushner claims that the Observer is “cash-flow positive.” But though the paper still claims to reach an educated, high-net-worth audience, he has not so much leveraged the brand he bought from Arthur Carter as effaced it. Nowhere is this more apparent than on its website, where Real Housewives recaps keep company with the wounded, insult-laden rants of French journalist Jaques Hyzagi; strangely Kremlin-sympathetic blog posts; and the self-promotional columns of celebrity rabbi Shmuley Boteach, who himself goes elsewhere with his best material.

Even if he cannot be directly credited for any of these elements, Kushner’s guidance—or at least what has often appeared to be his guidance—has become less subtle during Kurson’s editorship. Soon after his arrival, Kurson summoned Kim Velsey, a real estate reporter, to his office, with a story to propose. The wife of a rival real estate scion, he said, was serially unfaithful. He described this as an open secret in society circles, and encouraged Velsey to firm up the rumor.

Relatively new to the paper, Velsey didn’t want to disappoint her boss, but she felt uncomfortable. The proposal seemed vindictive and scarcely relevant to her beat. She asked Jotham Sederstrom, then the editor-in-chief of the Observer’s sister commercial real estate publication, The Commercial Observer, for advice. Kurson had recently tried to interest Sederstrom in a story on Richard Mack, which Sederstrom declined to pursue, having heard about Mack from Spiers, to whom he is now married. (Kurson says that the Mack story he suggested was unrelated to the one Spiers looked into.) Sederstrom confirmed Velsey’s inclination to skip the adultery story, and Kurson ultimately dropped the issue. (Sederstrom does not specifically remember the conversation with Velsey, but doesn’t dispute her account; Kurson says he does not remember the incident at all.)

In 2014, the Observer ran a negative profile of New York Attorney General Eric Schneiderman, for which Kurson engaged Michael Craig, an Arizona-based author of two books on poker. Craig had also been hired a year earlier for a sprawling takedown of the Wilfs, a powerful New Jersey real estate clan. In at least the second case, Kurson, who mostly delegates editorial duties, maintained tight control, declining to show drafts to editors who otherwise handled features until near press time.

The Schneiderman story involved an additional twist. Inexplicably, Kurson assigned it first to a 28-year-old named Bill Gifford, the manager of a suburban ice cream parlor, who withdrew when he sensed it “was definitely meant to be negative.” Widely criticized, the piece included an extended critique of a lawsuit filed by Schneiderman against Donald Trump, having to do with his involvement in Trump University. Craig accorded Trump considerable space for an airing of grievances, named few other sources, and cited approvingly statistics supplied by a Trump-sponsored website.

A notable exception to anti-Observer media sentiment in the wake of the story was Jack Shafer, a respected older press critic, who defended it and, more broadly, the form of the “hatchet job,” writing in Reuters that among power players, “nobody should be indemnified from criticism just because it comes from a conflicted space.” In the Observer newsroom—where I had a desk at the time—embarrassment about the piece was widespread. For many, though, the profile’s bias caused less distress than its poor craftsmanship. In its indifference to journalistic standards, it could seem to imply disdain for the profession—or to badly misunderstand its purpose.

The fate of a January 2016 Commercial Observer cover story is less clear-cut. The piece concerned New York Community Bank, which the article’s author, Damian Ghigliotty, characterized as “the most prolific multifamily and commercial real estate lender in [New York City] over the past three years at least.” The profile, while neutral in tone, described the bank’s operation in dense detail, and noted that NYCB’s parent company, New York Community Bankcorp., had recently acquired Astoria Financial Corp., in a $2 billion deal that had yet to get shareholder approval.

When the piece ran, however, NYCB executives were unhappy. When contacted for comment this week, senior management at the bank insisted that the story contained inaccuracies, though did not immediately recall what they were. In any case, the bank’s honchos contacted Kushner about their displeasure, and took the unusual step of composing an alternate version of the story to replace the original on the Commercial Observer’s website. The replacement was never published, but the original was removed from the site. It’s unclear by whom. (Kurson, for his part, vehemently denies having anything to do with it.)

As Ghigliotty notes in the original story, of which I acquired a copy, Kushner Cos. “has worked with [NYCB] on more than $1 billion in debt since 2004.” The bank also has the commercial real estate finance firm Meridian Capital Group as one of its most important partners. Meridian, in turn, counts Kushner Cos. among its largest clients. New York Community Bank Corp. is a publicly traded company. According to NYCB’s website, the bank is “the largest thrift in the nation.”

***

Since Jared Kushner’s purchase of 666 Fifth Avenue, in 2007, Kushner Cos. has completed more than $14 billion worth of transactions and $7 billion in acquisitions. The firm’s portfolio contains more than 20,000 multifamily apartments, and 13 million square feet of commercial space, spread through the Northeast and Mid-Atlantic. In New York, Kushner’s holdings have grown rapidly, often through investment in areas from which other developers have shied—including Queens and the scruffy edge of DUMBO, Brooklyn, where, together with partners, Kushner is currently converting buildings formerly owned by the Jehovah’s Witnesses into a tech-centric mixed-use campus—where presumably the bright young things of Manhattan who despise his father-in-law will pay premium rates for the Kushner brand.

One prominent broker I spoke with, who works regularly with Kushner, told me that he considers Kushner’s ability to think creatively and holistically one of his greatest strengths. “They’re willing to think outside the box,” he said of Kushner Cos. “You saw what they did in DUMBO—some people thought it might happen, but a lot of guys were a little nervous, not really willing to step in.” Tenants like Etsy and WeWork—as well as a general uptick in neighborhood momentum—have so far borne out Kushner’s intuition.

I asked the broker how it was that Kushner’s delicate manner had not hindered him in the New York development industry, which is known to reward ruthless aggression. “They’re really very honest,” he said, again using the plural to refer to Kushner Cos., where Charles Kushner is reputed to retain significant power. “They always did what they said they were going to do—and they’re very thorough.” Bob Knakal, the Cushman & Wakefield chairman, concurred. “Some clients couldn’t tell the truth if their lives depended on it,” he said. “They do a lot of transactions, but they never have the same partner. [Kushner] often partners again with same companies. He has the nice-guy philosophy: Do the right thing even if nobody is watching.”

Discussing 666 Fifth Avenue in 2008, Kushner noted that although Brooks Brothers, a longtime tenant, had been paying below-market rent, he hadn’t renegotiated the company’s lease. “You have a lease, you have to respect the lease,” he said.

But it is not an ironclad policy. The guideline can become flexible, for example, when he deals with middle-class tenants, rather than with multinational retailers or development executives with whom he might wish to do future business.

Since 2012, Kushner has purchased several dozen buildings in the East Village, making Kushner Cos. one of the neighborhood’s largest landlords, with more than 500 residential units under management. Kushner bought many of the buildings from the developer Ben Shaoul, the owner of the Magnum Real Estate Group, and his co-investors, Westbrook Partners and Meadow Partners. When Shaoul, et. al. acquired them, the buildings were occupied largely by rent-stabilized tenants. By the time Kushner agreed to buy them, they were not.

Shaoul, whom Rosie Mendez, a City Council member representing the East Village, has called “a chronic bad actor,” and whom the real estate blog Curbed has given the honorific “Sledgehammer,” is a widely reviled figure in New York. He is known for driving rent-stabilized tenants from their homes with lawsuits, false eviction notices, and what housing advocates call “construction-as-harassment”: clouds of dust, all-hours noise, vanishing staircases, faulty utility service.

Kushner acquired other East Village buildings—plus some in Brooklyn—from the developer Stone Street properties. According to Brandon Kielbasa, director of organizing policy for the Cooper Square Committee, a neighborhood advocacy organization, Stone Street’s tactics are not dissimilar from those used by Shaoul, or by Steven Croman—arguably the city’s most notorious landlord—who currently faces a raft of civil charges.

“What we see with Kushner is a top-buyer for already worked-over portfolios,” said Kielbasa, who has helped to organize and arrange legal representation for Kushner tenants. “A lot of the buying that he does fits that model. The buildings won’t be completely empty, but there will have been at least some attempt to clear out rent-regulated tenants during prior ownership.” In view of Kushner’s preferred quarry, the New York City blog Gothamist dubbed him an “apex scavenger.”

The moniker is apt, particularly if you view the neighborhood as an environment in flux, with long-term inhabitants often unequipped to repel opportunistic invaders. Benjamin Dulchin is executive director of the Association for Neighborhood Housing and Development, a nonprofit. “[Kushner] is an important player in this ecosystem,” he told me. “It’s interesting that somebody with his monied pedigree is looking to buy these kinds of old-style, rent-stabilized buildings.”

Historically, such properties made for reliable but unexciting mom-and-pop-style business. But about 15 years ago, larger equity-backed developers entered the market, aiming, in the argot of the industry, to “maximize value,” initiating gut renovations to attract wealthier tenants and elevated rents. Dulchin said, “Often, that model of investment has meant a very aggressive strategy and bad outcomes for former tenants.”

Outcomes for both former and current tenants of the buildings Kushner bought from Shaoul have frequently been less than ideal. Even those who endured the previous owner’s trying tenure have often made been unhappy—rather than relieved—by Kushner’s stewardship, which is handled by his Westminster Management company. David Dupuis has lived in one of the buildings, on East Fourth Street, since 1983. After Kushner bought it in 2013, he told me, it was well-maintained for about six months. Then things deteriorated. Tenants say cooking gas and heat have been shut off for months at a time. They claim trash has been allowed to pile up and public areas have gone uncleaned. At one point, a rat infestation made a trip to garbage cans in the rear yard a perilous prospect. Tenants claim Westminster has often failed to meaningfully respond to complaints until lawyers get involved. (A Kushner representative had not responded to requests for comment at press time.)

Dupuis, an artist, recalled that when he moved to the neighborhood, it “looked like Berlin after the war.” But the property in which he lives had no vermin problem. According to Dupuis, a Mr. Schneider—a member of the family who then owned the apartment house—mopped the halls weekly, often regaling residents with neighborhood history.

With Kielbasa’s guidance, tenants from Dupuis’ building and another owned by Kushner, who were experiencing similar problems, organized to protest. At a meeting, they wondered about those first six months, which had been similarly smooth in the other building, and the seemingly incongruous negligence that followed. One attendee was a former Kushner Cos. employee. He suggested that in those early days, the developer had likely been using their buildings as models to entice prospective investors for future projects.

Dulchin was cautious not to equate Kushner with Shaoul or Croman. But in another pair of rent-stabilized buildings that he acquired in 2013, on East Second Street, tenants complain Kushner pursued an aggressive tenant-ejection campaign reminiscent of more brazenly predatory low-rent landlords. More than 70 percent of the buildings’ residents turned over during the first nine months of his ownership, a period of obstreperous construction work that collapsed ceilings, eroded floors, caused frequent irregularities in water supply, and violated building codes. Tenants said fixes came slowly. Meanwhile, lease termination notices were slipped under doors, and Kushner sued tenants who declined to leave, though at least some of them had the legal right to stay. Average rents nearly doubled. Former tenants of Kushner-owned buildings have allegedly had difficulty recouping security deposits.

Today, Westminster Management does not allow its few remaining rent-stabilized East Village tenants to use an online portal available to market-rate renters to request repairs and pay rent. Having been fined erroneously more than once for late payment, Dupuis called the Westminster office to suggest that his using the portal might make life easier for everyone. A Westminster employee told him that the portal was a “luxury amenity,” for which he did not qualify. (It’s worth noting that having such tiers of service is entirely legal, if not very neighborly.)

A ready supply of righteous indignation is an important requirement for a person in Kielbasa’s profession. But Kielbasa is also deeply thoughtful about—and palpably saddened by—the source of his pique. “Real estate cannot be divorced from idea that we need homes for regular people,” he said. “One of the things that makes us most concerned about Kushner is that it’s such a monied operation. It’s sort of like swimming in an aquarium with a great white shark. Even if it’s not sizing you up at the moment, it could turn toward you at any time.”

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Kushner last spoke publicly about his father-in-law’s presidential prospects in an interview with the Times, in April 2015, long before a Trump administration seemed like a serious possibility. His remarks were characteristically opaque: “If he did do it, he’d be great.” A year later, the Observer endorsed Trump in the Republican primary, in an editorial that ran to feature length without substantively enriching Kushner’s initial recommendation. (In a 2009 interview, Kushner cited the paper’s Obama endorsement in 2008 as his favorite editorial to date, regretting only that he’d had to forsake Hillary Clinton, of whom he was deeply fond; in 2012, the Observer endorsed Mitt Romney, censuring Obama for stoking “class warfare.”) The Trump endorsement sought to marginalize the same “media and cultural” elite that had thrilled to Peter Kaplan’s paper, accusing them of dwindling influence and opinions that had “become increasingly irrelevant.”

The article belittled “14-point proposals,” “SAT-like cramming,” and “policy details,” disdaining “political slogan,” in favor of “a vision and an attitude” and “faith and leadership.”

Donald Trump, his wife Melania Trump, daughter Ivanka Trump, and son-in-law Jared Kushner at a campaign rally on February 1, 2016 in Waterloo, Iowa.(Photo by Brendan Hoffman/Getty Images)

About a week earlier, reports had surfaced that Observer Editor Kurson, who is a former communications director for Rudy Giuliani, had helped craft a speech that Trump delivered to AIPAC in March. Kurson soon changed the Observer’s zero-Trump-coverage policy, allowing his reporters to write about The Donald as they did other White House hopefuls. He also approved an open letter by Observer entertainment writer Dana Schwartz, who chided Kushner for his Trump support in the wake of Trump’s use of anti-Semitic imagery in a tweet criticizing Hillary Clinton. Kushner responded, with an essay in the Observer titled “The Donald Trump I Know.”

Kushner’s answer to Schwartz echoes the endorsement’s contempt for “the media.” Kushner, who lives in a penthouse at the Trump Park Avenue, admonishes journalists for hermetic elitism, encouraging Schwartz and other reporters to “get out there and meet some of those people outside their ken.” He writes, “It doesn’t take a ton of courage to join a mob. What’s a little harder is to weigh carefully a person’s actions over the course of a long and exceptionally distinguished career.” Kushner does not mention, of course, that this same career (Trump’s) has been richly marbled with evidence of gross prejudice. And as the essay’s title indicates, his assessments, inevitably, are personal: “The difference between me and the journalists and Twitter throngs who find it so convenient to dismiss my father-in-law is simple. I know him and they don’t.”

Kushner goes on to suggest that one of the reasons the Observer’s website “has more than quadrupled its traffic over the last three-plus years is that we’ve been actively broadening our perspective.” But it’s not clear whether he sees a relationship between his effect on the paper and the waning of the credibility that once made it an influential organ. Besides being a political operative, Kurson is a journalist—a former contributing editor to Esquire—and he can occasionally betray ambivalence about his time atop the masthead. Matthew Kassel, a former staff writer, recently recalled a day when he and Kurson were sifting through the Observer’s print archive. They came upon an issue from the mid-1990s featuring work by Ron Rosenbaum, a writer associated with 20th-century New Journalism; Charles Bagli, now the lead real estate reporter at the Times; and the eminent late art critic Hilton Kramer. Kurson seemed saddened. Kassel remembered him saying, “Sometimes I feel like I’m presiding over this dying paper—like I’m killing it.” (When reached for comment, Kurson did not deny saying this.)

In an interview with the podcast Story In a Bottle earlier this year, Elizabeth Spiers expressed sympathy for Kurson—and for Kushner, too. Her Observer editorship had coincided with another, shorter-lived, Trump presidential campaign, and she remembered Kushner’s insistence that the paper cover Trump “neutrally,” which she considered more or less impossible. After a particularly acrimonious conversation with Kushner, Spiers called a mutual friend. “[The friend] said something interesting,” she said. “‘You’re both sticking to your values. He’s thinking about this as an issue of family loyalty. You’re thinking about this as an issue of journalistic integrity.’”

Even before his father was betrayed by his siblings, and Kushner started giving up weekends to visit him in prison, loyalty was a defining personal trait. Nitin Saigal, Kushner’s Harvard classmate, told me that in Cambridge, Kushner often tried to bring friends into a kind of extended familial fold, inviting them to Hillel and Chabad, where he took many of his meals. Saigal’s family lived in Bombay, and the Kushners acted as surrogates, including him in dinners and lunches when they were in town, and hosting him in New Jersey during holidays. After college, during a trip to Asia, Saigal became sick with typhoid fever in Bangkok, and Kushner stayed with him until Saigal’s parents could get there. When Saigal was hospitalized for a virus in New York a few years later, Kushner did the same.

But the trouble with loyalty, of course, is that it is exclusive—a way of circumscribing experience. In the extreme, it can make inconvenient the kinds of abstractions that add up to things like law and ethics.

Not long after he purchased 666 Fifth Avenue, it became clear that Kushner had likely been overzealous—buying at the top of the market and perhaps over-leveraging the family shop to do so. To avoid losing control of the building, he sold a 49 percent stake to Vornado Realty Trust in 2011, in a deal that valued the tower at $820 million—nearly $1 billion less than he’d paid for it. According to Esquire, Vornado and Kushner Cos. have lately been at odds over how to most profitably use the space, with meetings between them often becoming “shouting matches” in which, according to one source, “most of the screaming is done by Charles Kushner.”

Back in 2008, the building was still an untarnished trophy, and Jared Kushner gave a long walking Q&A there to Conde Nast Portfolio. Speaking to the journalist Lloyd Grove, he enthused about the surfaces of things, pointing to a sculpture by the artist Isamu Noguchi and to the wooden facades of walls, critiquing the play of light on granite. In the Kushner Cos. lobby, on the 15th floor, he directed Grove’s attention to a framed photograph depicting a page from A Tale of Two Cities, Charles Dickens’s novel of class conflict in Paris and London.

In the transcript, Grove seems to register surprise: “Tale of Two Cities?” But the source—its epic story—did not much interest Kushner, who had made an odd, narrow reading of the text. The page was the novel’s first, and he was concerned only with its first line.

“That’s where it’s from,” he said. “But I love how we bought this building literally right after my father came out of prison … and the thought that I had was, it’s kind of like the juxtaposition of going from the worst of times to the best of times. How you never want to break a record, paying the biggest price, but to think that five months earlier, we were living through my father being in prison, and then, coming out and together buying the largest single asset.” The page photographed, Grove noted, was dog-eared, as if the reader, having taken from it all he wanted, had closed the book, and declined to go on.

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